3-oxo-2-(1-phenyl-ethyl)-butyric acid ethyl ester | 26728-49-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-oxo-2-(1-phenyl-ethyl)-butyric acid ethyl ester
• 英文别名: ethyl 3-oxo-2-(1-phenylethyl)butanoate；ethyl 2-acetyl-3-phenylbutanoate
• CAS: 26728-49-4
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: MNNWWCGUHJRQRB-UHFFFAOYSA-N

物化性质

• 沸点：
  129-131 °C(Press: 5 Torr)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-2-(1-phenyl-ethyl)-butyric acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 以63%的产率得到4-苯基戊烷-2-酮
  参考文献：
  名称：

  Cookson, Richard C.; Sadler, David E.; Salisbury, Kingsley, Journal of the Chemical Society. Perkin transactions II, 1981, p. 774 - 782

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯亚甲基乙酰乙酸乙酯 、 三甲基镓 以 乙醚 为溶剂， 以87%的产率得到3-oxo-2-(1-phenyl-ethyl)-butyric acid ethyl ester
  参考文献：
  名称：

  Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents

  摘要：

  Triorganogallium and -indium reagents reacted with alpha,beta unsaturated nitrile and carbonyl compounds to give 1.4-addition products regioselectively. The reaction of allylgallium and allylindium sesquihalides with alpha,beta-unsaturatedcarbonyl compounds proceeded in a 1,2-addition mode, whereas a 1,4-addition took place with alpha,beta-unsaturated nitriles. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00179-3

文献信息

• A simple and efficient FeCl3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions
  作者：Umasish Jana、Srijit Biswas、Sukhendu Maiti

  DOI：10.1016/j.tetlet.2007.04.017

  日期：2007.6

  A highly efficient FeCl3-catalyzed alkylation of various active methylene compounds with various benzylic or allylic alcohols under mild conditions has been developed. The reaction was carried out in the presence of a catalytic amount of anhydrous FeCl3 (10 mol %) under reflux in methylene chloride. High to excellent yields were obtained.

  已经开发了在温和条件下用各种苄基或烯丙基醇高效催化FeCl 3催化的各种活性亚甲基化合物的烷基化反应。该反应在催化量的无水FeCl 3（10mol％）的存在下在二氯甲烷中回流下进行。获得了高到优异的产率。
• Amberlyst-15® in ionic liquid: an efficient and recyclable reagent for the benzylation and hydroalkylation of β-dicarbonyl compounds
  作者：Ziyauddin S. Qureshi、Krishna M. Deshmukh、Pawan J. Tambade、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2009.11.122

  日期：2010.1

  Benzylation and hydroalkylation of 1,3-dicarbonyl compounds using Amberlyst-15 immobilized in ionic liquid [Bmim][PF6] as an efficient reusable reagent was studied. The reagent was compared with other solid acid reagents along with role of the ionic liquid. The effect of various reaction parameters like type of reagent, solvent, substrate molar ratio, reaction time, and temperature were studied. Present

  以固定在离子液体[Bmim] [PF 6 ]中的Amberlyst-15为有效的可重复使用试剂，研究了1,3-二羰基化合物的苯甲酸酯化和加氢烷基化。将该试剂与其他固体酸试剂以及离子液体的作用进行了比较。研究了试剂类型，溶剂，底物摩尔比，反应时间和温度等各种反应参数的影响。由于易于处理试剂，简单的后处理程序，经济和环境友好的方法，因此本方案是有利的。获得的产品具有良好的优良收率，并适用于多种基材。
• Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(<scp>iii</scp>) compound
  作者：Mohan Chandra Sau、Smita Mandal、Manish Bhattacharjee

  DOI：10.1039/d0ra09778k

  日期：——

  Monoallylation and monoalkylation of diketones and β-keto esters with allylic and benzylic alcohols catalysed by [Cp*Co(CH3CN)3][SbF6]2 (I) are reported. The method does not require any additive and affords regioselective products. The mechanistic investigations were done by in situ 1H NMR spectroscopy as well as control experiments. It has been shown that reactions proceed via η3-allyl complex formation or

  报道了[Cp*Co(CH 3 CN) 3 ][SbF 6 ] 2 ( I )催化的二酮和β-酮​​酯与烯丙醇和苄醇的单烯丙基化和单烷基化。该方法不需要任何添加剂并提供区域选择性产物。通过原位1 H NMR 光谱以及对照实验进行了机理研究。已表明反应通过形成 η 3 -烯丙基络合物或烯丙基醚中间体进行。烷基化仅通过醚中间体发生。所得烯丙基化和烷基化产物已用于合成十一种新的三取代吡唑和一种吡唑啉酮。
• Solvent-Free Alkylation of 1,3-Dicarbonyl Compounds with Benzylic, Propargylic and Allylic Alcohols Catalyzed by La(NO3)3·6H2O
  作者：Madala Subramanyam、Koya Prabhakara Rao、Ravi Varala、Mandava V. Basaveswara Rao

  DOI：10.14233/ajchem.2016.19621

  日期：——

  An efficient and solvent free method for benzylation, propargylation and allylation of 1,3-dicarbonyl compounds with alcohols has been developed by using La(NO3)3·6H2O as water tolerable catalyst. The reaction was shown to proceed smoothly for various 1,3-dicarbonyl compounds with benzylic, propargylic and allylic alcohols including 10 allylic alcohols, without any solvent, providing a clean access to the desired products in short reaction times with good to excellent yields and high selectivity.

  一种高效且无溶剂的方法已被开发，用于1,3-二羧基化合物与醇的苄基化、丙炔基化和烯丙基化，采用La(NO3)3·6H2O作为耐水催化剂。该反应在没有任何溶剂的情况下，对多种1,3-二羧基化合物与苄醇、丙炔醇及烯丙醇（包括10种烯丙醇）进行顺利进行，提供了干净的反应途径，具有短的反应时间、良好至优秀的产率和高选择性。
• Base-free benzylation of 1,3-dicarbonyl compounds using sulfamic acid supported on silica by linker: a combined experimental and theoretical approach
  作者：Morteza Karimzadeh、Hamed Saberi Asl、Hajar Hashemi、Dariush Saberi、Khodabakhsh Niknam

  DOI：10.1007/s00706-018-2284-x

  日期：2018.12

  AbstractSulfamic acid stabilized on the surface of silica by the n-propyl organic group linker which is named silica-bonded N-propylsulfamic acid was applied as an efficient heterogeneous catalyst with good recyclability and reusability for direct benzylation of 1,3-dicarbonyl compounds using secondary aromatic alcohols or styrenes as alkylating agents in high yields and short reaction times. All the

  摘要通过正丙基有机基团连接剂稳定在二氧化硅表面的氨基磺酸被称为二氧化硅键合的N-丙基氨基磺酸，是一种高效的多相催化剂，具有良好的可回收性和可重复使用性，可通过二次使用直接将1,3-二羰基化合物苄基化芳烃或苯乙烯作为烷基化剂的收率高，反应时间短。所有反应在空气气氛下在硝基甲烷中作为溶剂进行。该催化剂表现出六次可重复使用的特性，而活性没有明显损失。 图形概要