1-methyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester | 73500-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
• 英文别名: methyl 1-methyl-1,2,3-triazolo-4,5-dicarboxylate；dimethyl N(1)-methyl-4,5-carboxy-1,2,3-triazole；1-methyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester；1-Methyl-1H-[1,2,3]triazol-4,5-dicarbonsaeure-dimethylester；Dimethyl 1-methyl-1H-1,2,3-triazole-4,5-dicarboxylate；dimethyl 1-methyltriazole-4,5-dicarboxylate
• CAS: 73500-07-9
• 化学式: C₇H₉N₃O₄
• mdl: MFCD00465927
• 分子量: 199.166
• InChiKey: GNVGANLYVPXSIX-UHFFFAOYSA-N

物化性质

• 熔点：
  60-62 °C
• 沸点：
  289.1±43.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-methyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester 在 盐酸 、 一水合肼 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 39.0h， 生成 1-methyl-4-hydroxy-7-hydrazino-1,2,3-triazolo[4,5-d]pyridazine
  参考文献：
  名称：

  Barili, Pier Luigi, Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 889 - 894

  摘要：

  DOI：
• 作为产物：
  描述：

  1-trimethylsilanylmethyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99%的产率得到1-methyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  甲硅烷基官能化烷基叠氮化物，三甲基甲硅烷基甲基叠氮化物；乙炔双极性分子的合成和环负载反应

  摘要：

  热稳定的三甲基甲硅烷基甲基叠氮化物首先由氯甲基三甲基硅烷与叠氮化钠反应合成。在与炔属偶极亲和试剂的反应以及随后在氟离子存在下环加合物与醛和水的反应中，证明了其作为 α-官能化合成叠氮化物等价物的用途。

  DOI：

  10.1246/cl.1983.1131

文献信息

• PDE10 MODULATORS
  申请人：Bachmann Stephan

  公开号：US20130059833A1

  公开（公告）日：2013-03-07

  The present invention relates to compounds of formula (I) wherein R 1 , R 2 , R 3 , R 5 , W, X, X 1 , Y, Y 1 , Z and Z 1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used in the treatment of CNS disorders such as schizophrenia, Alzheimer's disease, and Parkinson's disease.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R5、W、X、X1、Y、Y1、Z和Z1如描述和权利要求中定义，并且其生理上可接受的盐。这些化合物抑制PDE10A，可用于治疗中枢神经系统疾病，如精神分裂症、阿尔茨海默病和帕金森病。
• [EN] PDE10 MODULATORS<br/>[FR] MODULATEURS DE PDE10
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013034506A1

  公开（公告）日：2013-03-14

  The present invention relates to compounds of formula (I) wherein R1, R2, R3, R5, W, X, X1, Y, Y1, Z and Z1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used as medicaments.

  本发明涉及以下式（I）的化合物，其中R1、R2、R3、R5、W、X、X1、Y、Y1、Z和Z1如描述和权利要求中所定义，并且其生理学上可接受的盐。这些化合物抑制PDE10A，可用作药物。
• Protecting-Group-Free Site-Selective Reactions in a Metal–Organic Framework Reaction Vessel
  作者：Michael. T. Huxley、Alexandre Burgun、Hanieh Ghodrati、Campbell J. Coghlan、Anthony Lemieux、Neil R. Champness、David M. Huang、Christian J. Doonan、Christopher J. Sumby

  DOI：10.1021/jacs.8b02896

  日期：2018.5.23

  bis-triazole side-product. Stepwise insights into conversions of the MOF reaction vessel were obtained by X-ray crystallography, demonstrating that the reactive sites are "isolated" from one another. Single-crystal to single-crystal transformations of the Mn(I)-metalated material 1·[Mn(CO)3(H2O)]Br to the corresponding azide species 1·[Mn(CO)3N3] with sodium azide, followed by a series of [3+2] azide-alkyne

