2-苄基-2-甲基-3-氧代丁酸甲酯 | 135508-23-5

• 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: 2-苄基-2-甲基-3-氧代丁酸甲酯
• 英文名称: methyl 2-benzyl-2-methyl-3-oxobutanoate
• 英文别名: 2-benzyl-2-methyl-acetoacetic acid methyl ester；2-Benzyl-2-methyl-acetessigsaeure-methylester
• CAS: 135508-23-5
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: LYLMMRGRDROBLC-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  302.5±22.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-苄基-2-甲基-3-氧代丁酸甲酯 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 水 为溶剂， 反应 49.0h， 生成 methyl 2-benzyl-2-methyl-3-chlorobutanoate
  参考文献：
  名称：

  Syntheses and Kinetic Evaluation of Racemic and Optically Active 2-Benzyl-2-methyl-3,4-epoxybutanoic Acids as Irreversible Inactivators for Carboxypeptidase A

  摘要：

  Racemic and optically active 2-benzyl-2-methyl-3,4-epoxybutanoic acids were synthesized and evaluated as inactivators for carboxypeptidase A. a representative zinc-containing proteolytic enzyme. Only the threo-form of the inactivator is effective and its potency in terms of k(inact)/K-I value is lower by 42-fold compared with 2-benzyl-3,4-epoxybutanoic acid, indicating that the alpha-methyl group affects adversely in the inactivation contrary to the expectation that it would enhance the inactivation activity of the inhibitor through additional interactions of the methyl group with a small cavity (alpha-methyl hole) present next to the S-1' hydrophobic pocket. Of the enantiomeric pair, the inactivator having the (2S,3R)-configuration is more potent than its enantiomer by 44-fold. The observed kinetic results may be rationalized on the basis that the methyl group in the inactivator having the (2R,3S)configuration experiences the van der Waals repulsive interactions with the bottom of the active site crevice in binding to CPA, casting a doubt on the presence of the so-called alpha-methyl hole at the active site of carboxypeptidase A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00340-6
• 作为产物：
  描述：

  2-甲基-3-氧代丁酸甲酯 在 甲醇 、 sodium methylate 作用下， 生成 2-苄基-2-甲基-3-氧代丁酸甲酯
  参考文献：
  名称：

  Synthesis of isomer-free benzyl methyl acetoacetic methyl ester

  摘要：

  公开号：

  US02413493A1

文献信息

• Dealkoxycarbonylations of Gem Diesters and β-Ketoesters via an Enzyme Catalyzed Hydrolysis
  作者：M. Ahmar、R. Bolch、M. Bortolussi

  DOI：10.1080/00397919108019796

  日期：1991.4

  Abstract A new method for the dealkoxycarbonylation of malonate esters and β-ketoesters, involving an enzyme catalyzed hydrolysis followed by a high temperature Kugelroher distillation, is described.

  摘要 描述了一种丙二酸酯和 β-酮酯脱烷氧基羰基化的新方法，包括酶催化水解和高温 Kugelroher 蒸馏。
• AHMAR, M.;BLOCH, R.;BORTOLUSSI, M., SYNTH. COMMUN., 21,(1991) N-9, C. 1071-1074
  作者：AHMAR, M.、BLOCH, R.、BORTOLUSSI, M.

  DOI：——

  日期：——