(S)-2-methyl-N-(thiophen-2-ylmethyl)propane-2-sulfinamide | 1451069-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (S)-2-methyl-N-(thiophen-2-ylmethyl)propane-2-sulfinamide
• CAS: 1451069-33-2
• 化学式: C₉H₁₅NOS₂
• 分子量: 217.356
• InChiKey: HVBQYPMBCSGUIW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2-methyl-N-(thiophen-2-ylmethylene)propane-2-sulfinamide 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.5h， 以95%的产率得到(S)-2-methyl-N-(thiophen-2-ylmethyl)propane-2-sulfinamide
  参考文献：
  名称：

  2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc

  摘要：

  Chiral 2-pyridylsulfinamides were shown to be effective catalysts in the alkylation of aryl and alkyl aldehydes with diethylzinc providing the corresponding alcohols in excellent enantioselectivity. Sulfinamide catalysts possessing solitary chirality at the sulfur center produced the product phenethyl alcohol in good enantioselectivity. Diastereomeric sulfinamides possessing chirality at the carbon-bearing nitrogen and at the sulfur of the sulfinamide increased the enantioselectivity of the product alcohols up to >99%. However, there is no effect of the match-mismatch pair of sulfinamide diastereomers on the outcome of the chiral induction of the product phenethyl alcohols. It was conclusively proved that chirality at the sulfur center is mandatory for obtaining good enantioselectivity in the reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.061