2-methylthio-1-o-tolyl-1H-imidazole | 116072-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methylthio-1-o-tolyl-1H-imidazole
• 英文别名: 1-(2-Methylphenyl)-2-methylsulfanylimidazole
• CAS: 116072-39-0
• 化学式: C₁₁H₁₂N₂S
• 分子量: 204.296
• InChiKey: XOBMNVOVYLQXAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻甲苯异硫氰酸酯 在 sodium hydroxide 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 2.0h， 生成 2-methylthio-1-o-tolyl-1H-imidazole
  参考文献：
  名称：

  Catalytic asymmetric oxidation of sulfide with titanium–mandelic acid complex: practical synthesis of (S)-3-[1-(2-methylphenyl)imidazol-2-ylsulfinyl]propan-1-ol, the key intermediate of OPC-29030

  摘要：

  An effective catalytic asymmetric oxidation of prochiral sulfide 1a to (S)-2a has been achieved by the use of chiral titaniummandelic acid complex. The enantioselectivity was found to be not influenced by moisture, and moderate to high selectivity (76% ee) was obtained at room temperature (25 degreesC). Thus a practical synthetic method for the platelet adhesion inhibitor, OPC-29030, was established utilising asymmetric oxidation of 1a. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00152-1

文献信息

• Reaction of Dimethyl<i>N</i>-Aryl- and<i>N</i>-Alkylcarbonimidodithioates with Aminoacetaldehyde Diethyl Acetal: A Direct Synthesis of 1-Aryl- and 1-Alkyl-2-methylthioimidazoles
  作者：Dinah Pooranchand、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa

  DOI：10.1055/s-1987-28201

  日期：——

  The reaction of dimethyl N-aryl- or N-alkylcarbonimidodithioates with aminoacetaldehyde diethyl acetal in refluxing acetic acid affords 1-aryl or 1-alkyl-2-methylthioimidazoles in good yields. Dimethyl N-isopropylcarbonimidodithioate gave 1-isopropylimidazole-2(3H)-thione under similar conditions.

  N-芳基或 N-烷基二硫代碳亚氨基甲酸酯二甲酯与氨基乙醛缩二乙醇在回流乙酸中反应，可以得到 1-芳基或 1-烷基-2-甲硫基咪唑，收率很高。在类似条件下，N-异丙基二硫代碳酰亚胺二甲酯可生成 1-异丙基咪唑-2(3H)-硫酮。
• POORANCHAND, DINAH;ILA, HIRIYAKKANAVAR;JUNJAPPA, HIRIYAKKANAVAR, SYNTHESIS,(1987) N 12, 1136-1138
  作者：POORANCHAND, DINAH、ILA, HIRIYAKKANAVAR、JUNJAPPA, HIRIYAKKANAVAR

  DOI：——

  日期：——
• Catalytic asymmetric oxidation of sulfide with titanium–mandelic acid complex: practical synthesis of (S)-3-[1-(2-methylphenyl)imidazol-2-ylsulfinyl]propan-1-ol, the key intermediate of OPC-29030
  作者：Masato Matsugi、Norio Fukuda、Yasuaki Muguruma、Taizo Yamaguchi、Jun-ichi Minamikawa、Sei Otsuka

  DOI：10.1016/s0040-4020(01)00152-1

  日期：2001.4

  An effective catalytic asymmetric oxidation of prochiral sulfide 1a to (S)-2a has been achieved by the use of chiral titaniummandelic acid complex. The enantioselectivity was found to be not influenced by moisture, and moderate to high selectivity (76% ee) was obtained at room temperature (25 degreesC). Thus a practical synthetic method for the platelet adhesion inhibitor, OPC-29030, was established utilising asymmetric oxidation of 1a. (C) 2001 Elsevier Science Ltd. All rights reserved.