1,2,3-Triazole synthesis
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Synthesis of 1,2,3-triazoles
Name Reactions
Recent Literature
The synthesis of 1-monosubstituted aryl 1,2,3-triazoles was achieved in good
yields using calcium carbide as a source of acetylene. The copper-catalyzed
1,3-dipolar cycloaddition reactions were carried out without nitrogen protection
and in a MeCN-H2O mixture.
Y. Jiang, C. Kuang, Q. Yang, Synlett, 2009,
p-TsOH is a vital additive in the 1,3-dipolar cycloaddition of
nitroolefins and sodium azide. This p-TsOH-mediated cycloaddition enables
a rapid synthesis of valuable 4-aryl-NH-1,2,3-triazoles in high yields.
X.-J. Quan, Z.-H. Ren, Y.-Y. Wang, Z.-H. Guan, Org. Lett.,
A highly efficient and effective synthesis of N-unsubstituted
4-aryl-1,2,3-triazoles is promoted by Amberlyst-15. The ion exchange resin can
be recycled and reused up to eight times without loss of catalytic activity.
H. Zhang, D.-Z. Dong, Z.-L. Wang,
Synthesis, 2016, 48, 131-135.
A Pd-catalyzed synthesis of 1H-triazoles from alkenyl halides and
sodium azide represents a completely new reactivity pattern in the context of Pd
chemistry.
J. Barluenga, C. Valdés, G. Beltrán, M. Escribano, F. Aznar, Angew. Chem. Int. Ed., 2006, 45, .
J. Barluenga, C. Valdés, G. Beltrán, M. Escribano, F. Aznar, Angew. Chem. Int. Ed., 2006, 45, .
A regioselective one-pot synthesis of 1,5-disubstituted 1,2,3-triazoles through
N/C-heterocyclization of allenylindium bromide across aryl azides is carried out
under mild conditions in aqueous medium and proceeds in good yields.
A. H. Banday, V. J. Hruby,
Synlett, 2014, 25, .
A tandem catalysis protocol based on decarboxylative coupling of alkynoic acids
and 1,3-dipolar cycloaddition of azides avoids usage of gaseous or highly
volatile terminal alkynes, reduces handling of potentially unstable and
explosive azides to a minimum, and furnishes various functionalized
1,2,3-triazoles in excellent yields and a very good purity without the need for
additional purification.
A. Kolarovič, M. Schnürch, M. D. Mihovilovic, J. Org. Chem., 2011,
Self-assembly of copper sulfate and a poly(imidazole-acrylamide) amphiphile
provides a highly active, reusable, globular, solid-phase catalyst for click
chemistry. The insoluble amphiphilic polymeric imidazole Cu catalyst drove the
cycloaddition of various of alkynes and organic azides at very low catalyst
loadings and can be readily reused without loss of activity to give the
corresponding triazoles quantitatively.
Y. M. A. Yamada, S. M. Sarkar, Y. Uozumi, J. Am. Chem. Soc., 2012,
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3-dibromopropanoic
acids and sodium azide by using inexpensive copper(I) iodide as the catalyst in
the presence of cesium carbonate as base and DMSO as solvent.
Y. Jiang, C. Kuang, Q. Yang, Synthesis, 2010,
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3-dibromopropanoic
acids and sodium azide by a one-pot method using N,N-dimethylformamide as
solvent in the presence of Pd2(dba)3 and Xantphos.
W. Zhang, C. Kuang, Q. Yang, Synthesis, 2010,
1-Substituted-1,2,3-triazoles were conveniently synthesized from the
corresponding aromatic and aliphatic azides in the presence of acetylene gas
using mild, copper(I)-catalyzed ‘click chemistry'.
L.-Y. Wu, Y.-X. Xie, Z.-S. Chen, Y.-N. Niu, Y.-M. Liang, Synlett, 2009,
A true Click catalytic system is based on commercially available [CuBr(PPh3)3].
This system is active at room temperature, with catalyst loadings of 0.5 mol %
or less, in the absence of any additive, and it does not require any
purification step to isolate pure triazoles.
S. Lal, S. Díez-González, J. Org. Chem., 2011,
Acid-Base Jointly Promoted Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
C. Shao, X. Wang, Q. Zhang, S. Luo, J. Zhao, Y. Hu, J. Org. Chem., 2011,
A well-defined copper(I) isonitrile complex is an efficient, heterogeneous
catalyst for azide-alkyne cycloadditions and three-component
reactions of halides, sodium azide and alkynes to form 1,4-disubstituted
1,2,3-triazoles in high yields under mild conditions in water. The complex can
be recycled for at least five runs without significant loss of activity by
simple precipitation and filtration.
