(1aS,1bR,3aR,5S,7aR,7bS,9aR)-9a-(tert-Butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-one | 182880-79-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1aS,1bR,3aR,5S,7aR,7bS,9aR)-9a-(tert-Butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-one
• 英文别名: (1aS,1bR,3aR,5S,7aR,7bS,9aR)-9a-[tert-butyl(dimethyl)silyl]oxy-1a,3a,5,7b-tetramethyl-1,1b,2,3,5,6,7,7a,8,9-decahydrocyclopropa[a]phenanthren-4-one
• CAS: 182880-79-1
• 化学式: C₂₅H₄₄O₂Si
• 分子量: 404.709
• InChiKey: FCTHPEIKIRXIIF-DGVWMKDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1aS,1bR,3aR,5S,7aR,7bS,9aR)-9a-(tert-Butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-one 在 盐酸 、 sodium tetrahydroborate 、 lithium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 stypodiol
  参考文献：
  名称：

  An Efficient Stereoselective Synthesis of Stypodiol and Epistypodiol

  摘要：

  An efficient synthesis of stypodiol (1) and its epimer at C-14, epistypodiol (2), was accomplished starting from (S)-(+)-carvone (7). The synthesis of both epimeric compounds proceeds through common intermediates using an IMDA reaction, a sonochemical Barbier reaction, and an acid-catalyzed quinol-tertiary alcohol cyclization as key synthetic steps.

  DOI：

  10.1021/jo980311g
• 作为产物：
  描述：

  (1aS,1bR,3aR,7aR,7bS,9aR)-9a-[tert-butyl(dimethyl)silyl]oxy-1a,3a,5,7b-tetramethyl-1,1b,2,3,7,7a,8,9-octahydrocyclopropa[a]phenanthren-4-one 在 碲化氢 、 sodium tetrahydroborate 、 sodium methylate 作用下， 生成 (1aS,1bR,3aR,5S,7aR,7bS,9aR)-9a-(tert-Butyl-dimethyl-silanyloxy)-1a,3a,5,7b-tetramethyl-tetradecahydro-cyclopropa[a]phenanthren-4-one
  参考文献：
  名称：

  An Efficient Stereoselective Synthesis of Stypodiol and Epistypodiol

  摘要：

  An efficient synthesis of stypodiol (1) and its epimer at C-14, epistypodiol (2), was accomplished starting from (S)-(+)-carvone (7). The synthesis of both epimeric compounds proceeds through common intermediates using an IMDA reaction, a sonochemical Barbier reaction, and an acid-catalyzed quinol-tertiary alcohol cyclization as key synthetic steps.

  DOI：

  10.1021/jo980311g

文献信息

• An Efficient Stereoselective Synthesis of Stypodiol and Epistypodiol
  作者：Antonio Abad、Consuelo Agulló、Manuel Arnó、Ana C. Cuñat、Benjamín Meseguer、Ramón J. Zaragozá

  DOI：10.1021/jo980311g

  日期：1998.7.1

  An efficient synthesis of stypodiol (1) and its epimer at C-14, epistypodiol (2), was accomplished starting from (S)-(+)-carvone (7). The synthesis of both epimeric compounds proceeds through common intermediates using an IMDA reaction, a sonochemical Barbier reaction, and an acid-catalyzed quinol-tertiary alcohol cyclization as key synthetic steps.