(1S,3aS,3bR,5aS,10aS,10bS,12aS)-10a,12a-Dimethyl-8-methylsulfanyl-1-(tetrahydro-pyran-2-yloxy)-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-7-oxa-dicyclopenta[a,h]phenanthrene | 141469-80-9

• 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: (1S,3aS,3bR,5aS,10aS,10bS,12aS)-10a,12a-Dimethyl-8-methylsulfanyl-1-(tetrahydro-pyran-2-yloxy)-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-7-oxa-dicyclopenta[a,h]phenanthrene
• CAS: 141469-80-9
• 化学式: C₂₇H₄₀O₃S
• 分子量: 444.679
• InChiKey: JWVBIIRBLNOTDS-VMMVKFSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  31.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,3aS,3bR,5aS,10aS,10bS,12aS)-10a,12a-Dimethyl-8-methylsulfanyl-1-(tetrahydro-pyran-2-yloxy)-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-7-oxa-dicyclopenta[a,h]phenanthrene 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (5α,17β)-5'-(Methylsulfonyl)androst-2-eno<3,2-b>furan-17-ol
  参考文献：
  名称：

  Synthesis and androgen receptor affisity of steroidal methylsulfonylforans and a menthylsulfonylthiophene

  摘要：

  Syntheses of the unsubstituted steroidal [3,2-b]furan (3a), thiophene (3b) and [2,3-b]furan (24) are described. Lithiation of the THP ethers 18a and 18b followed by the reaction with methyl disulfide and deprotection gave the 5'-methylsulfide derivatives 19a and 19b. Oxidation of the sulfides and ethynylation provided the compounds 2a and 2b. Swern oxidation of the [2,3-b]furan 24 with DMSO/TFAA/diisopropylethylamine resulted in oxidation to the 17-ketone and introduction of a 5'-methylthio group to give 25. Ethynylation at C-17 followed by oxidation of the sulfide group provided the product 27. 5'-Methylsulfonyl[3,2-b]furanosteroid 2a bound to the rat ventral prostate androgen receptor. However, the corresponding thiophene 2b and the [2,3-b]furan 27 lacked affinity for the receptor.

  DOI：

  10.1016/s0040-4020(01)87122-2
• 作为产物：
  描述：

  雄诺龙 在 4-甲基苯磺酸吡啶 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 四甲基乙二胺 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 30.5h， 生成 (1S,3aS,3bR,5aS,10aS,10bS,12aS)-10a,12a-Dimethyl-8-methylsulfanyl-1-(tetrahydro-pyran-2-yloxy)-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-7-oxa-dicyclopenta[a,h]phenanthrene
  参考文献：
  名称：

  Synthesis and androgen receptor affisity of steroidal methylsulfonylforans and a menthylsulfonylthiophene

  摘要：

  Syntheses of the unsubstituted steroidal [3,2-b]furan (3a), thiophene (3b) and [2,3-b]furan (24) are described. Lithiation of the THP ethers 18a and 18b followed by the reaction with methyl disulfide and deprotection gave the 5'-methylsulfide derivatives 19a and 19b. Oxidation of the sulfides and ethynylation provided the compounds 2a and 2b. Swern oxidation of the [2,3-b]furan 24 with DMSO/TFAA/diisopropylethylamine resulted in oxidation to the 17-ketone and introduction of a 5'-methylthio group to give 25. Ethynylation at C-17 followed by oxidation of the sulfide group provided the product 27. 5'-Methylsulfonyl[3,2-b]furanosteroid 2a bound to the rat ventral prostate androgen receptor. However, the corresponding thiophene 2b and the [2,3-b]furan 27 lacked affinity for the receptor.

  DOI：

  10.1016/s0040-4020(01)87122-2