M. Liu, O. Reiser, Org. Lett., 2011,
Cycloadditions of copper(I) acetylides to azides and nitrile oxides provide
ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted
isoxazoles, respectively. The process is highly reliable and exhibits an
unusually wide scope with respect to both components. Computational studies
revealed a nonconcerted mechanism involving unprecedented metallacycle
intermediates.
F. Himo, T. Lovell, R. Hilgraf, V. V. Rostovtsev, L. Noodleman, K. B. Sharpless,
V. V. Fokin, J. Am. Chem. Soc., 2005,
127, 210-216.
An efficient I2/TBPB mediated oxidative formal [4 + 1] cycloaddition
of N-tosylhydrazones with anilines represents a simple, general, and
efficient approach for the construction of 1,2,3-triazoles under metal-free and
azide-free conditions.
Z.-J. Cai, X.-M. Lu, Y. Zi, C. Yang, L.-J. Shen, J. Li, S.-Y. Wang, S.-J. Ji, Org. Lett.,
A mild, zinc-mediated method for regioselective formation of 1,5-substituted
1,2,3-triazoles from a wide range of azides and alkynes works at room
temperature. Additionally, the triazole 4-position can be further functionalized
by reaction of the intermediate aryl-zinc with various electrophiles to
accommodate a diverse three-component coupling strategy.
C. D. Smith, M. F. Greaney, Org. Lett., 2013,
N3-Alkylation of 1-(pivaloyloxymethyl)-1,2,3-triazoles with alkyl triflates,
followed by a nucleophile-promoted N1-dealkylation of the resulting strongly
electrophilic intermediate triazolium salts, provides 1,5-disubstituted
1,2,3-triazoles.
Z. Monasterio, A. Irastorza, J. I. Miranda, J. M. Aizpurua, Org. Lett.,
2016, 18, .
A Ce(OTf)3-catalyzed [3 + 2] cycloaddition of organic azides with
nitroolefins and subsequent elimination reaction selectively produces
1,5-disubstituted 1,2,3-triazoles in very good yields. Both benzyl and phenyl
azides react with a broad range of aryl nitroolefins containing a wide range of
functionalities.
Y.-C. Wang, Y.-Y. Xie, H.-E. Qu, H.-S. Wang, Y.-M. Pan, F.-P. Huang, J. Org. Chem., 2014,
1,5-Diarylsubstituted 1,2,3-triazoles are formed in high yield from aryl
azides and terminal alkynes in DMSO in the presence of a catalytic amount of
tetraalkylammonium hydroxide or t-BuOK for base-labile substrates. The
reaction is experimentally simple, does not require a transition-metal catalyst,
and is not sensitive to atmospheric oxygen and moisture.
S. W. Kwok, J. R. Fotsing, R. J. Fraser, V. O. Rodinov, V. V. Fokin, Org. Lett., 2010,
The use of t-BuOK in wet DMF as desilylating reagent in a cycloaddition
reaction of aromatic azides and trimethylsilyl alkynes generated
1,5-disubstituted 1,2,3-triazoles regioselectively in good yields at ambient
temperature.
L. Wu, X. Chen, M. Tang, X. Song, G. Chen, X. Song, Q. Lin, Synlett, 2012, 23,
A Cu/Pd transmetalation relay catalysis enables a three-component click reaction
of azide, alkyne, and aryl halide to yield 1,4,5-trisubstituted 1,2,3-triazoles
in one step in high yields with complete regioselectivity. This reaction offers
an alternative to the well-established CuAAC click reactions only working on
terminal alkynes.
F. Wei, H. Li, C. Song, Y. Ma, L. Zhou, C.-H. Tung, Z. Xu, Org. Lett.,
In the presence Cp*RuCl(PPh3)2 or Cp*RuCl(COD) as catalyst,
primary and secondary azides react with a broad range of terminal alkynes
containing a range of functionalities selectively producing 1,5-disubstituted
1,2,3-triazoles. Both complexes also promote the cycloaddition reactions of
organic azides with internal alkynes, providing access to fully-substituted
1,2,3-triazoles.
B. C. Boren, S. Narayan, L. K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V.
V. Fokin, J. Am. Chem. Soc., 2008,
In the presence of inexpensive copper (I) iodide as the catalyst, a series of
1,4-disubstituted 1,2,3-triazoles were synthesized in a one-pot process from
anti-3-aryl-2,3-dibromopropanoic acids and organic azides in dimethyl
sulfoxide.
