(-)menthyl 3(R)-(N-benzylamino)-2(R)-(-)-menthoxycarbonyl-1(R)-cyclohexane-1-acetate | 143169-29-3

• 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: (-)menthyl 3(R)-(N-benzylamino)-2(R)-(-)-menthoxycarbonyl-1(R)-cyclohexane-1-acetate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (1R,2R,6R)-2-(benzylamino)-6-[2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-2-oxoethyl]cyclohexane-1-carboxylate
• CAS: 143169-29-3
• 化学式: C₃₆H₅₇NO₄
• 分子量: 567.853
• InChiKey: KUQLKXWXEPYSHU-JRYKXTTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  lithium N-benzyltrimethylsilylamide 、 Di-(-)menthyl nona-2,7-diene-1,9-dioate 以 乙醚 为溶剂， 生成 (-)menthyl 3(R)-(N-benzylamino)-2(R)-(-)-menthoxycarbonyl-1(R)-cyclohexane-1-acetate 、 (-)menthyl 3(S)-(N-benzylamino)-2(S)-(-)-menthoxycarbonyl-1(S)-cyclohexane-1-acetate
  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.