2-Acetoxy-3-phenylpropansaeureethylester | 29169-13-9

• 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: 2-Acetoxy-3-phenylpropansaeureethylester
• 英文别名: rac.-3-Phenyl-2-acetoxy-propionsaeure-ethylester；D,L-α-Acetoxy-β-phenyl-propionsaeure-aethylester；2-acetoxy-3-phenyl-propionic acid ethyl ester；2-Acetoxy-3-phenyl-propionsaeure-aethylester；Ethyl 2-acetyloxy-3-phenylpropanoate
• CAS: 29169-13-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: NPZXJVJAHYWLJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-Acetoxy-3-phenylpropansaeureethylester 、 lithium methanolate 以 甲醇 为溶剂， 生成 甲基2-羟基-3-苯丙酸酯
  参考文献：
  名称：

  Oxidation of α-Acetoxy Acetals with Trichloroisocyanuric Acid

  摘要：

  alpha-Acetoxy acid methyl esters are prepared in excellent yields by treating aliphatic alpha-acetoxy dimethyl acetals with trichloroisocyanuric acid in DMF.

  DOI：

  10.1080/00397919508013870
• 作为产物：
  描述：

  Acetic acid 1-[1,3]dioxolan-2-yl-2-phenyl-ethyl ester 在 三氯异氰尿酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-Acetoxy-3-phenylpropansaeureethylester
  参考文献：
  名称：

  Oxidation of α-Acetoxy Acetals with Trichloroisocyanuric Acid

  摘要：

  alpha-Acetoxy acid methyl esters are prepared in excellent yields by treating aliphatic alpha-acetoxy dimethyl acetals with trichloroisocyanuric acid in DMF.

  DOI：

  10.1080/00397919508013870

文献信息

• Oxidation of 1,3-dicarbonyl compounds using (camphorylsulfonyl)oxaziridines
  作者：Franklin A. Davis、Hu Liu、Bang-Chi Chen、Ping Zhou

  DOI：10.1016/s0040-4020(98)00500-6

  日期：1998.8

  The oxidation of 1,3-dicarbonyl compounds with (camphorylsulfonyl)oxaziridines 2 was studied in both cyclic and acyclic systems. Two reaction pathways were identified: enolate α-hydroxylation and a novel Baeyer-Villiger type oxidation. The Baeyer-Villiger oxidation product was observed only for the ketones and arises via rearrangement of an alkoxy epoxide. Synthetically useful ee's (82–95%) were observed

  在环状和非环状体系中都研究了（樟脑磺酰基）恶二吡啶2对1，3-二羰基化合物的氧化作用。确定了两个反应途径：烯醇化α-羟基化反应和新型Baeyer-Villiger型氧化反应。仅对酮观察到了Baeyer-Villiger氧化产物，并且是通过烷氧基环氧化物的重排而产生的。仅在酮基为6元环的一部分的β-酮酸酯的烯醇化物中观察到合成有用的ee（82–95％）。
• Synthesis of α-diazoesters from α-hydrazonoesters: Utilization of α-hydrazonoesters and α-diazoesters for convenient interconversion
  作者：Eiko Yasui、Kanako Ishimine、Sohta Nitanai、Nanami Hatakeyama、Shinji Nagumo

  DOI：10.1016/j.tetlet.2022.153730

  日期：2022.4

  We have developed a novel method to synthesize α-diazoesters from α-hydrazonoesters with a catalytic amount of Cu(OAc)2 in acetonitrile. When the reaction was carried out under an argon atmosphere, the reaction stopped halfway, suggesting that this reaction required oxygen to reoxidize the catalyst. Since hydrazonoesters can be obtained by reduction of α-diazoesters with P(n-Bu)3 in diisopropyl ether

  我们开发了一种在乙腈中催化量的 Cu(OAc) 2由 α-肼酯合成 α-重氮酯的新方法。当反应在氩气氛下进行时，反应中途停止，表明该反应需要氧气来重新氧化催化剂。由于可以通过在二异丙醚中用 P( n - Bu) 3还原 α-重氮酯来获得肼酯，因此这两种化合物很容易相互转化。α-重氮酯不稳定且不适合储存，而肼酯更稳定，尤其是结晶肼酯。因此，适合长期储存的腙酸酯可以方便地用作α-重氮酯的前体。
• Mild air-oxidation of 1,3-dicarbonyl compounds with cesium salts: Novel α-hydroxylation accompanied by partial hydrolysis of malonate derivatives
  作者：Toshiko Watanabe、Tsutomu Ishikawa

  DOI：10.1016/s0040-4039(99)01618-4

  日期：1999.10

  13-Dicarbonyl compounds (1) were: efficiently oxygenated at the alpha-position with cesium salts, such as CsF or Cs2CO3 (0.1 Meq) in DMF at room temperature. Reaction of malonate derivatives (1a, b) with excess amount (2 Meg) of Cs2CO3 gave alpha-hydroxylmonoester (3) formed by oxygenation and partial hydrolysis, which was decarboxylated to a lactic acid derivative (5). (C) 1999 Elsevier Science Ltd. All rights reserved.
• Gault; Weick, Bulletin de la Societe Chimique de France, 1922, vol. <4> 31, p. 1007,1008
  作者：Gault、Weick

  DOI：——

  日期：——
• US4194051A
  申请人：——

  公开号：US4194051A

  公开（公告）日：1980-03-18