X. Chen, Y. Yang, C. Kuang, Q. Yang, Synthesis, 2011,
A copper(I)-catalyzed three-component reaction of amines, propargyl halides and
azides forms 1-substituted-1H-1,2,3-triazol-4-ylmethyl)-dialkylamines in
water. Synthetic advantages are high atom economy, low environmental impact,
atmospheric oxygen, wide substrate scope, mild reaction condition and good
Z.-Y. Yan, Y.-B. Zhao, M.-J. Fan, W.-M. Liu, Y.-M. Liang, Tetrahedron, 2005,
A method for the regiospecific synthesis of
1,4,5-trisubstituted-1,2,3-triazole catalyzed by copper(I) iodide was developed.
This is the first example of a regiospecific synthesis of
5-iodo-1,4-disubstituted-1,2,3-triazole, which can be further elaborated to a
range of 1,4,5-trisubstituted-1,2,3-triazole derivatives.
Y.-M. Wu, J. Deng, Y. L. Li, Q.-Y. Chen, Synthesis, 2005,
Inexpensive copper catalysts enabled modular one-pot multicomponent syntheses
of fully decorated triazoles through a sustainable “click” reaction/direct
arylation sequence.
L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett.,
L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett.,
Microwave irradiation significantly enhances the rate of formation of
1,4-disubstituted 1,2,3-triazoles from alkynes and in situ generated azides.
Azides are derived from an efficient one-pot azidation of anilines with the
reagent combination t-BuONO and TMSN3.
A. D. Moorhouse, J. E. Moses, Synlett, 2008,
A reliable and operationally simple one-pot reaction for a one-carbon
homologation of various aldehydes followed by Cu-catalyzed azide-alkyne click
chemistry gives 1,4-disubstituted 1,2,3-triazoles in good yields without the
need for isolation of the alkyne intermediates.
D. Luvino, C. Amalric, M. Smietana, J.-J. Vasseur, Synlett, 2007,
1,2,3-Triazoles were prepared in good to modest yields by cycloaddition of
alkyl azides onto enol ethers under solventless conditions. The reaction can
access ring-fused triazoles that are unavailable by azide-alkyne cycloadditions
and is easily scalable. The 1,2,3-triazole products bear functionality that may
be readily derivatized.
D. R. Rogue, J. L. Neill, J. W. Antoon, E. P. Stevens, Synthesis, 2005, .
Triazoles have been synthesized via a three-component coupling reaction of
unactivated terminal alkynes, allyl carbonate, and trimethylsiyl azide under
Pd(0)-Cu(I) bimetallic catalysis. The deallylation of the resulting
allyltriazoles is described.
S. Kamijo, T. Jin, Z. Huo, Y. Yamamoto, J. Am. Chem. Soc., 2003, 125, .
Copper(I)-Catalyzed Three-Component Click/Alkynylation: One-Pot Synthesis of
5-Alkynyl-1,2,3-triazoles
W. Wang, F. Wei, Y. Ma, C.-H. Tung, Z. Xu, Org. Lett.,
2016, 18, .
Reaction of 4-bromo-NH-1,2,3-triazoles with alkyl halides in the presence
of K2CO3 in DMF produced the corresponding 2-substituted
4-bromo-1,2,3-triazoles in a regioselective process. Subsequent Suzuki
cross-coupling reaction provided an efficient synthesis of 2,4,5-trisubstituted
triazoles, whereas hydrogenation furnished an efficient synthesis of
2,4-disubstituted triazoles.
X.-j. Wang, K. Sidhu, L. Zhang, S. Campbell, N. Haddad, D. C. Reeves, D.
Krishnamurthy, C. H. Senanayake, Org. Lett., 2009,
The three-component reactions of enaminones, tosylhydrazine and primary amines
enabled a regioselective construction of 1,5-disubstituted 1,2,3-triazoles via
cascade dual C-N bond formation, N-N bond formation and an acyl migration-based
C-C bond formation. This metal- and azide-free method proceeds in the presence
of only molecular iodine.
J.-P. Wan, S. Cao, Y. Liu, J. Org. Chem.,
A palladium-catalyzed and ultrasonic promoted Sonogashira coupling/1,3-dipolar
cycloaddition of acid chlorides, terminal acetylenes, and sodium azide in one
pot enables an efficient synthesis of 4,5-disubstituted-1,2,3-(NH)-triazoles in
excellent yields.
