O-[[(1S,2S,5S)-2-hydroxy-2-methyl-5-(6-methylhepta-1,5-dien-2-yl)cyclopentyl]methyl] methylsulfanylmethanethioate | 1280572-90-8

• 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: O-[[(1S,2S,5S)-2-hydroxy-2-methyl-5-(6-methylhepta-1,5-dien-2-yl)cyclopentyl]methyl] methylsulfanylmethanethioate
• CAS: 1280572-90-8
• 化学式: C₁₇H₂₈O₂S₂
• 分子量: 328.54
• InChiKey: CILXEBSFAJLQOS-INMHGKMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-[[(1S,2S,5S)-2-hydroxy-2-methyl-5-(6-methylhepta-1,5-dien-2-yl)cyclopentyl]methyl] methylsulfanylmethanethioate 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 甲基磺酰胺 、 三正丁基氢锡 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 29.08h， 生成 (1S,2R,3S)-3-[(5R)-5-hydroxy-5-(2-methyloxiran-2-yl)pent-1-en-2-yl]-1,2-dimethylcyclopentan-1-ol
  参考文献：
  名称：

  Protecting-Group-Free Synthesis of Chokols

  摘要：

  As a result of a combined theoretical and experimental study, we describe a two-step protocol for the preparation of an optically pure, multifunctional, cyclopentanic core shared by a number of natural products. This process is based on a hitherto unreported Ti(III)-mediated diastereoselective cyclization in which the hydroxy-directed template effect played by the Ti(III) species was found to be crucial for the stereoselective outcome of the reaction. The viability of this concept was confirmed with the first protecting-group free synthesis of three enantiopure chokols, namely, chokols K, E, and B.

  DOI：

  10.1021/jo102280n
• 作为产物：
  描述：

  (+)-1-hydroxychokol K 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.08h， 生成 O-[[(1S,2S,5S)-2-hydroxy-2-methyl-5-(6-methylhepta-1,5-dien-2-yl)cyclopentyl]methyl] methylsulfanylmethanethioate
  参考文献：
  名称：

  Protecting-Group-Free Synthesis of Chokols

  摘要：

  As a result of a combined theoretical and experimental study, we describe a two-step protocol for the preparation of an optically pure, multifunctional, cyclopentanic core shared by a number of natural products. This process is based on a hitherto unreported Ti(III)-mediated diastereoselective cyclization in which the hydroxy-directed template effect played by the Ti(III) species was found to be crucial for the stereoselective outcome of the reaction. The viability of this concept was confirmed with the first protecting-group free synthesis of three enantiopure chokols, namely, chokols K, E, and B.

  DOI：

  10.1021/jo102280n