methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate | 1338468-32-8

• 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: methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate
• CAS: 1338468-32-8
• 化学式: C₂₀H₃₃NO₅
• 分子量: 367.486
• InChiKey: VGDIIHWHENGGFK-UZLBHIALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  环庚烯 在 (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate 、 pyrrolidine propionic acid salt 、 碳酸氢钠 、 臭氧 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 3.0h， 生成 methyl rac-5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate 、 methyl 5-((1'S,2'R)-2-(ethyl(tert-butoxycarbonyl)amino)-1'-formylcyclohex-3'-enyl)pentanoate
  参考文献：
  名称：

  The enantioselective synthesis of tetracyclic methyllycaconitine analogues

  摘要：

  A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels-Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.026

文献信息

• The enantioselective synthesis of tetracyclic methyllycaconitine analogues
  作者：Kevin Sparrow、David Barker、Margaret A. Brimble

  DOI：10.1016/j.tet.2011.08.026

  日期：2011.10

  A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels-Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee. (C) 2011 Elsevier Ltd. All rights reserved.