J. Li, D. Wang, Y. Zhang, J. Li, B. Chen, Org. Lett., 2009,
TBAF-catalyzed [3 + 2] cycloadditions of 2-aryl-1-cyano- or
2-aryl-1-carbethoxy-1-nitroethenes with TMSN3 under solvent free
conditions allow the preparation of 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles under mild reaction conditions with good to excellent yields.
D. Amantini, F. Fringuelli, O. Piermatti, F. Pizzo, E. Zunino, L. Vaccaro, J. Org. Chem., 2005, 70, .
D. Amantini, F. Fringuelli, O. Piermatti, F. Pizzo, E. Zunino, L. Vaccaro, J. Org. Chem., 2005, 70, .
Triazole-based monophosphine ligands have been prepared via efficient
cycloadditions. Palladium complexes derived from these ligands are highly
active catalysts for Suzuki-Miyaura coupling and amination reactions of aryl
chlorides.
D. Liu, W. Gao, Q. Dai, X. Zhang, Org. Lett.,
2005, 7, .
A highly efficient method for the synthesis of multisubstituted 1,2,3-triazoles
via a direct Pd-catalyzed C-5 arylation has been developed.
S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org. Lett., 2007,
The use of nontoxic polyethylene glycol (PEG) as solvent and MesCO2H
as cocatalyst enabled user-friendly palladium(0)-catalyzed C-H bond
functionalizations under air in the absence of phosphine ligands. Direct
arylations of 1,2,3-triazoles gave substituted triazoles in good yields.
Recycling of the catalytic system led to a slight decrease of activity.
L. Ackermann, R. Vicente, Org. Lett., 2009,
Conditions for the palladium-catalyzed direct arylation of a wide range of
heterocycles with aryl bromides employ a stoichiometric ratio of both coupling
partners, as well as a substoichiometric quantity of pivalic acid, which results
in significantly faster reactions. An evaluation of the influence of the nature
of the aryl halide has also been carried out.
B. Liégault, D. Lapointe, L. Caron, A. Vlassova, K. Fagnou, J. Org. Chem., 2009,
A copper-catalyzed [3 + 2] cycloaddition/oxidation reaction of nitro-olefins
with organic azides affords a broad range of 1,4(-NO2),5-trisubstituted
1,2,3-triazoles with high regioselectivities and in very good yields without
elimination of HNO2.
Y. Chen, G. Nie, Q. Zhang, S. Ma, H. Li, Q. Hu, Org. Lett.,
A ruthenium-catalyzed cycloaddition of N-Boc ynamides with azides gives
protected 5-amino-1,2,3-triazole-4-carboxylic acids, which are suitable for the
preparation of peptidomimetics. When aryl or alkyl azides are reacted with N-Boc-aminopropiolates
