(3β,17β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-17-(thien-3-yl)-androst-5-en-17-ol | 167948-83-6

• 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: (3β,17β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-17-(thien-3-yl)-androst-5-en-17-ol
• 英文别名: (3β,17β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-17-(3-thienyl)-androst-5-en-17-ol；(3S,8R,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-17-thiophen-3-yl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
• CAS: 167948-83-6
• 化学式: C₂₉H₄₆O₂SSi
• 分子量: 486.835
• InChiKey: DDSCGGXTTASGKY-TWTOWXJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  57.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3β,17β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-17-(thien-3-yl)-androst-5-en-17-ol 在 氢溴酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以68%的产率得到17-(3'-thienyl)androsta-5,16-dien-3β-ol
  参考文献：
  名称：

  Inhibition of steroid C17(20) lyase with C-17-heteroaryl steroids

  摘要：

  Steroids bearing a heteroaromatic substituent at C-17 were designed as inhibitors of C-17(20) lyase. The thiazoles, furans, and thiophenes appended to the steroid nucleus were positioned on the alpha-face and the beta-face of the steroid, and conjugated with a 16,17-olefin, to test their ability to coordinate the heme iron of the P450 enzyme complex. The position of the heterocycle with respect to the steroid skeleton was determined to be important for optimum affinity and, in general, compounds with the heterocycle attached to a trigonal center at C-17, had the best affinity for C-17(20) lyase. Simple molecular models were used to compare the three types of heterocyclic-substituted steroids. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00135-6
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (3β,17β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-17-(thien-3-yl)-androst-5-en-17-ol
  参考文献：
  名称：

  Inhibition of steroid C17(20) lyase with C-17-heteroaryl steroids

  摘要：

  Steroids bearing a heteroaromatic substituent at C-17 were designed as inhibitors of C-17(20) lyase. The thiazoles, furans, and thiophenes appended to the steroid nucleus were positioned on the alpha-face and the beta-face of the steroid, and conjugated with a 16,17-olefin, to test their ability to coordinate the heme iron of the P450 enzyme complex. The position of the heterocycle with respect to the steroid skeleton was determined to be important for optimum affinity and, in general, compounds with the heterocycle attached to a trigonal center at C-17, had the best affinity for C-17(20) lyase. Simple molecular models were used to compare the three types of heterocyclic-substituted steroids. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00135-6