(+)-(8S,8aS,SR)-8-<(4-methylphenyl)sulfinyl>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone | 123642-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+)-(8S,8aS,SR)-8-<(4-methylphenyl)sulfinyl>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone
• 英文别名: (+)-(8S,8aS,SR)-8-[(4-methylphenyl)sulfinyl]-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone；(8S,8aS)-8-[(R)-(4-methylphenyl)sulfinyl]-2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 123642-82-0
• 化学式: C₁₅H₁₉NO₂S
• 分子量: 277.387
• InChiKey: BBQWWBVJGVCCRW-NJSLBKSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (+)-(8S,8aS,SR)-8-<(4-methylphenyl)sulfinyl>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone 在 W-2 Raney nickel 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以98%的产率得到5(1H)-中氮茚酮,六氢-,(R)-
  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 、 sodium cyanoborohydride 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 溶剂黄146 为溶剂， 反应 10.25h， 生成 (+)-(8S,8aS,SR)-8-<(4-methylphenyl)sulfinyl>-1,2,3,5,6,7,8,8a-octahydro-5-indolizinone
  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