(1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide | 622840-45-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide
• 英文别名: (NE,S)-N-benzylidene-2-[(1R,2R,4R)-4-methyl-2-trimethylsilyloxycyclohexyl]propane-2-sulfinamide
• CAS: 622840-45-3
• 化学式: C₂₀H₃₃NO₂SSi
• 分子量: 379.639
• InChiKey: LHNBSESWNIEPEO-URGKXDFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide 在 hydrochloric acid diethyl ether 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-(+)-1-苯丙胺盐酸盐
  参考文献：
  名称：

  New, recoverable and highly effective sulfinyl chiral auxiliary

  摘要：

  A facile synthesis of a bicyclic 8-menthylsulfinate is described. The reaction of this sultine with organometallic compounds leads to gamma-hydroxysulfoxides, while the reaction with lithium amide affords 8-menthylsulfinamide. The chiral efficiency of the 8-menthylsulfinyl auxiliary was tested in the reaction of sulfinimines with Grignard reagents. A highly stereoselective addition of ethylmagnesium bromide to 8-menthylsulfinimine was observed (98% de). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00624-4
• 作为产物：
  描述：

  苯甲醛 、 (1R,2R,4R,S_S)-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以92%的产率得到(1R,2R,4R,S_S)-N-[(1E)-benzylidene]-2-(2-trimethylsilyloxy-4-methylcyclohexyl)propane-2-sulfinamide
  参考文献：
  名称：

  New, recoverable and highly effective sulfinyl chiral auxiliary

  摘要：

  A facile synthesis of a bicyclic 8-menthylsulfinate is described. The reaction of this sultine with organometallic compounds leads to gamma-hydroxysulfoxides, while the reaction with lithium amide affords 8-menthylsulfinamide. The chiral efficiency of the 8-menthylsulfinyl auxiliary was tested in the reaction of sulfinimines with Grignard reagents. A highly stereoselective addition of ethylmagnesium bromide to 8-menthylsulfinimine was observed (98% de). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00624-4

文献信息

• New, recoverable and highly effective sulfinyl chiral auxiliary
  作者：Robert Kawęcki

  DOI：10.1016/s0957-4166(03)00624-4

  日期：2003.9

  A facile synthesis of a bicyclic 8-menthylsulfinate is described. The reaction of this sultine with organometallic compounds leads to gamma-hydroxysulfoxides, while the reaction with lithium amide affords 8-menthylsulfinamide. The chiral efficiency of the 8-menthylsulfinyl auxiliary was tested in the reaction of sulfinimines with Grignard reagents. A highly stereoselective addition of ethylmagnesium bromide to 8-menthylsulfinimine was observed (98% de). (C) 2003 Elsevier Ltd. All rights reserved.