3-(乙酰氧基)-3-苯基丙酸甲酯 | 90104-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(乙酰氧基)-3-苯基丙酸甲酯
• 英文名称: methyl 3-(acetyloxy)-3-phenylpropanoate
• 英文别名: methyl 3-acetoxy-3-phenylpropanoate；3-acetoxy-3-phenylpropionate；3-acetoxy-3-phenyl-propionic acid methyl ester；3-Acetoxy-3-phenyl-propionsaeure-methylester；3-acetoxy-3-phenylpropionic acid methyl ester；Methyl 3-acetyloxy-3-phenylpropanoate
• CAS: 90104-62-4
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: SJFPCVMQBJCMAU-UHFFFAOYSA-N

物化性质

• 沸点：
  84 °C(Press: 0.03 Torr)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-(乙酰氧基)-3-苯基丙酸甲酯 在 三乙胺盐酸盐 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 3-羟基-3-苯基丙酸甲酯
  参考文献：
  名称：

  Garay, Raul O.; Cabaleiro, Mercedes C., Journal of the Chemical Society. Perkin transactions II, 1988, p. 1643 - 1648

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰乙酸甲酯 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-(乙酰氧基)-3-苯基丙酸甲酯
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

  摘要：

  Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.004

文献信息

• Palladium-Catalyzed Three-Component Coupling Reactions: 1,1-Difunctionalization of Activated Alkenes
  作者：Arantxa Rodriguez、Wesley J. Moran

  DOI：10.1002/ejoc.200801245

  日期：2009.3

  A three-component coupling reaction was developed to access 3,3-oxyarylpropionate derivatives. Each of the three reaction components can be varied, allowing the modular synthesis of a range of important chiral building blocks. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  开发了一种三组分偶联反应来获得 3,3-氧芳基丙酸酯衍生物。三个反应组分中的每一个都可以变化，从而允许模块化合成一系列重要的手性构件。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Tungsten and molybdenum 2-oxaallyl [.eta.1-(C)-enolate] complexes: functional group transformations, photochemical aldol reactions, and alkyne/carbon monoxide migratory insertion reactions
  作者：Elizabeth R. Burkhardt、Jeffrey J. Doney、Robert G. Bergman、Clayton H. Heathcock

  DOI：10.1021/ja00241a020

  日期：1987.4

  Preparation des complexes oxa-2alkyl (η 1 -enolate) par reaction de C 5 R 5 (CO) 3 M − Ne + avec les α-chloroesters, les cetones et les amides. Structures cristallines de certains complexes

  C 5 R 5 (CO) 3 M - Ne + avec les α-氯酯、les cetones 和 les 酰胺的合成 oxa-2 烷基 (η 1 -烯醇化物) par 反应的制备。某些复合体的晶体结构
• Selective benzylic C–H monooxygenation mediated by iodine oxides
  作者：Kelsey B LaMartina、Haley K Kuck、Linda S Oglesbee、Asma Al-Odaini、Nicholas C Boaz

  DOI：10.3762/bjoc.15.55

  日期：——

  for the selective monooxdiation of secondary benzylic C–H bonds is described using an N-oxyl catalyst and a hypervalent iodine species as a terminal oxidant. Combinations of ammonium iodate and catalytic N-hydroxyphthalimide (NHPI) were shown to be effective in the selective oxidation of n-butylbenzene directly to 1-phenylbutyl acetate in high yield (86%). This method shows moderate substrate tolerance

  描述了一种使用N-氧基催化剂和高价碘物种作为末端氧化剂对仲苄基CH键进行选择性一氧化的方法。碘酸铵和催化N-羟基邻苯二甲酰亚胺（NHPI）的组合被证明对n的选择性氧化有效丁苯直接以高产率（86％）转化为乙酸1-苯丁酯。该方法在含仲苄基CH键的底物的氧合中显示出适度的底物耐受性，从而以良好至中等的产率产生了相应的乙酸苄酯。尽管C–H键较弱，但在类似条件下叔苄基C–H键仍无反应。初步的机理分析表明，该NHPI-碘酸盐系统通过基于自由基的机制起作用，其中原位产生的碘捕获形成的苄基自由基。然后将苄基碘化物中间体溶剂分解以产生产物酯。
• Removal of zinc salts from nonaqueous synthesis solutions comprising zinc alkoxides or zinc amides
  申请人：Consortium fur elecktrochemische Industrie GmbH & Co. KG

  公开号：US20040089613A1

  公开（公告）日：2004-05-13

  A process for removing zinc from organic solutions comprising zinc alkoxides or zinc amides, includes admixing the solution with an alkylating, arylating, acylating or silylating agent in the presence of a precipitating reagent having at least two nitrogen donors and subsequently removing the precipitated solid.

  一种从含有锌烷氧化物或锌酰胺的有机溶液中去除锌的方法，包括将该溶液与烷基化、芳基化、酰化或硅基化试剂混合，同时加入至少具有两个氮供体的沉淀试剂，然后去除沉淀的固体。
• Electrochemical Benzylic C(sp³)–H Acyloxylation
  作者：Alexander P. Atkins、Albert C. Rowett、David M. Heard、Joseph A. Tate、Alastair J. J. Lennox

  DOI：10.1021/acs.orglett.2c01930

  日期：2022.7.22

  The development of sustainable C(sp3)–H functionalization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters

  可持续的 C(sp 3 )-H 官能化方法的开发对制药和农用化学工业非常感兴趣。阳极氧化是产生苄基阳离子的有效方法，该阳离子可以进行随后的原位亲核攻击以提供官能化的苄基产物。在此，我们证明了羧酸作为亲核试剂产生苄酯的适用性。该方法采用一系列次苄基底物和官能化羧酸，并在克级流动中得到证明。