or arylynamides, the cycloaddition occurs with complete regiocontrol, while N-Boc-alkyl
ynamides yield a mixture of regioisomers.
S. Ferrini, J. Z. Chandanshive, S. Lena, M. C. Franchini, G. Giannini, A. Tafi,
M. Taddei, J. Org. Chem.,
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Part I: 碳原子 Carbon
- I.1: 碳-碳键 Carbon-Carbon Bonds
&- I.1.1 烷烃 Alkanes
&&- 伯碳原子 Primary carbon
&&- 仲碳原子 Secondary carbon
&&- 叔碳原子 Tertiary carbon
&&- 季碳原子 Quaternary carbon
&- I.1.2 碳-碳双键和三键 C-C double and Triple Bonds
&&- 烯烃 Alkene
&&- 炔烃 Alkyne
&&- 累积二烯烃 Allene
- I.2: 含一个碳-杂键 One Carbon-Hetero Bond
&- I.2.1 卤代烃 Alkyl Halogenides
&&- 氯代 Alkylchloride
&&- 氟代 Alkylfluoride
&&- 溴代 Alkylbromide
&&- 碘代 Alkyliodide
&- I.2.2 醇和醚 Alcohols and Ethers
&&- 醇 Alcohol
&&- 伯醇 Primary alcohol
&&- 仲醇 Secondary alcohol
&&- 叔醇 Tertiary alcohol
&&- 二烷基醚 Dialkylether
&&- 二烷基硫醚 Dialkylthioether
&&- 烷基芳基醚 Alkylarylether
&&- 二芳基醚 Diarylether
&&- 烷基芳基硫醚 Alkylarylthioether
&&- 二芳基硫醚 Diarylthioether
&&- 氧鎓盐 Oxonium
&- I.2.3 胺类 Amines
&&- 胺 Amine
&&- 脂肪伯胺 Primary aliphatic amine
&&- 脂肪仲胺 Secondary aliphatic amine
&&- 脂肪叔胺 Tertiary aliphatic amine
&&- 脂肪季铵盐 Quaternary aliphatic ammonium
&&- 芳香伯胺 Primary aromatic amine
&&- 芳香仲胺 Secondary aromatic amine
&&- 芳香叔胺 Tertiary aromatic amine
&&- 芳香季铵盐 Quaternary aromatic ammonium
&&- 混合仲胺 Secondary mixed amine
&&- 混合叔胺 Tertiary mixed amine
&&- 混合季铵盐 Quaternary mixed ammonium
&&- 铵盐 Ammonium
&- I.2.4 其他含一个碳杂键 Others
&&- 巯基 Alkylthiol
&&- 二烷基硫醚 Dialkylthioether
&&- 烷基芳基硫醚 Alkylarylthioether
&&- 二硫化物 Disulfide
&&- 1,2-氨基醇 1,2-Aminoalcohol
&&- 1,2-邻二醇 1,2-Diol
&&- 1,2-偕二醇 1,1-Diol
&&- 氢过氧化物 Hydroperoxide
&&- 过氧化物 Peroxo
&&- 有机锂化合物 Organolithium compounds
&&- 有机镁化合物 Organomagnesium compounds
&&- 金属有机化合物 Organometallic compounds
- I.3: 含两个碳-杂键（羰基及衍生物） Two Carbon-Hetero Bonds (Carbonyl and Derivatives)
&- I.3.1 碳-杂双键 Double Bond to Hetero
&&- 醛 Aldehyde
&&- 酮 Ketone
&&- 硫醛 Thioaldehyde
&&- 硫酮 Thioketone
&&- 亚胺 Imine
&&- 亚胺盐 Immonium
&&- 肟 Oxime
&&- 肟醚 Oximether
&- I.3.2. 两个碳-杂单键 Two Single Bonds to Hetero
&&- 缩醛 Acetal
&&- 半缩醛 Hemiacetal
&&- 缩醛胺 Aminal
&&- 半缩醛胺 Hemiaminal
&&- 硫缩醛 Thioacetal
&&- 硫半缩醛 Thiohemiacetal
&&- 卤代缩醛 Halogen acetal like
&&- 其他类缩醛 Acetal like
&&- 卤代甲基醚 Halogenmethylen ester and similar
&&- 氮、氧、硫代甲基醚 NOS methylen ester and similar
&&- 其他杂代甲基醚 Hetero methylen ester and similar
&&- 羟腈 Cyanhydrine
&- I.3.3 两个碳-杂键接碳-碳双键（类似烯醇） Single Bond to Hetero, C=C Double
Bond (Enols and Similar)
&&- 氯代烯烃 Chloroalkene
