2-phenyl-2-acetoxyethyl benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-2-acetoxyethyl benzoate
• 英文别名: (2-Acetyloxy-2-phenylethyl) benzoate
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: ASNBFMLGNWSNHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-2-acetoxyethyl benzoate 在 二氯二茂锆 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到2-hydroxy-2-phenylethyl benzoate
  参考文献：
  名称：

  Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides

  摘要：

  A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.

  DOI：

  10.1021/acs.orglett.8b03947
• 作为产物：
  描述：

  2-chloromethyl-4-phenyl-1,3-dioxolane 在 potassium tert-butylate 、 甲基三辛基氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-phenyl-2-acetoxyethyl benzoate
  参考文献：
  名称：

  通过环丁烯缩醛中间体对二元醇进行选择性二酯化。

  摘要：

  DOI：

  10.1021/jo990227g

文献信息

• Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides
  作者：Marine Gavel、Thibaut Courant、Antoine Yvan Philippe Joosten、Thomas Lecourt

  DOI：10.1021/acs.orglett.8b03947

  日期：2019.4.5

  A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.
• Selective Diesterification of Diols through Cyclic Ketene Acetal Intermediates
  作者：Zhihong Wu、Roy R. Stanley、Charles U. Pittman

  DOI：10.1021/jo990227g

  日期：1999.10.1