(5R,8R,9S,10S,13R,14S)-10,13-dimethylspiro[1,2,3,4,5,6,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthrene-7,2'-1,3-dioxolane] | 500116-87-0

• 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: (5R,8R,9S,10S,13R,14S)-10,13-dimethylspiro[1,2,3,4,5,6,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthrene-7,2'-1,3-dioxolane]
• CAS: 500116-87-0
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: RFGGRQRBULVVHB-HLXURNFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R,8R,9S,10S,13R,14S)-10,13-dimethylspiro[1,2,3,4,5,6,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthrene-7,2'-1,3-dioxolane] 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 5α-androst-16-en-7-one
  参考文献：
  名称：

  Synthesis and preliminary odour evaluation of 5α-androst-16-en-7-one: a new androstenone analogue

  摘要：

  5alpha-Androst-16-en-3-one has been prepared from 5alpha-androstane-7,17-dione in a five-step sequence, via selective ketalisation at C-7 with bis-trimethylsilyloxyethane and trimethylsilyl triflate as the key step, followed by introduction of the Delta(16) bond by reaction of the 17-hydrazone with iodine to give the vinyl iodide, and deiodination with sodium in ethanol, with acid-catalysed deprotection of the 7-oxo group as the final step. The compound has a mild sandalwood odour. (C) 200 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02430-9
• 作为产物：
  描述：

  5α-androstane-7,17-dione 在 三氟甲磺酸三甲基硅酯 、 碘 、 sodium 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (5R,8R,9S,10S,13R,14S)-10,13-dimethylspiro[1,2,3,4,5,6,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthrene-7,2'-1,3-dioxolane]
  参考文献：
  名称：

  Synthesis and preliminary odour evaluation of 5α-androst-16-en-7-one: a new androstenone analogue

  摘要：

  5alpha-Androst-16-en-3-one has been prepared from 5alpha-androstane-7,17-dione in a five-step sequence, via selective ketalisation at C-7 with bis-trimethylsilyloxyethane and trimethylsilyl triflate as the key step, followed by introduction of the Delta(16) bond by reaction of the 17-hydrazone with iodine to give the vinyl iodide, and deiodination with sodium in ethanol, with acid-catalysed deprotection of the 7-oxo group as the final step. The compound has a mild sandalwood odour. (C) 200 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02430-9

文献信息

• Synthesis and preliminary odour evaluation of 5α-androst-16-en-7-one: a new androstenone analogue
  作者：John A.S. Adams、Scott Clunas、Alan B. Turner

  DOI：10.1016/s0040-4039(02)02430-9

  日期：2002.12

  5alpha-Androst-16-en-3-one has been prepared from 5alpha-androstane-7,17-dione in a five-step sequence, via selective ketalisation at C-7 with bis-trimethylsilyloxyethane and trimethylsilyl triflate as the key step, followed by introduction of the Delta(16) bond by reaction of the 17-hydrazone with iodine to give the vinyl iodide, and deiodination with sodium in ethanol, with acid-catalysed deprotection of the 7-oxo group as the final step. The compound has a mild sandalwood odour. (C) 200 Elsevier Science Ltd. All rights reserved.