&&- 氟代烯烃 Fluoroalkene
&&- 溴代烯烃 Bromoalkene
&&- 碘代烯烃 Iodoalkene
&&- 烯醇 Enol
&&- 烯二醇 Endiol
&&- 烯醇醚 Enolether
&&- 烯醇脂 Enolester
&&- 烯胺 Enamine
&&- 烯硫醇 Thioenol
&&- 烯硫醚 Thioenolether
- I.4: 含三个碳-杂键（羧基衍生物） Three Carbon-Hetero Bonds (Carboxyl and Derivatives)
&&- 酰氯 Acylchloride
&&- 酰氟 Acylfluoride
&&- 酰溴 Acylbromide
&&- 酰碘 Acyliodide
&&- 酰卤 Acylhalide
&&- 羧酸 Carboxylic acid
&&- 羧酸酯 Carboxylic ester
&&- 内酯 Lactone
&&- 酸酐 Carboxylic anhydride
&&- 羧酸衍生物 Carboxylic acid derivative
&&- 硫代羧酸 Carbothioic acid
&&- 硫代羧酸(硫)酯 Carbothioic S ester
&&- 硫代羧酸(硫)内酯 Carbothioic S lactone
&&- 硫代羧酸(氧)酯 Carbothioic O ester
&&- 硫代羧酸(氧)内酯 Carbothioic O lactone
&&- 硫代羧酸酰卤 Carbothioic halide
&&- 二硫代羧酸 Carbodithioic acid
&&- 二硫代羧酸酯 Carbodithioic ester
&&- 二硫代羧酸内酯 Carbodithiolactone
&&- 酰胺 Amide
&&- 伯酰胺 Primary amide
&&- 仲酰胺 Secondary amide
&&- 叔酰胺 Tertiary amide
&&- 内酰胺 Lactam
&&- 烷基酰亚胺 Alkyl imide
&&- 氮杂酰亚胺 N hetero imide
&&- 酰亚胺(酸性) Imide acidic
&&- 硫代酰胺 Thioamide
&&- 硫代内酰胺 Thiolactam
&&- 肟酯 Oximester
&&- 脒(不属于芳香环一部分) Amidine
&&- 羟肟酸 Hydroxamic acid
&&- 羟肟酸酯 Hydroxamic acid ester
&&- 亚氨酸 Imidoacid
&&- 环亚氨酸 Imidoacid cyclic
&&- 亚氨酸酯 Imidoester
&&- 亚氨酸内酯 Imidolactone
&&- 硫代亚氨酸 Imidothioacid
&&- 硫代环亚氨酸 Imidothioacid cyclic
&&- 硫代亚氨酸酯 Imidothioester
&&- 硫代亚氨酸内酯 Imidothiolactone
&&- 脒(非(硫代)羰基取代且不属于环结构) Amidine
&&- 亚氨酸内酰胺 Imidolactam
&&- 亚氨酸酰卤 Imidoylhalide
&&- 环亚氨酸酰卤 Imidoylhalide cyclic
&&- 氨基腙 Amidrazone
&&- Alpha-氨基酸 Alpha aminoacid
&&- Alpha-羟基酸 Alpha hydroxyacid
&&- 肽键 Peptide middle
&&- 多肽碳端 Peptide C term
&&- 多肽氮端 Peptide N term
&&- 原羧酸酯 Carboxylic orthoester
&&- 烯酮 Ketene
&&- 烯醛 Ketenacetal
&&- 腈 Nitrile
&&- 异腈 Isonitrile
&&- 共轭羰基及衍生物 Vinylogous carbonyl or carboxyl derivative
&&- 共轭羧酸 Vinylogous acid
&&- 共轭羧酸酯 Vinylogous ester
&&- 共轭酰胺 Vinylogous amide
&&- 共轭酰卤 Vinylogous halide
- I.5: 含四个碳-杂键（碳酸衍生物） Four Carbon-Hetero Bonds (Carbonic Acid and Derivatives)
&&- 碳酸二酯 Carbonic acid dieester
&&- 碳酸脂酰卤 Carbonic acid esterhalide
&&- 碳酸单酯 Carbonic acid monoester
&&- 碳酸衍生物 Carbonic acid derivatives
&&- 硫代碳酸二酯 Thiocarbonic acid dieester
&&- 硫代碳酸脂酰卤 Thiocarbonic acid esterhalide
&&- 硫代碳酸单脂 Thiocarbonic acid monoester
&&- 脲 Urea
&&- 硫脲 Thiourea
&&- 异脲 Isourea
&&- 异硫脲 Isothiourea
&&- 胍 Guanidine
&&- 氨基甲酸 Carbaminic acid
&&- 氨基甲酸酯 Urethan(Carbamate ester)
&&- 缩二脲 Biuret
&&- 氨基脲 Semicarbazide
&&- 碳酰肼 Carbazide
&&- 缩氨基脲 Semicarbazone
&&- 缩（对称）二氨基脲 Carbazone
&&- 氨基硫脲 Thiosemicarbazide
&&- 硫代卡巴肼 Thiocarbazide
&&- 缩氨基硫脲 Thiosemicarbazone
&&- 硫卡巴腙 Thiocarbazone
