(5α,17β)-5'-(Methylthio)androst-2-eno<3,2-b>thiophene-17-ol | 135643-97-9

• 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: (5α,17β)-5'-(Methylthio)androst-2-eno<3,2-b>thiophene-17-ol
• 英文别名: (5α,17β)-5'-(Methylthio)androst-2-eno[3,2-b]thiophene-17-ol；(1S,2S,10S,13R,14S,17S,18S)-2,18-dimethyl-6-methylsulfanyl-7-thiapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol
• CAS: 135643-97-9
• 化学式: C₂₂H₃₂OS₂
• 分子量: 376.627
• InChiKey: CJEOCFSTWLXGFA-XNRHGJAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5α,17β)-5'-(Methylthio)androst-2-eno<3,2-b>thiophene-17-ol 在 正丁基锂 、 二甲基亚砜 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 (5α,17α)-5'-(Methylsulfonyl)pregn-2-en-20-yno<3,2-b>thiophene-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：

  (5α,17β)-Androst-2-eno<3,2-b>thiophene-17-ol 在 4-甲基苯磺酸吡啶 正丁基锂 、 四甲基乙二胺 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (5α,17β)-5'-(Methylthio)androst-2-eno<3,2-b>thiophene-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

文献信息

• KUMAR, VIRENDRA;DAUM, SOL J.;BELL, MALCOLM R.;ALEXANDER, MICHAEL A.;CHRIS+, TETRAHEDRON, 47,(1991) N8, C. 5099-5110
  作者：KUMAR, VIRENDRA、DAUM, SOL J.、BELL, MALCOLM R.、ALEXANDER, MICHAEL A.、CHRIS+

  DOI：——

  日期：——