(5aR,9aR,SS)-1,2,3,5,5a,6,7,8,9,9a-decahydro-10-<(4-methylphenyl)sulfinyl>-5-oxopyrrolo<1,2-b>isoquinoline | 137119-56-3

• 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: (5aR,9aR,SS)-1,2,3,5,5a,6,7,8,9,9a-decahydro-10-<(4-methylphenyl)sulfinyl>-5-oxopyrrolo<1,2-b>isoquinoline
• 英文别名: (5aR,9aR)-10-[(S)-(4-methylphenyl)sulfinyl]-2,3,5a,6,7,8,9,9a-octahydro-1H-pyrrolo[1,2-b]isoquinolin-5-one
• CAS: 137119-56-3
• 化学式: C₁₉H₂₃NO₂S
• 分子量: 329.463
• InChiKey: RBCGSHHGNYHTNH-LNPFQXMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• 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：

  (5aR,9aR,SS)-1,2,3,5,5a,6,7,8,9,9a-decahydro-10-<(4-methylphenyl)sulfinyl>-5-oxopyrrolo<1,2-b>isoquinoline 在 W-2 Raney nickel 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 反应 2.5h， 生成 (5aR,9aS,10aR)-dodecahydro-5-oxopyrrolo<1,2-b>isoquinoline 、 (5aR,9aS,10aS)-dodecahydro-5-oxopyrrolo<1,2-b>isoquinoline
  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：

  (R)-(+)-甲基对甲苯砜 在 乙基溴化镁 、 二异丙胺 、 lithium diisopropyl amide 作用下， 反应 4.5h， 生成 (5aR,9aR,SS)-1,2,3,5,5a,6,7,8,9,9a-decahydro-10-<(4-methylphenyl)sulfinyl>-5-oxopyrrolo<1,2-b>isoquinoline
  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