&&- 异氰酸酯 Isocyanate
&&- 氰酸酯 Cyanate
&&- 异硫氰酸酯 Isothiocyanate
&&- 硫氰酸酯 Thiocyanate
&&- 碳二亚胺 Carbodiimide
&&- 原碳酸衍生物 Orthocarbonic derivatives
- I.6 芳香族 Aromatics
&&- 酚 Phenol
&&- 邻二酚 1,2-Diphenol
&&- 芳基氯 Arylchloride
&&- 芳基氟 Arylfluoride
&&- 芳基溴 Arylbromide
&&- 芳基碘 Aryliodide
&&- 硫酚 Arylthiol
&&- 氮杂芳香环 Iminoarene
&&- 氧杂芳香环 Oxoarene
&&- 硫杂芳香环 Thioarene
&&- 芳环上有含氢碱性氮原子 Hetero N basic H
&&- 芳环上有不含氢碱性氮原子 Hetero N basic no H
&&- 芳环上有非碱性氮原子 Hetero N nonbasic
&&- 芳环上有氧原子 Hetero O
&&- 芳环上有硫原子 Hetero S
&&- 含杂原子芳香化合物 Heteroaromatic
Part II: 氮，硫，磷，硅，硼原子 N, S, P, Si, B
- II.1 氮 Nitrogen
&&- 亚硝酸盐 Nitrite
&&- 硫代亚硝酸盐 Thionitrite
&&- 硝酸盐 Nitrate
&&- 硝基 Nitro
&&- 亚硝基 Nitroso
&&- 叠氮化合物 Azide
&&- 酰叠氮 Acylazide
&&- 重氮基 Diazo
&&- 重氮盐 Diazonium
&&- 亚硝胺 Nitrosamine
&&- 亚硝酰胺 Nitrosamide
&&- 氧化胺 N-Oxide
&&- 肼 Hydrazine
&&- 腙 Hydrazone
&&- 羟胺 Hydroxylamine
- II.2 硫 Sulfur
&&- 砜 Sulfon
&&- 亚砜 Sulfoxide
&&- 锍盐 Sulfonium
&&- 硫酸 Sulfuric acid
&&- 硫酸单酯 Sulfuric monoester
&&- 硫酸二酯 Sulfuric diester
&&- 硫酸单酰胺 Sulfuric monoamide
&&- 硫酸双酰胺 Sulfuric diamide
&&- 硫酸单酰胺酯 Sulfuric esteramide
&&- 硫酸衍生物 Sulfuric derivative
&&- 磺酸 Sulfonic acid
&&- 磺酰胺 Sulfonamide
&&- 磺酸酯 Sulfonic ester
&&- 磺酰卤 Sulfonic halide
&&- 磺酸衍生物 Sulfonic derivative
&&- 亚磺酸 Sulfinic acid
&&- 亚磺酰胺 Sulfinic amide
&&- 亚磺酸酯 Sulfinic ester
&&- 亚磺酰卤 Sulfinic halide
&&- 亚磺酸衍生物 Sulfinic derivative
&&- 次磺酸 Sulfenic acid
&&- 次磺酰胺 Sulfenic amide
&&- 次磺酸酯 Sulfenic ester
&&- 次磺酰卤 Sulfenic halide
&&- 次磺酸衍生物 Sulfenic derivative
- II.3 磷 Phosphorous
&&- 膦 Phosphine
&&- 氧化膦 Phosphine oxide
&&- 鏻盐 Phosphonium
&&- 磷酰基 Phosphorylen
&&- 膦酸 Phosphonic acid
&&- 膦酸单酯 Phosphonic monoester
&&- 膦酸双酯 Phosphonic diester
&&- 膦酸单酰胺 Phosphonic monoamide
&&- 膦酸双酰胺 Phosphonic diamide
&&- 膦酸单酰胺酯 Phosphonic esteramide
&&- 膦酸衍生物 Phosphonic acid derivative
&&- 磷酸 Phosphoric acid
&&- 磷酸单酯 Phosphoric monoester
&&- 磷酸双酯 Phosphoric diester
&&- 磷酸三酯 Phosphoric triester
&&- 磷酸单酰胺 Phosphoric monoamide
&&- 磷酸双酰胺 Phosphoric diamide
&&- 磷酸三酰胺 Phosphoric triamide
&&- 膦酸单酯单酰胺 Phosphoric monoestermonoamide
&&- 膦酸双酯单酰胺 Phosphoric diestermonoamide
&&- 膦酸单酯双酰胺 Phosphoric monoesterdiamide
&&- 磷酸衍生物 Phosphoric acid derivative
&&- 次膦酸 Phosphinic acid
&&- 次膦酸酯 Phosphinic ester
&&- 次膦酸酰胺 Phosphinic amide
&&- 次膦酸 Phosphinic acid derivative
&&- 亚膦酸 Phosphonous acid
&&- 亚膦酸单酯 Phosphonous monoester
&&- 亚膦酸双酯 Phosphonous diester
&&- 亚膦酸单酰胺 Phosphonous monoamide
&&- 亚膦酸双酰胺 Phosphonous diamide
&&- 亚膦酸单酰胺酯 Phosphonous esteramide
&&- 亚膦酸衍生物 Phosphonous derivatives
