(1R,3aS,3bR,5aS,10aS,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-8-methylsulfanyl-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-9-oxa-dicyclopenta[a,h]phenanthren-1-ol | 135643-93-5

• 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: (1R,3aS,3bR,5aS,10aS,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-8-methylsulfanyl-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-9-oxa-dicyclopenta[a,h]phenanthren-1-ol
• CAS: 135643-93-5
• 化学式: C₂₄H₃₂O₂S
• 分子量: 384.583
• InChiKey: GBAKOWIAICNTTQ-KLYHJYOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,3aS,3bR,5aS,10aS,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-8-methylsulfanyl-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-9-oxa-dicyclopenta[a,h]phenanthren-1-ol 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以23%的产率得到(5α,17α)-5'-(Methylsulfonyl)pregn-2-en-20-yno<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：

  (1S,2S,10S,13R,14S,17S,18S)-2,18-dimethyl-5-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),6-dien-17-ol 在 正丁基锂 、 N,N-二异丙基乙胺 、 三氟乙酸酐 作用下， 反应 21.17h， 生成 (1R,3aS,3bR,5aS,10aS,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-8-methylsulfanyl-2,3,3a,3b,4,5,5a,6,10,10a,10b,11,12,12a-tetradecahydro-1H-9-oxa-dicyclopenta[a,h]phenanthren-1-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