ethyl 3-acetoxy-3-phenylpropionate | 25409-25-0

• 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: ethyl 3-acetoxy-3-phenylpropionate
• 英文别名: ethyl 3-acetoxy-3-phenylpropanoate；Ethyl 3-acetyloxy-3-phenylpropanoate
• CAS: 25409-25-0
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: HNOFMAVEDATAJR-UHFFFAOYSA-N

物化性质

• 沸点：
  114 °C(Press: 0.5 Torr)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：

  ethyl 3-acetoxy-3-phenylpropionate 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 68.0h， 生成 (S)-3-氨基-3-苯基丙酸
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of 3-hydroxy- and 3-amino-3-phenylpropanoic acid

  摘要：

  Ethyl (S)-3-hydroxy-3-phenylpropionate (S)-2 was obtained by the asymmetric reduction of ethyl 3-phenyl-3-oxopropionate 1 with the yeast Saccharomyces cerevisiae (ATCC 9080). The kinetic resolution of racemic ethyl 2-acetoxy-3-phenyl-propionate rac-3 with the same microorganism, gave after hydrolysis ethyl (R)-and (S)-3-hydroxy-3-phenylpropionates (R)-2 and (S)-2 which were converted by a straightforward series of reactions to the enantiomers of 3-amino-3-phenyl-propionic acids (S)-6 and (R)-6. The asymmetric reduction and hydrolytic kinetic resolution were also tested with several other whole cell systems under a variety of conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.007
• 作为产物：
  描述：

  Ethyl 3-phenyl-3-(2-tributylstannylpropan-2-yloxy)propanoate 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到ethyl 3-acetoxy-3-phenylpropionate
  参考文献：
  名称：

  官能团不对称四烷基锡烷酮经臭氧的区域选择性氧化裂解

  摘要：

  描述了通过与臭氧反应将（α-烷氧基烷基）三烷基锡烷直接氧化成酯。

  DOI：

  10.1016/0040-4039(94)88057-3

文献信息

• A new acylation catalyst
  作者：Saeed Ahmad、Javed Iqbal

  DOI：10.1039/c39870000114

  日期：——

  Cobalt(II) chloride catalyses the acylation of alcohols and amines with anhydrides in excellent yields.

  氯化钴（II）以优异的产率催化醇和胺与酸酐的酰化反应。
• A NEW METHOD FOR THE GENERATION OF A BORON ENOLATE OF AN ESTER—A NEW SYNTHESIS OF 2-DEOXY-D-RIBOSE—
  作者：Masahiro Murakami、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.241

  日期：1982.2.5

  and the boron enolate thus formed further reacted with aldehydes to give β-hydroxyesters and β-acetoxyesters in good yields. The reaction was successfully applied to the stereoselective synthesis of 2-deoxy-D-ribose.

  通过用乙酸汞(II)和二苯基硼酸处理乙氧基乙炔，原位生成酯的硼烯醇化物，由此形成的硼烯醇化物与醛进一步反应，以良好的产率得到β-羟基酯和β-乙酰氧基酯。该反应成功应用于2-脱氧-D-核糖的立体选择性合成。
• Organomanganese (II) reagents XX: Manganese mediated Barbier and Reformatsky like reactions an efficient route to homoallylic alcohols and β-acetoxyesters
  作者：Gérard Cahiez、Pierre-Yves Chavant

  DOI：10.1016/s0040-4039(00)70700-3

  日期：1989.1

  Allylic halides and α-bromoesters react with manganese metal in ethyl acetate; THF can also be used as solvent if a catalytic amount of zinc chloride is added to the reaction mixture. When the reaction is performed in the presence of various aldehydes or ketones, excellent yields of 1,2-addition products are obtained in preparative conditions.

  烯丙基卤化物和α-溴酸酯与锰金属在乙酸乙酯中反应；如果将催化量的氯化锌加入到反应混合物中，则THF也可以用作溶剂。当反应在各种醛或酮的存在下进行时，在制备条件下可获得极好的1,2-加成产物收率。
• Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions
  作者：Andrea Temperini、Lucio Minuti、Tommaso Morini、Ornelio Rosati、Francesca Piazzolla

  DOI：10.1016/j.tetlet.2017.09.007

  日期：2017.10

  Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.

  官能化的伯醇，仲醇和叔醇被乙酸异丙烯酯和催化的对-TsOH有效地乙酰化。
• Synthesis of Novel Diastereomeric Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation Reactions
  作者：Liqin Qiu、Jianying Qi、Cheng-Chao Pai、Shusun Chan、Zhongyuan Zhou、Michael C. K. Choi、Albert S. C. Chan

  DOI：10.1021/ol026817+

  日期：2002.12.1

  Diastereomeric biaryl diphosphine ligands 10 and 11 with added chiral centers on the backbone were synthesized. Substrate-directed asymmetric synthesis occurred in the coupling step of the preparation of the diastereomeric diphosphine oxides. The diastereomeric diphosphine oxides were easily separated by column chromatography with silica gel. Ruthenium catalysts containing these ligands were highly effective

  ［结构：见正文］合成了在主链上增加了手性中心的非对映体联芳基二膦配体10和11。在非对映体二膦氧化物的制备的偶联步骤中发生了底物定向的不对称合成。通过使用硅胶的柱色谱法容易地分离非对映体二膦氧化物。含有这些配体的钌催化剂在2-（6'-甲氧基-2'-萘基）丙酸和β-酮酸酯的氢化中非常有效。额外的手性中心对催化剂的对映选择性和活性有重大影响。

表征谱图