  复杂分子的合成通常需要位点选择性有机转化。通过采用定制的金属有机骨架（MOF，1·[Mn(CO)3N3]），其中配位的叠氮化物阴离子精确定位在一维通道内，我们提出了一种将二炔转化为炔官能化的策略三唑类。作为这种方法的说明，1,7-octadiyne-3,6-dione 化学计量地提供单“点击”产物 N-methyl-4-hex-5'-ynl-1',4'-dione-1， 2,3-三唑，只有微量的双三唑副产物。通过 X 射线晶体学获得对 MOF 反应容器转化的逐步洞察，证明反应位点彼此“隔离”。Mn(I) 金属化材料 1·[Mn(CO)3(H2O)]Br 与叠氮化钠的单晶到单晶转变为相应的叠氮化物 1·[Mn(CO)3N3]，然后是报道了一系列 [3+2] 叠氮化物-炔烃环加成反应。“点击”产物从多孔材料中的最终释放是通过用 MeBr 进行 N-烷基化来实现的，其再生起始 MOF 1·[Mn(CO)3( )]Br
• Chemical compounds
  申请人：Ehrenfreund Josef

  公开号：US20060154967A1

  公开（公告）日：2006-07-13

  A compound of formula (I):, where A is an ortho-substituted ring selected from a number of specified rings; R 1 is halogen, cyano, nitro, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or C 1-4 haloalkoxy or optionally substituted C 2-4 alkenyl, optionally substituted C 2-4 alkynyl or optionally substituted SO2(C 1-4 alkyl) (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen and C 1-4 alkoxy); R 2 is C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy(C 1-4 )alkyl or C 1-4 alkylthio(C 1-4 )alkyl or [optionally substituted aryl](C 1-4 )alkyl- or [optionally substituted aryl]oxy(C 1-4 )alkyl (where the optionally substituted aryl moieties may each have up to 3 substituents, each independently selected from halogen and C 1-4 alkoxy); R 3 is hydrogen, CH 2 C≡CR 4 , CH 2 CR 4 ═C(H)R 4 , CH═C═CH 2 or COR 5 or optionally substituted C 1-4 alkyl, optionally substituted C 1-4 alkoxy or optionally substituted (C 1-4 )alkylC(═O)O (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen and C 1-4 alkoxy, C 1-4 alkyl, C 1-2 haloalkoxy, hydroxy, cyano, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl and ethylsulfonyl); each R 4 is, independently, hydrogen, halogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or C 1-4 alkoxy(C 1-4 )alkyl; and R 5 is hydrogen or optionally substituted C 1-6 alkyl, optionally substituted C 1-4 alkoxy, optionally substituted C 1-4 alkoxy(C 1-4 )alkyl, optionally substituted C 1-4 alkylthio(C 1-4 )alkyl or optionally substituted aryl (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen, C 1-6 alkoxy, C 1-6 haloalkoxy, cyano, hydroxy, methoxycarbonyl and ethoxycarbonyl).

  化合物的化学式为（I）：其中A是从指定环中选择的邻位取代环；R1是卤素，氰基，硝基，C1-4烷基，C1-4卤代烷基，C1-4烷氧基或C1-4卤代烷氧基，或者是可选取代的C2-4烯基，可选取代的C2-4炔基或可选取代的SO2（C1-4烷基）（其中可选取代基团可以各自具有多达3个取代基，每个取代基独立选择自卤素和C1-4烷氧基）；R2是C1-4烷基，C1-4卤代烷基，C1-4烷氧基（C1-4）烷基或C1-4烷硫基（C1-4）烷基，或[可选取代芳基]（C1-4）烷基-或[可选取代芳基]氧基（C1-4）烷基（其中可选取代基团可以各自具有多达3个取代基，每个取代基独立选择自卤素和C1-4烷氧基）；R3是氢， C≡CR4， CR4═C（H）R4，CH═C═CH2或COR5，或者是可选取代的C1-4烷基，可选取代的C1-4烷氧基或可选取代的（C1-4）烷基C（═O）O（其中可选取代基团可以各自具有多达3个取代基，每个取代基独立选择自卤素和C1-4烷氧基，C1-4烷基，C1-2卤代烷氧基，羟基，氰基，羧基，甲氧羰基，乙氧羰基，甲基磺酰基和乙基磺酰基）；每个R4独立地是氢，卤素，C1-4烷基，C1-4卤代烷基，C1-4烷氧基或C1-4烷氧基（C1-4）烷基；R5是氢或可选取代的C1-6烷基，可选取代的C1-4烷氧基，可选取代的C1-4烷氧基（C1-4）烷基，可选取代的C1-4烷硫基（C1-4）烷基或可选取代的芳基（其中可选取代基团可以各自具有多达3个取代基，每个取代基独立选择自卤素，C1-6烷氧基，C1-6卤代烷氧基，氰基，羟基，甲氧羰基和乙氧羰基）。
• MICROBIOCIDAL (E.G. FUNGICIDAL) 1,2,3-TRIAZOLE DERIVATIVES
  申请人：Ehrenfreund Josef