&&- 三价膦酸 Phosphinous acid
&&- 三价膦酸酯 Phosphinous ester
&&- 三价膦酸酰胺 Phosphinous amide
&&- 三价膦酸衍生物 Phosphinous derivatives
- II.4 硅 Silicon
&&- 四取代硅烷（全取代） Quart silane
&&- 非四级硅烷（含氢原子） Non-quart silane
&&- 单卤代硅烷 Silylmonohalide
&&- 单杂三烷基硅烷 Het trialkylsilane
&&- 二杂二烷基硅烷 Dihet dialkylsilane
&&- 三杂单烷基硅烷 Trihet alkylsilane
&&- 硅酸衍生物 Silicic acid derivative
- II.5 硼 Boron
&&- 三烷基硼烷 Trialkylborane
&&- 硼酸衍生物 Boric acid derivatives
&&- 一烃基硼酸衍生物 Boronic acid derivative
&&- 硼氢化物 Borohydride
&&- 四取代硼原子 Quaternary boron
Part III: 特殊结构特征 Some Special Patterns
- III.1 链状结构 Chains
- III.2 环状结构 Rings
&&- 芳香环 Aromatic
&&- 杂环 Heterocyclic
&&- 环氧化合物 Epoxide
&&- 氮杂环丙烷 NH aziridine
&&- 螺环 Spiro
&&- 并环 Annelated rings
&&- 桥环 Bridged rings
- III.3 糖、核苷/核苷酸，甾族化合物 Sugars and Nucleosides/Nucleotides, Steroids
&&- 糖，含至少一个氧原子以及一个（五员环）或两个（六员环）氧取代基 Sugar pattern 1
&&- 糖，含至少一个氧原子以及2位上的缩醛键 Sugar pattern 2
&&- 糖，以上两种的并集 Sugar pattern combi
&&- 还原性糖（半缩醛） Sugar pattern 2 reducing
&&- 还原性糖（alpha构型） Sugar pattern 2 alpha
&&- 还原性糖（beta构型） Sugar pattern 2 beta
- III.4 其他结构特征 Everything else...
&&- 共轭双键 Conjugated double bond
&&- 共轭三键 Conjugated tripple bond
&&- 顺式双键 Cis double bond
&&- 反式双键 Trans double bond
&&- 混合酸酐 Mixed anhydrides
&&- 卤代杂原子 Halogen on hetero
&&- 卤素多取代 Halogen multi subst
&&- 三氟甲基 Trifluoromethyl
&&- 碳-氧、氮、硫键 C ONS bond
&&- 带电荷 Charged
&&- 阴离子 Anion
&&- 阳离子 Kation
&&- 盐 Salt
&&- 1,3互变异构 1,3-Tautomerizable
&&- 1,5互变异构 1,5-Tautomerizable
&&- 带自由旋转化学键 Rotatable bond
&&- Michael加成受体 Michael acceptor
&&- 偶氮二羧酸衍生物 Dicarbodiazene
&&- 酸性C-H CH-acidic
&&- 强酸性C-H CH-acidic strong
&&- 有手性中心 Chiral center specified
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2-(5-amino-1H-1,2,4-triazol-3-yl)benzoic acid
ChemBase编号：60279
分子式：C9H8N4O2
平均质量：204.18542
单一同位素质量：204.
SMILES和InChIs
n1c(n[nH]c1N)c1c(C(=O)O)cccc1
Canonical SMILES:
OC(=O)c1ccccc1c1n[nH]c(n1)N
InChI=1S/C9H8N4O2/c10-9-11-7(12-13-9)5-3-1-2-4-6(5)8(14)15/h1-4H,(H,14,15)(H3,10,11,12,13)
GSWHDMVMXOOKEU-UHFFFAOYSA-N
引用这个纪录
CBID:60279 /molecule-60279.html
名称和登记号
名称和登记号
名称 登记号
IUPAC标准名
2-(5-amino-1H-1,2,4-triazol-3-yl)benzoic acid
IUPAC传统名
2-(5-amino-1H-1,2,4-triazol-3-yl)benzoic acid
2-(5-Amino-1H-1,2,4-triazol-3-yl)benzoic acid
PubChem SID
PubChem CID
所有数据来源 商品来源 非商品来源
理论计算性质
理论计算性质
2.6640005&
LogD (pH = 5.5)
LogD (pH = 7.4)
-2.040467&
摩尔折射率
65.7605&cm3
20.030252&&A3
极化表面积
104.89&&Aring2
可自由旋转的化学键
里宾斯基五规则
生物活性(PubChem)
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