Ethyl (5α,17β)-17-(acetoxy)androst-2-eno<3,2-b>thiophene-5'-carboxylate | 135643-84-4

• 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: Ethyl (5α,17β)-17-(acetoxy)androst-2-eno<3,2-b>thiophene-5'-carboxylate
• 英文别名: Ethyl (5α,17β)-17-(acetoxy)androst-2-eno[3,2-b]thiophene-5'-carboxylate；ethyl (1S,2S,10S,13R,14S,17S,18S)-17-acetyloxy-2,18-dimethyl-7-thiapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-diene-6-carboxylate
• CAS: 135643-84-4
• 化学式: C₂₆H₃₆O₄S
• 分子量: 444.635
• InChiKey: CHLDOESUOUTDHL-VDTXGSSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Ethyl (5α,17β)-17-(acetoxy)androst-2-eno<3,2-b>thiophene-5'-carboxylate 在 喹啉 、 氢氧化钾 、 铜 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.42h， 生成 (5α,17β)-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
• 作为产物：
  描述：

  17β-Acetoxy-3-chlor-2-formyl-5α-androst-2-en 、 巯基乙酸乙酯 在 吡啶 、 sodium hydride 、 三乙胺 作用下， 生成 Ethyl (5α,17β)-17-(acetoxy)androst-2-eno<3,2-b>thiophene-5'-carboxylate
  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：——