  公开号：US20090216027A1

  公开（公告）日：2009-08-27

  A compound of formula (I): where A is an ortho-substituted ring selected from a number of specified rings; R 1 is halogen, cyano, nitro, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or C 1-4 haloalkoxy or optionally substituted C 2-4 alkenyl, optionally substituted C 2-4 alkynyl or optionally substituted SO 2 (C 1-4 )alkyl (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen and C 1-4 alkoxy); R 2 is C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy(C 1-4 )alkyl or C 1-4 alkylthio(C 1-4 )alkyl or [optionally substituted aryl](C 1-4 )alkyl- or [optionally substituted aryl]oxy(C 1-4 )alkyl-(where the optionally substituted aryl moieties may each have up to 3 substituents, each independently selected from halogen and C 1-4 alkoxy); R 3 is hydrogen, CH 2 C≡CR 4 , CH 2 CR 4 ═C(H)R 4 , CH═C═CH 2 or COR 5 or optionally substituted C 1-4 alkyl, optionally substituted C 1-4 alkoxy or optionally substituted (C 1-4 ) alkylC(═O)O (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen and C 1-4 alkoxy, C 1-4 alkyl, C 1-2 haloalkoxy, hydroxy, cyano, carboxyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl and ethylsulfonyl); each R 4 is, independently, hydrogen, halogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or C 1-4 alkoxy(C 1-4 )alkyl; and R 5 is hydrogen or optionally substituted C 1-6 alkyl, optionally substituted C 1-4 alkoxy, optionally substituted C 1-4 alkoxy(C 1-4 )alkyl, optionally substituted C 1-4 alkylthio(C 1-4 )alkyl or optionally substituted aryl (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen, C 1-6 alkoxy, C 1-6 haloalkoxy, cyano, hydroxy, methoxycarbonyl and ethoxycarbonyl).

  化合物的化学式为(I):其中A是从指定环中选择的邻位取代环；R1是卤素、氰基、硝基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基或C1-4卤代烷氧基，或选择性取代的C2-4烯基、选择性取代的C2-4炔基或选择性取代的SO2(C1-4)烷基（其中选择性取代基团可以各自具有最多3个取代基，每个取代基可以独立选择卤素和C1-4烷氧基）；R2是C1-4烷基、C1-4卤代烷基、C1-4烷氧基(C1-4)烷基或C1-4烷硫基(C1-4)烷基或[选择性取代的芳基](C1-4)烷基-或[选择性取代的芳基]氧基(C1-4)烷基-（其中选择性取代的芳基基团可以各自具有最多3个取代基，每个取代基可以独立选择卤素和C1-4烷氧基）；R3是氢、 C≡CR4、 CR4═C(H)R4、CH═C═CH2或COR5或选择性取代的C1-4烷基、选择性取代的C1-4烷氧基或选择性取代的(C1-4)烷基C(═O)O（其中选择性取代基团可以各自具有最多3个取代基，每个取代基可以独立选择卤素和C1-4烷氧基、C1-4烷基、C1-2卤代烷氧基、羟基、氰基、羧基、甲氧基羰基、乙氧基羰基、甲基磺酰基和乙基磺酰基）；每个R4独立地是氢、卤素、C1-4烷基、C1-4卤代烷基、C1-4烷氧基或C1-4烷氧基(C1-4)烷基；而R5是氢或选择性取代的C1-6烷基、选择性取代的C1-4烷氧基、选择性取代的C1-4烷氧基(C1-4)烷基、选择性取代的C1-4烷硫基(C1-4)烷基或选择性取代的芳基（其中选择性取代基团可以各自具有最多3个取代基，每个取代基可以独立选择卤素、C1-6烷氧基、C1-6卤代烷氧基、氰基、羟基、甲氧基羰基和乙氧基羰基）。