[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3S)-3-(benzylamino)decanoate | 143121-62-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3S)-3-(benzylamino)decanoate
• CAS: 143121-62-4
• 化学式: C₂₇H₄₅NO₂
• 分子量: 415.66
• InChiKey: GPDSSNKDGJTRTQ-HMNRDNJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  lithium N-benzyltrimethylsilylamide 、 (E)-2-decenoic acid menthyl ester 在 copper(l) iodide 、 zinc(II) chloride 作用下， 生成 [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3S)-3-(benzylamino)decanoate 、 [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3R)-3-(benzylamino)decanoate
  参考文献：
  名称：

  Asymmetric cyclization via tandem conjugate addition by using metal amide reagents. Importance of the folded orientation of two enoate moieties

  摘要：

  Di-(-)-menthylnona-2,7-diene-1,9-dioate (1) is converted to (-)-menthyl 3(S)-(N-benzylamino)-2(S)-(-)-menthoxycarbonyl)-1(S)-cyclohexane-1-acetate (2) with high diastereoselectivity upon treatment with the amide cuprate or zincate reagent Bn(TMS)NML(n) in the presence of ZnCl2. The folded orientation of the two enoate moieties in 1 is essential for this high asymmetric cyclization via tandem conjugate addition.

  DOI：

  10.1021/jo00045a003

文献信息

• Asymmetric cyclization via tandem conjugate addition by using metal amide reagents. Importance of the folded orientation of two enoate moieties
  作者：Naomi Shida、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1021/jo00045a003

  日期：1992.9

  Di-(-)-menthylnona-2,7-diene-1,9-dioate (1) is converted to (-)-menthyl 3(S)-(N-benzylamino)-2(S)-(-)-menthoxycarbonyl)-1(S)-cyclohexane-1-acetate (2) with high diastereoselectivity upon treatment with the amide cuprate or zincate reagent Bn(TMS)NML(n) in the presence of ZnCl2. The folded orientation of the two enoate moieties in 1 is essential for this high asymmetric cyclization via tandem conjugate addition.