(2S,S_S)-methyl-2-{[2-cyclohexylsulfinyl]-2-(N,N-dimethylthiocarbamoyl)ethyl}prop-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,S_S)-methyl-2-{[2-cyclohexylsulfinyl]-2-(N,N-dimethylthiocarbamoyl)ethyl}prop-2-enoate
• 英文别名: methyl (4S)-4-[(S)-cyclohexylsulfinyl]-5-(dimethylamino)-2-methylidene-5-sulfanylidenepentanoate
• 化学式: C₁₅H₂₅NO₃S₂
• 分子量: 331.5
• InChiKey: JZQMKRZGRQCXBG-ZSEKCTLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(溴甲基)丙烯酸甲酯 、 (R)-2-cyclohexylsulfinyl-N,N-dimethylethanethioamide 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.17h， 生成 (2R,S_R)-methyl-2-{[2-cyclohexylsulfinyl]-2-(N,N-dimethylthiocarbamoyl)ethyl}prop-2-enoate 、 (2S,S_R)-methyl-2-{[2-cyclohexylsulfinyl]-2-(N,N-dimethylthiocarbamoyl)ethyl}prop-2-enoate 、 (2R,S_S)-methyl-2-{[2-cyclohexylsulfinyl]-2-(N,N-dimethylthiocarbamoyl)ethyl}prop-2-enoate 、 (2S,S_S)-methyl-2-{[2-cyclohexylsulfinyl]-2-(N,N-dimethylthiocarbamoyl)ethyl}prop-2-enoate
  参考文献：
  名称：

  Highly Stereoselective C-Allylation of an Enantiopure α-Sulfinyl Thioacetamide

  摘要：

  The alkylation of the lithium enolate of enantiopure alpha-cyclohexylsulfinyl thioacetamide 1 with allyl bromides 5 possessing an electron-withdrawing group at the vinylic position does not occur at the sulfur center - as expected in the sulfur series - but at the carbon center through conjugate addition followed by bromide elimination. The modest to excellent 1,2-asymmetric induction achieved by the alkylsulfinyl group (dr up to 100:0) is explained by an electronic model.

  DOI：

  10.1021/jo0258610

文献信息

• Highly Stereoselective <i>C</i>-Allylation of an Enantiopure α-Sulfinyl Thioacetamide
  作者：Stéphanie Nowaczyk、Carole Alayrac、Patrick Metzner、Marie-Thérèse Averbuch-Pouchot

  DOI：10.1021/jo0258610

  日期：2002.9.1

  The alkylation of the lithium enolate of enantiopure alpha-cyclohexylsulfinyl thioacetamide 1 with allyl bromides 5 possessing an electron-withdrawing group at the vinylic position does not occur at the sulfur center - as expected in the sulfur series - but at the carbon center through conjugate addition followed by bromide elimination. The modest to excellent 1,2-asymmetric induction achieved by the alkylsulfinyl group (dr up to 100:0) is explained by an electronic model.