4-丙烯基-5-(2-甲氧基苯基)-4H-1,2,4-噻唑-3-硫醇 | 23195-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-丙烯基-5-(2-甲氧基苯基)-4H-1,2,4-噻唑-3-硫醇
• 中文别名: 4-烯丙基-5-(2-甲氧苯基)-2H-1,2,4-三唑-3-硫酮；5-(2-甲氧苯基)-4-丙-2-烯基-2H-1,2,4-三唑-3-硫酮；4-烯丙基-5-(2-甲氧苯基)-4H-1,2,4-三唑-3-硫醇
• 英文名称: 3-(2'-methoxyphenyl)-4-allyl-5-mercapto-1,2,4-triazole
• 英文别名: 3-(o-Methoxy-phenyl)-4-allyl-5-mercapto-4H-1,2,4-triazol；4-allyl-5-(2-methoxy-phenyl)-2,4-dihydro-[1,2,4]triazole-3-thione；4-allyl-5-(2-methoxyphenyl)-4H-1,2,4-triazole-3-thiol；3-(2-methoxyphenyl)-4-prop-2-enyl-1H-1,2,4-triazole-5-thione
• CAS: 23195-30-4
• 化学式: C₁₂H₁₃N₃OS
• mdl: MFCD01959323
• 分子量: 247.321
• InChiKey: DPRJSPFDWWPZKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-丙烯基-5-(2-甲氧基苯基)-4H-1,2,4-噻唑-3-硫醇 在 溴 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 3-(2-methoxyphenyl)-6-methyl[1,3]thiazolo-[2,3-c][1,2,4]triazole
  参考文献：
  名称：

  Synthesis and properties of thiazolo[2,3-c][1,2,4]triazoles

  摘要：

  Effects of different factors on the electrophilic halocyclization of 3-substituted 4-allyl(or 2-methylprop-2-en-1-yl)-1,2,4-triazole-5(1H)-thiones were studied. The only reaction products were thiazolo[2,3-c]-[1,2,4]triazoles. Some their transformations afforded new derivatives that can find application in pharmacology.

  DOI：

  10.1134/s1070428015100206

文献信息

• Alkylation of 1,2,4-triazole-3-thiols with haloalkanoic acid esters
  作者：M. A. Samvelyan、T. V. Ghochikyan、S. V. Grigoryan、R. A. Tamazyan、A. G. Aivazyan

  DOI：10.1134/s1070428017060203

  日期：2017.6

  Alkylation of 4,5-disubstituted 4H-1,2,4-triazole-3-thiols with methyl chloroformate and ethyl chloroacetate chemoselectively afforded the corresponding S-alkyl derivatives, whereas the alkylation of 5-benzyl-4-phenyl-4H-1,2,4-triazole-3-thiol with methyl 3-bromopropanoate gave an inseparable mixture of S- and N-alkylation products. Hydrazinolysis of S-(5-benzyl-4-phenyl-4H-1,2,4-triazol-3-yl) methyl

  4,5-二取代的4 H -1,2,4-三唑-3-硫醇与氯甲酸甲酯和氯乙酸乙酯的烷基化反应产生相应的S-烷基衍生物，而5-苄基-4-苯基-4 H的烷基化-1,2,4-三唑-3-硫醇与3-溴丙酸甲酯形成不可分离的S-和N-烷基化产物混合物。的肼解小号- （5-苄基-4-苯基-4- ħ -1,2,4-三唑-3-基）甲基碳酸酯所涉及的异常裂解与形成的初始4,5-二取代的1,2,4-三唑的和肼甲酸甲酯。
• Asymmetric synthesis of β-heterocycle substituted l-α-amino acids
  作者：A.S. Saghiyan、A.V. Geolchanyan、S.G. Petrosyan、T.V. Ghochikyan、V.S. Haroutunyan、A.A. Avetisyan、Yu.N. Belokon’、K. Fisher

  DOI：10.1016/j.tetasy.2003.12.007

  日期：2004.2

  A new efficient method of asymmetric synthesis of β-heterocycle substituted l-α-amino acids through the addition of 3-amino-1,2,4-thiodiazole and 5-mercapto-1,2,4-triazoles, containing various substituents at the 3 and 4 positions, to the CC bond of dehydroalanine in the Ni(II) complex of its Schiff base with (S)-2-N-(N′-benzylprolyl)aminobenzophenone has been elaborated upon. Under thermodynamic

  通过添加3-氨基-1,2,4-硫代二唑和5-巯基-1,2,4-三唑的不对称合成β-杂环取代的1-α-氨基酸的新有效方法在3个4位，以脱氢丙氨酸的在镍（II）络合物及其席夫碱与（的CC键小号）-2- ñ - （ñ ' -benzylprolyl）氨基二苯甲酮已被详细阐述。在热力学控制下，亲核加成的立体选择性超过94％。将反应混合物酸分解后，分离出具有高对映体纯度（ee> 98.5％）的相应β-杂环取代的α-氨基酸。
• Asymmetric synthesis of (R)-S-(1,2,4-triazol-3-yl)cysteines by nucleophilic addition of triazolethiols to a Ni^IIcomplex with a chiral dehydroalanine Schiff base
  作者：A. S. Saghiyan、A. V. Geolchanyan、L. L. Manasyan、G. M. Mkrtchyan、N. R. Martirosyan、S. A. Dadayan、T. V. Kochickyan、V. S. Harutyunyan、A. A. Avetisyan、V. I. Tararov、V. I. Maleev、Yu. N. Belokon"

  DOI：10.1023/b:rucb.0000037866.13065.c7

  日期：2004.4

  An efficient method was developed for the asymmetric synthesis of (R)-S-(1,2,4-triazol-3yl)cysteines by the addition of 3,4-disubstituted 1,2,4-triazole-5-thiols at the electrophilic C=C bond in a Ni-II complex of a Schiff base of dehydroalanine with (S)-N-(N-benzylprolyl)aminobenzophenone. The stereoselectivity of the formation of diastereomeric complexes with the (S,R) configuration under conditions of thermodynamic control of the nucleophilic addition exceeds 94%. Acid treatment of the reaction mixtures afforded enantiomerically pure (R)-S-hetarylcysteines (ee > 98%).
• Synthesis and properties of thiazolo[2,3-c][1,2,4]triazoles
  作者：T. V. Kochikyan、M. A. Samvelyan、A. M. Petrosyan、P. D. Langer

  DOI：10.1134/s1070428015100206

  日期：2015.10

  Effects of different factors on the electrophilic halocyclization of 3-substituted 4-allyl(or 2-methylprop-2-en-1-yl)-1,2,4-triazole-5(1H)-thiones were studied. The only reaction products were thiazolo[2,3-c]-[1,2,4]triazoles. Some their transformations afforded new derivatives that can find application in pharmacology.