3β-hydroxy-4,4,17-trimethyl-(8α,13α,14β)-D-homo-androsta-9(11),16-diene-15,17a-dione | 140375-36-6

• 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: 3β-hydroxy-4,4,17-trimethyl-(8α,13α,14β)-D-homo-androsta-9(11),16-diene-15,17a-dione
• CAS: 140375-36-6
• 化学式: C₂₃H₃₂O₃
• 分子量: 356.505
• InChiKey: AIYMKWZOIVBTQV-PZRAEWHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  26.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-4,4,17-trimethyl-(8α,13α,14β)-D-homo-androsta-9(11),16-diene-15,17a-dione 在 三氟化硼 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (2S,4aR,4bR,6aR,8S,10aS,12aR)-2-(2-[1,3]Dithian-2-yl-ethyl)-8-hydroxy-2,7,7,10a,12a-pentamethyl-2,3,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-tetradecahydro-chrysene-1,4-dione
  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-(8α,13α,14α)-D-homoandrosta-9(11),16-diene-15,17a-dione 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到3β-hydroxy-4,4,17-trimethyl-(8α,13α,14β)-D-homo-androsta-9(11),16-diene-15,17a-dione
  参考文献：
  名称：

  关于阿硼烷和戊烷家族的五环三萜全合成的研究

  摘要：

  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。

  DOI：

  10.1016/0040-4020(95)00530-l

文献信息

• Synthetic approaches to pentacyclic triterpenes of the arborane family II1 - @Tetracyclic intermediates
  作者：Siméon Arséniyadis、Ricardo Rodriguez、Rolando Spanevello、José Camara、Adrian Thompson、Eric Guittet、Guy Ourisson

  DOI：10.1016/s0040-4020(01)90787-2

  日期：1992.1

  Diels-Alder condensation of the bicyclic diene 1 with 2,6-dimethylbenzoquinone 2 under thermal and Lewis acid-catalyzed conditions gives the diastereomers 3, 4, 5 and 8; their structures are demonstrated by NMR analysis, in full agreement with the conformations deduced from molecular mechanics.
• 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.