methyl 3-oxo-(3'S)-(chloromethyl)-(4'R)-(nitromethyl)spiro[(2(1')R)-cyclopentane]-dihydrobetulonate | 1353990-81-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl 3-oxo-(3'S)-(chloromethyl)-(4'R)-(nitromethyl)spiro[(2(1')R)-cyclopentane]-dihydrobetulonate
• 英文别名: methyl (1S,3'S,3aS,4'R,5aR,5bR,7aR,10R,11aR,11bR,13aR,13bR)-3'-(chloromethyl)-5a,5b,8,8,11a-pentamethyl-4'-(nitromethyl)-9-oxo-1-propan-2-ylspiro[1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-10,1'-cyclopentane]-3a-carboxylate
• CAS: 1353990-81-4
• 化学式: C₃₇H₅₈ClNO₅
• 分子量: 632.324
• InChiKey: ZUTCIFUGNDGJCN-SUEPLCHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  44
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (1S,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-propan-2-yl-10,10-bis(prop-2-enyl)-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylate 在 Iron(III) nitrate nonahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以0.04 g的产率得到methyl 3-oxo-(3'S)-(chloromethyl)-(4'R)-(nitromethyl)spiro[(2(1')R)-cyclopentane]-dihydrobetulonate
  参考文献：
  名称：

  The first synthesis of spirocyclopentyl derivatives of lupane triterpenoids by radical nitrocyclization of C-2-diallyl substituted betulonates

  摘要：

  Radical cyclization of the 1,6-hexadiene moiety in 2,2-diallyl substituted methyl or benzyl dihydrobetulonates initiated by Fe(NO3)(3)center dot 9H(2)O in the presence of FeCl3 or LiCl gave hitherto unknown spirocyclic compounds in which ring A of the lupane triterpenoid at position C-2 is spiro coupled with a vicinally substituted nitromethyl- and chloromethylcyclopentane. Based on a quantum-chemical assessment of the energy characteristics of this reaction, the most probable configurations of the chiral atoms in the spirocyclopentane ring were determined for the major diastereomers isolated in individual form. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.020