8-deuterio-3-ethyl-3,8-dodecanodiol | 156340-29-3

• 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: 8-deuterio-3-ethyl-3,8-dodecanodiol
• CAS: 156340-29-3
• 化学式: C₁₄H₃₀O₂
• 分子量: 231.383
• InChiKey: AQIKTWWHDRBHIL-YSOHJTORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  16.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  8-deuterio-3-ethyl-3,8-dodecanodiol 在 磷酸 作用下， 以 甲苯 为溶剂， 以70%的产率得到10-deuterio-10-ethyl-5-dodecanone
  参考文献：
  名称：

  Intramolecular 1,6-hydride transfer in acyclic 1,6-diols: A mechanistic study

  摘要：

  The reaction of acyclic 1,6-diol 11a with 85% phosphoric acid at toluene reflux yields ketone 13a through an intramolecular 1,6-hydride transfer. This fact is proven by using a deuterated 1,6-diol (19), in which the corresponding 1,6-deuteride transfer occurs. A mechanistic proposal through a protonated oxepane (II) is formulated, which implies an actual 1,3-hydride transfer; this mechanism differs from the reported one in the literature for cyclic 1,6-diols, in which a real 1,6-hydride transfer takes place due to a proximity effect.

  DOI：

  10.1016/s0040-4020(01)85254-6
• 作为产物：
  描述：

  2-butyl-2-(4-chlorobutyl)-1,3-dioxolane 在 盐酸 、 lithium aluminium deuteride 、 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 生成 8-deuterio-3-ethyl-3,8-dodecanodiol
  参考文献：
  名称：

  Intramolecular 1,6-hydride transfer in acyclic 1,6-diols: A mechanistic study

  摘要：

  The reaction of acyclic 1,6-diol 11a with 85% phosphoric acid at toluene reflux yields ketone 13a through an intramolecular 1,6-hydride transfer. This fact is proven by using a deuterated 1,6-diol (19), in which the corresponding 1,6-deuteride transfer occurs. A mechanistic proposal through a protonated oxepane (II) is formulated, which implies an actual 1,3-hydride transfer; this mechanism differs from the reported one in the literature for cyclic 1,6-diols, in which a real 1,6-hydride transfer takes place due to a proximity effect.

  DOI：

  10.1016/s0040-4020(01)85254-6

文献信息

• Intramolecular 1,6-hydride transfer in acyclic 1,6-diols: A mechanistic study
  作者：Juan F Gil、Diego J Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(01)85254-6

  日期：1994.1

  The reaction of acyclic 1,6-diol 11a with 85% phosphoric acid at toluene reflux yields ketone 13a through an intramolecular 1,6-hydride transfer. This fact is proven by using a deuterated 1,6-diol (19), in which the corresponding 1,6-deuteride transfer occurs. A mechanistic proposal through a protonated oxepane (II) is formulated, which implies an actual 1,3-hydride transfer; this mechanism differs from the reported one in the literature for cyclic 1,6-diols, in which a real 1,6-hydride transfer takes place due to a proximity effect.