(1S,3aR,4R,7aS)-4-(benzenesulfonylmethyl)-7a-methyl-1-[(2S)-6-methylheptan-2-yl]-2,3,3a,4,6,7-hexahydro-1H-inden-5-one | 1019672-52-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3aR,4R,7aS)-4-(benzenesulfonylmethyl)-7a-methyl-1-[(2S)-6-methylheptan-2-yl]-2,3,3a,4,6,7-hexahydro-1H-inden-5-one
• CAS: 1019672-52-6
• 化学式: C₂₅H₃₈O₃S
• 分子量: 418.641
• InChiKey: DHPJJBPUOCQFSX-CFBSLSOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3aR,4R,7aS)-4-(benzenesulfonylmethyl)-7a-methyl-1-[(2S)-6-methylheptan-2-yl]-2,3,3a,4,6,7-hexahydro-1H-inden-5-one 、 methyl 6-(2-methyl-1,3-dioxolan-2-yl)-3-oxohexanoate 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 苯 、 水 为溶剂， 20.0~80.0 ℃ 、26.66 Pa 条件下， 反应 15.0h， 以71%的产率得到[3S-(3α,3aα,9aα,9bβ)]-3-[(S)-(1,5-dimethylhexyl)]-1,2,3,3a,4,5,8,9,9a,9b-decahydro-3a-methyl-6-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-7H-benz[e]inden-7-one
  参考文献：
  名称：

  A Concise Synthesis of ent-Cholesterol

  摘要：

  ent-Cholesterol was synthesized in 16 steps,from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.

  DOI：

  10.1021/jo702694g
• 作为产物：
  描述：

  (1S,7aS)-4-(benzenesulfonylmethyl)-7a-methyl-1-[(2S)-6-methylheptan-2-yl]-2,3,6,7-tetrahydro-1H-inden-5-one 在 palladium on activated charcoal 氢气 作用下， 以 盐酸 、 甲醇 、 溶剂黄146 为溶剂， 反应 12.0h， 以71%的产率得到(1S,3aR,4R,7aS)-4-(benzenesulfonylmethyl)-7a-methyl-1-[(2S)-6-methylheptan-2-yl]-2,3,3a,4,6,7-hexahydro-1H-inden-5-one
  参考文献：
  名称：

  A Concise Synthesis of ent-Cholesterol

  摘要：

  ent-Cholesterol was synthesized in 16 steps,from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.

  DOI：

  10.1021/jo702694g

文献信息

• A Concise Synthesis of <i>ent</i>-Cholesterol
  作者：Jitendra D. Belani、Scott D. Rychnovsky

  DOI：10.1021/jo702694g

  日期：2008.4.1

  ent-Cholesterol was synthesized in 16 steps,from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.