(8S,9S,10R,13R,14S,17S)-13-Allyl-17-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-10-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one | 219120-11-3

• 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: (8S,9S,10R,13R,14S,17S)-13-Allyl-17-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-10-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
• CAS: 219120-11-3
• 化学式: C₃₉H₅₀O₃Si
• 分子量: 594.91
• InChiKey: FYDSQAJNWKIPCN-SGZJGLHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8S,9S,10R,13R,14S,17S)-13-Allyl-17-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-10-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以2 mg的产率得到18-vinyl-21-hydroxypregn-5-ene-3,20-dione
  参考文献：
  名称：

  18-Vinyldeoxycorticosterone: a potent inhibitor of the bovine cytochrome P -450 11β

  摘要：

  18-Vinylprogesterone (18-VP) and 18-ethynylprogesterone (18-EP) have proved to be potent suicide inhibitors of P-450(11 beta), the last enzyme of aldosterone biosynthesis (Delorme, C.; Piffeteau, A.; Viger, A.; Marquet, A. fur. J. Biochem. 1995, 232, 247; Delorme, C.; Piffeteau, A.; Sobrio, F.; Marquet, A. fur. J. Biochem. 1997, 248, 252). This paper describes the synthesis of 18-vinyldeoxycorticosterone (18-VDOC), an analogue of deoxycorticosterone (DOC), the physiological substrate of the enzyme, and the evaluation of its reversible inhibiting properties for deoxycorticosterone and corticosterone oxidation by the bovine enzyme. 18-VDOC has been obtained by hydroxylation at C-21 of a 18-VP precursor. Its reversible K-i values are, respectively, 0.3 mu M for the 11 beta-hydroxylation and 0.8 mu M for the 18-hydroxylation. Hence, 18-VDOC is the strongest competitive inhibitor of bovine P-450(11 beta) described so far, but in contrast with 18-VP, it does not inhibit more efficiently the 18-hydroxylation than the 11-hydroxylation, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00106-0
• 作为产物：
  描述：

  1-[(3S,8S,9S,10R,13R,14S,17S)-13-Allyl-10-methyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethanone 在 吡啶 、 N-甲基-4-哌啶酮 、 4-二甲氨基吡啶 、 aluminum isopropoxide 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 126.0h， 生成 (8S,9S,10R,13R,14S,17S)-13-Allyl-17-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-10-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  18-Vinyldeoxycorticosterone: a potent inhibitor of the bovine cytochrome P -450 11β

  摘要：

  18-Vinylprogesterone (18-VP) and 18-ethynylprogesterone (18-EP) have proved to be potent suicide inhibitors of P-450(11 beta), the last enzyme of aldosterone biosynthesis (Delorme, C.; Piffeteau, A.; Viger, A.; Marquet, A. fur. J. Biochem. 1995, 232, 247; Delorme, C.; Piffeteau, A.; Sobrio, F.; Marquet, A. fur. J. Biochem. 1997, 248, 252). This paper describes the synthesis of 18-vinyldeoxycorticosterone (18-VDOC), an analogue of deoxycorticosterone (DOC), the physiological substrate of the enzyme, and the evaluation of its reversible inhibiting properties for deoxycorticosterone and corticosterone oxidation by the bovine enzyme. 18-VDOC has been obtained by hydroxylation at C-21 of a 18-VP precursor. Its reversible K-i values are, respectively, 0.3 mu M for the 11 beta-hydroxylation and 0.8 mu M for the 18-hydroxylation. Hence, 18-VDOC is the strongest competitive inhibitor of bovine P-450(11 beta) described so far, but in contrast with 18-VP, it does not inhibit more efficiently the 18-hydroxylation than the 11-hydroxylation, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00106-0