1-(1-(hydroxymethyl)-2-phenylcyclopropyl)octan-2-ol | 1611477-18-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(1-(hydroxymethyl)-2-phenylcyclopropyl)octan-2-ol
• CAS: 1611477-18-9
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: PMXUIKQDYAUJJU-UHFFFAOYSA-N

物化性质

• 沸点：
  410.9±18.0 °C(predicted)
• 密度：
  1.027±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(1-(hydroxymethyl)-2-phenylcyclopropyl)octan-2-ol 在 samarium diiodide 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 2-phenethyldecane-1,4-diol
  参考文献：
  名称：

  Ketyl-Type Radicals from Cyclic and Acyclic Esters are Stabilized by SmI₂(H₂O)_n: The Role of SmI₂(H₂O)_n in Post-Electron Transfer Steps

  摘要：

  Mechanistic details pertaining to the SmI2-H2O-mediated reduction and reductive coupling of 6-membered lactones, the first class of simple unactivated carboxylic acid derivatives that had long been thought to lie outside the reducing range of SmI2, have been elucidated. Our results provide new experimental evidence that water enables the productive electron transfer from Sm(II) by stabilization of the radical anion intermediate rather than by solely promoting the first electron transfer as originally proposed. Notably, these studies suggest that all reactions involving the generation of ketyl-type radicals with SmI2 occur under a unified mechanism based on the thermodynamic control of the second electron transfer step, thus providing a blueprint for the development of a broad range of novel chemoselective transformations via open-shell electron pathways.

  DOI：

  10.1021/ja503494b
• 作为产物：
  描述：

  6-hexyl-1-phenyl-5-oxaspiro[2.4]heptan-4-one 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 5-hexyl-3-phenethyldihydrofuran-2(3H)-one 、 2-phenethyldecane-1,4-diol 、 1-(1-(hydroxymethyl)-2-phenylcyclopropyl)octan-2-ol
  参考文献：
  名称：

  Ketyl-Type Radicals from Cyclic and Acyclic Esters are Stabilized by SmI₂(H₂O)_n: The Role of SmI₂(H₂O)_n in Post-Electron Transfer Steps

  摘要：

  Mechanistic details pertaining to the SmI2-H2O-mediated reduction and reductive coupling of 6-membered lactones, the first class of simple unactivated carboxylic acid derivatives that had long been thought to lie outside the reducing range of SmI2, have been elucidated. Our results provide new experimental evidence that water enables the productive electron transfer from Sm(II) by stabilization of the radical anion intermediate rather than by solely promoting the first electron transfer as originally proposed. Notably, these studies suggest that all reactions involving the generation of ketyl-type radicals with SmI2 occur under a unified mechanism based on the thermodynamic control of the second electron transfer step, thus providing a blueprint for the development of a broad range of novel chemoselective transformations via open-shell electron pathways.

  DOI：

  10.1021/ja503494b