1-(pivaloyloxy)octan-4-ol | 141923-54-8

• 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-(pivaloyloxy)octan-4-ol
• 英文别名: 4-Hydroxyoctyl 2,2-dimethylpropanoate；4-hydroxyoctyl 2,2-dimethylpropanoate
• CAS: 141923-54-8
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: LJFOPTWQHQFLGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基乙酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 42.0h， 生成 1-(pivaloyloxy)octan-4-ol
  参考文献：
  名称：

  Twisted Amides as Selective Acylating Agents for Hydroxyl Groups under Neutral Conditions:  Models for Activated Peptides during Enzymatic Acyl Transfer Reaction

  摘要：

  The highly twisted amide 2 served as a selective acylating agent; for dials under neutral conditions. The reaction of primary-secondary dials with 2 led to the corresponding primary alkyl monopivalates. For dials containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were selectively acylated under neutral conditions, whereas, the opposite selectivity was observed under basic conditions, similar to the cases using acyl halides or acid anhydrides. Although 1 and 3 were unreactive to alcohols, 5-10 having substituent groups at C-4 were reactive to alcohols to give the corresponding acetates or benzoates.

  DOI：

  10.1021/jo9522015

文献信息

• Selective pivaloylation of Hydroxyl Groups by 3-Pivaloyl-1,3-thiazolidine-2-thione Under Neutral Conditions
  作者：Shinji Yamada

  DOI：10.1016/0040-4039(92)88169-6

  日期：1992.4

  conditions, 3-pivaloyl-1,3-thiazolidine-2-thione (PTT) was found to act as a selective pivaloylating reagent for hydroxyl groups. The primary hydroxyl groups of diols containing primary and secondary hydroxyl groups, and the phenolic hydroxyl groups of the diols having alcoholic and phenolic hydroxyl groups were selectively pivaloylated by PTT.

  在中性条件下，发现3-pivaloyl-1,3-thiazolidine-2-thione（PTT）可作为羟基的选择性Pivaloyylating试剂。通过PTT选择性地将含有伯羟基和仲羟基的二醇的伯羟基以及具有醇羟基和酚羟基的二醇的酚羟基进行了多羟基化。
• Twisted Amides as Selective Acylating Agents for Hydroxyl Groups under Neutral Conditions:  Models for Activated Peptides during Enzymatic Acyl Transfer Reaction
  作者：Shinji Yamada、Takayuki Sugaki、Kazuhiro Matsuzaki

  DOI：10.1021/jo9522015

  日期：1996.1.1

  The highly twisted amide 2 served as a selective acylating agent; for dials under neutral conditions. The reaction of primary-secondary dials with 2 led to the corresponding primary alkyl monopivalates. For dials containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were selectively acylated under neutral conditions, whereas, the opposite selectivity was observed under basic conditions, similar to the cases using acyl halides or acid anhydrides. Although 1 and 3 were unreactive to alcohols, 5-10 having substituent groups at C-4 were reactive to alcohols to give the corresponding acetates or benzoates.