(5aS,8aR,SS)-1H-9-<(4-methylphenyl)sulfinyl>-2,3,5,5a,6,7,8,8a-octahydro-5-oxocyclopentindolizine | 123642-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5aS,8aR,SS)-1H-9-<(4-methylphenyl)sulfinyl>-2,3,5,5a,6,7,8,8a-octahydro-5-oxocyclopentindolizine
• 英文别名: (5aS,8aR)-9-[(S)-(4-methylphenyl)sulfinyl]-1,2,3,5a,6,7,8,8a-octahydrocyclopenta[f]indolizin-5-one
• CAS: 123642-83-1
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: BNLWQEZRYHGQMI-GTQRCTGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (5aS,8aR,SS)-1H-9-<(4-methylphenyl)sulfinyl>-2,3,5,5a,6,7,8,8a-octahydro-5-oxocyclopentindolizine 在 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以89%的产率得到(5aS,8aR,9S,9aS,SR)-1H-decahydro-9-<(4-methylphenyl)sulfinyl>-5-oxocyclopentindolizine
  参考文献：
  名称：

  Stereoselective additions of chiral .alpha.-sulfinyl ketimine anions to ene esters. Asymmetric syntheses of indolo[2,3-a]quinolizidine and yohimban alkaloids

  摘要：

  The in-situ 1,4-addition/ring-closure reactions of chiral alpha-sulfinyl ketimine anions with acyclic and cyclic ene esters offer a simple, convenient route for the construction of chiral cyclic alkaloids having a nitrogen-atom ring juncture. Asymmetric induction in the conjugate-addition reaction of the carbanions derived from alpha-sulfinyl ketimines possessing chiral sulfur with various cyclic and acyclic ene esters, subsequent ring-closure reaction, and reduction of the resulting beta-sulfinyl enamides were utilized in the syntheses of (-)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a] quinolizine [(-)-1], (-)-alloyohimban [(-)-2], (+)-3-epi-alloyohimban [(+)-3], and (-)-yohimban [(-)-4].

  DOI：

  10.1021/jo00025a011
• 作为产物：
  描述：

  2-甲基吡咯啉 在 正丁基锂 、 lithium diisopropyl amide 作用下， 反应 6.25h， 生成 (5aS,8aR,SS)-1H-9-<(4-methylphenyl)sulfinyl>-2,3,5,5a,6,7,8,8a-octahydro-5-oxocyclopentindolizine
  参考文献：
  名称：

  Stereoselective addition reactions of chiral .alpha.-sulfinyl ketimine anions with ene esters. Facile asymmetric synthesis of indolo[2,3-a]quinolizidine and yohimbanoid alkaloids

  摘要：

  DOI：

  10.1021/jo00285a009

文献信息

• HUA, DUY H.;BHARATHI, S. NARASIMHA;TAKUSAGAWA, FUSAO;TSUJIMOTO, ATSUKO;PA+, J. ORG. CHEM., 54,(1989) N4, C. 5659-5662
  作者：HUA, DUY H.、BHARATHI, S. NARASIMHA、TAKUSAGAWA, FUSAO、TSUJIMOTO, ATSUKO、PA+

  DOI：——

  日期：——