2-[(3R,3aR,5aS,6S,7S,9aR,9bS)-3a,6-dimethyl-3-[(2R)-6-methylheptan-2-yl]-6-(2-oxoethyl)-2,3,4,5,5a,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl]acetaldehyde | 884195-40-8

• 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: 2-[(3R,3aR,5aS,6S,7S,9aR,9bS)-3a,6-dimethyl-3-[(2R)-6-methylheptan-2-yl]-6-(2-oxoethyl)-2,3,4,5,5a,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl]acetaldehyde
• CAS: 884195-40-8
• 化学式: C₂₇H₄₆O₂
• 分子量: 402.661
• InChiKey: CBZVGUIXOLZMAX-CJPSHIORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(3R,3aR,5aS,6S,7S,9aR,9bS)-3a,6-dimethyl-3-[(2R)-6-methylheptan-2-yl]-6-(2-oxoethyl)-2,3,4,5,5a,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl]acetaldehyde 在 (S)-吲哚啉-2-羧酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.0h， 以47%的产率得到(3aS,3bS,5aR,6R,8aS,8bS,10aS)-3a,5a-dimethyl-6-[(2R)-6-methylheptan-2-yl]-1,3b,4,5,6,7,8,8a,8b,9,10,10a-dodecahydroindeno[6,7-e]indene-3-carbaldehyde
  参考文献：
  名称：

  Regioselective aldol condensations of a cholestanone-derived dialdehyde: new twists on a classic reaction

  摘要：

  Methods have been developed for the regioselective formation of both aldol condensation products from a non-symmetrical dialdehyde derived from 5 alpha-cholestan-3-one. The findings disclosed herein, as well as their mechanistic implications, should assist in achieving selective intramolecular aldol closures in other contexts. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.136
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 sodium tetrahydroborate 、 sodium periodate 、 silica gel 、 溶剂黄146 、 亚硝基苯 、 L-脯氨酸 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.34h， 生成 2-[(3R,3aR,5aS,6S,7S,9aR,9bS)-3a,6-dimethyl-3-[(2R)-6-methylheptan-2-yl]-6-(2-oxoethyl)-2,3,4,5,5a,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl]acetaldehyde
  参考文献：
  名称：

  Regioselective aldol condensations of a cholestanone-derived dialdehyde: new twists on a classic reaction

  摘要：

  Methods have been developed for the regioselective formation of both aldol condensation products from a non-symmetrical dialdehyde derived from 5 alpha-cholestan-3-one. The findings disclosed herein, as well as their mechanistic implications, should assist in achieving selective intramolecular aldol closures in other contexts. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.136

文献信息

• Regioselective aldol condensations of a cholestanone-derived dialdehyde: new twists on a classic reaction
  作者：Scott A. Snyder、E.J. Corey

  DOI：10.1016/j.tetlet.2006.01.136

  日期：2006.3

  Methods have been developed for the regioselective formation of both aldol condensation products from a non-symmetrical dialdehyde derived from 5 alpha-cholestan-3-one. The findings disclosed herein, as well as their mechanistic implications, should assist in achieving selective intramolecular aldol closures in other contexts. (c) 2006 Elsevier Ltd. All rights reserved.