(SR,15S,20R)-3,14-didehydro-14-<(4-methylphenyl)sulfinyl>alloyohimban | 137119-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (SR,15S,20R)-3,14-didehydro-14-<(4-methylphenyl)sulfinyl>alloyohimban
• 英文别名: (15R,20S)-21-[(R)-(4-methylphenyl)sulfinyl]-11,12,15,16,17,18,19,20-octahydro-3H-yohimban-14-one
• CAS: 137119-64-3
• 化学式: C₂₆H₂₆N₂O₂S
• 分子量: 430.571
• InChiKey: UHTOLRZPMAZJKC-XYTRMVCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  53.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (SR,15S,20R)-3,14-didehydro-14-<(4-methylphenyl)sulfinyl>alloyohimban 在 W-2 Raney nickel 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到(+)-alloyohimban-21-one
  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)-(+)-对甲苯亚磺酸D-甲酯 在 lithium diisopropyl amide 作用下， 反应 16.25h， 生成 (SR,15S,20R)-3,14-didehydro-14-<(4-methylphenyl)sulfinyl>alloyohimban
  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