(乙酰氧基-羟基磷酰)乙酸酯 | 3614-36-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: (乙酰氧基-羟基磷酰)乙酸酯
• 英文名称: diacetyl-phosphoric acid
• 英文别名: Diacetyl-phosphorsaeure；diacetyl phosphate；[acetyloxy(hydroxy)phosphoryl] acetate
• CAS: 3614-36-6
• 化学式: C₄H₇O₆P
• 分子量: 182.07
• InChiKey: XLLNINGEDIOQGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trifluoroacetic anhydride 、 (乙酰氧基-羟基磷酰)乙酸酯 生成 Triacetylphosphat
  参考文献：
  名称：

  Toward a Clean Alternative to Friedel−Crafts Acylation:  In Situ Formation, Observation, and Reaction of an Acyl Bis(trifluoroacetyl)phosphate and Related Structures

  摘要：

  Reaction of acyl trifluoroacetates with phosphoric acid in the presence of trifluoroacetic anhydride (TFAA) leads to the ready formation of acyl bis(trifluoroacetyl)phosphates, which are powerful acylating agents. Formation of these species and the subsequent acylation reaction are carried out, without added solvent, in a single in situ reaction process. In this reaction system, anisole is rapidly acylated at ambient temperature using a variety of carboxylic acids giving the para isomer exclusively. TFAA acts as an activating agent and can be recovered from the reaction system as trifluoroacetic acid (TFA) and converted back to TFAA using a dehydrating agent, while phosphoric acid behaves as a covalent catalyst in the process. This reaction system has many features which are required elements of a clean alternative to the Friedel-Crafts process.

  DOI：

  10.1021/jo981264v
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 (乙酰氧基-羟基磷酰)乙酸酯
  参考文献：
  名称：

  Lynen, Chemische Berichte, 1940, vol. 73, p. 367,368, 373

  摘要：

  DOI：

文献信息

• Evaluation of Natural and Synthetic Phosphate Donors for the Improved Enzymatic Synthesis of Phosphate Monoesters
  作者：Gábor Tasnádi、Wolfgang Jud、Mélanie Hall、Kai Baldenius、Klaus Ditrich、Kurt Faber

  DOI：10.1002/adsc.201800306

  日期：2018.6.15

  obstacles associated with the use of pyrophosphate in the phosphatase‐catalyzed synthesis of phosphate monoesters on large scale. In order to overcome both limitations, we screened a broad range of natural and synthetic organic phosphate donors with several enzymes on a broad variety of hydroxyl‐compounds. Among them, acetyl phosphate delivered stable product levels and high phospho‐transfer efficiency at

  不期望的产物水解以及大量无机单磷酸酯副产物形式的废物是在磷酸酶催化的磷酸单酯大规模合成中使用焦磷酸盐的主要障碍。为了克服这两个限制，我们用多种酶对多种羟基化合物筛选了多种天然和合成的有机磷酸盐供体。其中，乙酰磷酸在较低的功能 pH 限制下提供稳定的产品水平和高磷酸转移效率，这转化为出色的生产率。该方案通常适用于酸性磷酸酶，并与一系列不同的底物兼容。使用廉价起始材料合成的乙酰磷酸盐进行制备规模转化，产生了多克各种糖磷酸盐，时空产率高达 433 g L -1 h -1 ，并且磷酸钡废物减少了 75%。
• Nucleophilic reactivity toward acetyl chloride in water
  作者：David Palling、William P. Jencks

  DOI：10.1021/ja00329a040

  日期：1984.8