(3aS,5aR,5bR,7aR,9S,11aS,13aR)-9-Hydroxy-3a,8,8,11a,13a-pentamethyl-2,3,3a,4,5a,5b,6,7,7a,8,9,10,11,11a,13,13a-hexadecahydro-cyclopenta[a]chrysen-5-one | 147722-28-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3aS,5aR,5bR,7aR,9S,11aS,13aR)-9-Hydroxy-3a,8,8,11a,13a-pentamethyl-2,3,3a,4,5a,5b,6,7,7a,8,9,10,11,11a,13,13a-hexadecahydro-cyclopenta[a]chrysen-5-one
• CAS: 147722-28-9
• 化学式: C₂₆H₃₈O₂
• 分子量: 382.587
• InChiKey: PZZZQASBMJRXOA-IPWKDDGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  28.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3aS,5aR,5bR,7aR,9S,11aS,13aR)-9-Hydroxy-3a,8,8,11a,13a-pentamethyl-2,3,3a,4,5a,5b,6,7,7a,8,9,10,11,11a,13,13a-hexadecahydro-cyclopenta[a]chrysen-5-one 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 (3aS,5aR,5bR,7aR,9S,11aS,13aS,13bR)-9-Hydroxy-3a,8,8,11a,13a-pentamethyl-1,2,3,3a,4,5a,5b,6,7,7a,8,9,10,11,11a,13,13a,13b-octadecahydro-cyclopenta[a]chrysen-5-one
  参考文献：
  名称：

  Diels-Alder approaches to pentacyclic triterpenes of the arborane and the fernane families

  摘要：

  The high pressure Diels-Alder reaction of diene 2 and ene-dione 3 does not lead to the arborane skeleton but to angular isomers 5. The AB + D synthesis of tetracyclic ene-dione 6, followed by construction of the E-ring by a double alkylation, yields the isoarborinol precursor 7; the fernane series is similarly accessed.

  DOI：

  10.1016/s0040-4039(00)77511-3
• 作为产物：
  描述：

  3β-hydroxy-4,4,17-trimethyl-D-homo-androsta-9(11),16-diene-15,17a-dione 在 Ra-Ni 、 三氟化硼 六甲基磷酰三胺 、 cerium(III) chloride 、 叔丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 0.34h， 生成 (3aS,5aR,5bR,7aR,9S,11aS,13aR)-9-Hydroxy-3a,8,8,11a,13a-pentamethyl-2,3,3a,4,5a,5b,6,7,7a,8,9,10,11,11a,13,13a-hexadecahydro-cyclopenta[a]chrysen-5-one
  参考文献：
  名称：

  Diels-Alder approaches to pentacyclic triterpenes of the arborane and the fernane families

  摘要：

  The high pressure Diels-Alder reaction of diene 2 and ene-dione 3 does not lead to the arborane skeleton but to angular isomers 5. The AB + D synthesis of tetracyclic ene-dione 6, followed by construction of the E-ring by a double alkylation, yields the isoarborinol precursor 7; the fernane series is similarly accessed.

  DOI：

  10.1016/s0040-4039(00)77511-3

文献信息

• Studies towards the total synthesis of pentacyclic triterpenes of the arborane and fernane family
  作者：Simeon Arseniyadis、Ricardo Rodriguez、José Camara、Jean F. Gallard、Eric Guittet、Loïc Toupet、Guy Ourisson

  DOI：10.1016/0040-4020(95)00530-l

  日期：1995.1

  Stereo and regrochemcal variations in conjugate addition reactions leading to isoarborinal and fernenol-Hke interpenes via a five-step protccol are described. The Gngnard addition on 9, 10, 15 and 18 served lo establish the relative stereoehemicul details.

  描述了共轭加成反应中的立体变化和再化学变化，这些变化通过五步协议产生异芳烃和蕨烯-Hke萜烯。分别在9、10、15和18上进行的Gngnard加法建立了相对的立体电子学细节。
• Diels-Alder approaches to pentacyclic triterpenes of the arborane and the fernane families
  作者：Simeon Arseniyadis、Ricardo Rodriguez、Jose Camara、Eric Guittet、Loïc Toupet

  DOI：10.1016/s0040-4039(00)77511-3

  日期：1993.2

  The high pressure Diels-Alder reaction of diene 2 and ene-dione 3 does not lead to the arborane skeleton but to angular isomers 5. The AB + D synthesis of tetracyclic ene-dione 6, followed by construction of the E-ring by a double alkylation, yields the isoarborinol precursor 7; the fernane series is similarly accessed.