(5α,13α,14β)-14,17-epoxy-23-hydroxy-4,4,8-trimethyl-16,24-cyclo-13,17-secochola-16,20(22),23-trien-3-one | 183072-28-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5α,13α,14β)-14,17-epoxy-23-hydroxy-4,4,8-trimethyl-16,24-cyclo-13,17-secochola-16,20(22),23-trien-3-one
• 英文别名: (2R,4'aR,4'bR,7'S,8'aR,10'aR)-5-hydroxy-1',1',4'a,7,7',8'a-hexamethylspiro[3H-1-benzofuran-2,8'-4,4b,5,6,7,9,10,10a-octahydro-3H-phenanthrene]-2'-one
• CAS: 183072-28-8
• 化学式: C₂₇H₃₈O₃
• 分子量: 410.597
• InChiKey: OQOGUNVGUJIIKN-WPMRXPNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5α,13α,14β)-14,17-epoxy-23-hydroxy-4,4,8-trimethyl-16,24-cyclo-13,17-secochola-16,20(22),23-trien-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以90%的产率得到(-)-epistypodiol
  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：

  (5R,6R)-6-(3,3-diethoxypropyl)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one 在 盐酸 、 碲化氢 、 sodium tetrahydroborate 、 diethylzinc 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 lithium 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 methyloxirane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 180.92h， 生成 (5α,13α,14β)-14,17-epoxy-23-hydroxy-4,4,8-trimethyl-16,24-cyclo-13,17-secochola-16,20(22),23-trien-3-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.