Benzoic acid (S)-3-acetoxy-2-methyl-propyl ester | 141885-92-9

• 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: Benzoic acid (S)-3-acetoxy-2-methyl-propyl ester
• CAS: 141885-92-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: VQGOPOCXQHUFMX-JTQLQIEISA-N

物化性质

• 沸点：
  336.6±25.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 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：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯甲酸乙烯酯 在 diethylzinc 2,6-di-(S)-((((4-Ph-Ph)2C(OH))C₄H₇N)CH₂)-4-MeC₆H₂OH 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 44.0h， 生成 Benzoic acid (S)-3-acetoxy-2-methyl-propyl ester
  参考文献：
  名称：

  Desymmetrization of Meso 1,3- and 1,4-Diols with a Dinuclear Zinc Asymmetric Catalyst

  摘要：

  A dinuclear asymmetric zinc catalyst generated by mixing a 2:1 ratio of diethylzinc and 2,6-bis[5-2-diarylhydroxy methyl-1-pyrrolidinyl]-4-methylphenol has been contrasted with enzymes for the desymmetrization of some meso diols. The best ligand has a p-biphenylyl group as the aromatic substituent defining the chiral space. A series of 2-substituted propanediols were examined. The best acyl transfer agent proved to be vinyl benzoate. Diacylation normally did not occur. The phenyl substituted substrate gave 91-95% ee which compares favorably with the best ee of 92% reported for an enzymatic desymmetrization. The methyl substituted substrate gave significantly better results with the dinuclear zinc catalyst (89% yield, 82% ee) as compared to the best enzymatic esterification (70% yield, 60% ee). One case of a 1,4-diol, cis-1,2-bis(hydroxymethyl) cyclohexane, also gave much better results with the dinuclear zinc catalysts (93% yield, 91% ee) as compared to the reported enzymatic process (44% yield, 7% ee). A model to rationalize the results is presented.

  DOI：

  10.1021/ja029708z

文献信息

• Enantioselective transesterification of 2-methyl-1,3-propanediol derivatives catalyzed by Pseudomonas fluorescens lipase in an organic solvent
  作者：Paride Grisenti、Patrizia Ferraboschi、Ada Manzocchi、Enzo Santaniello

  DOI：10.1016/s0040-4020(01)92273-2

  日期：1992.1

  The irreversible transesterification of racemic 2-methyl-1,3-propanediol derivatives, the monoethers, 3a, 3b, 5a, and the monobenzoate 5b, with vinyl acetate catalyzed by Pseudomonas fluorescens lipase in chloroform affords enantiomerically pure chiral synthons.

  外消旋的2-甲基-1,3-丙二醇衍生物，单醚3a，3b，5a和单苯甲酸酯5b与氯乙烯假单胞菌脂肪酶催化的乙酸乙烯酯的不可逆酯交换反应提供对映体纯的手性合成子。
• Desymmetrization of Meso 1,3- and 1,4-Diols with a Dinuclear Zinc Asymmetric Catalyst
  作者：Barry M. Trost、Takashi Mino

  DOI：10.1021/ja029708z

  日期：2003.3.1

  A dinuclear asymmetric zinc catalyst generated by mixing a 2:1 ratio of diethylzinc and 2,6-bis[5-2-diarylhydroxy methyl-1-pyrrolidinyl]-4-methylphenol has been contrasted with enzymes for the desymmetrization of some meso diols. The best ligand has a p-biphenylyl group as the aromatic substituent defining the chiral space. A series of 2-substituted propanediols were examined. The best acyl transfer agent proved to be vinyl benzoate. Diacylation normally did not occur. The phenyl substituted substrate gave 91-95% ee which compares favorably with the best ee of 92% reported for an enzymatic desymmetrization. The methyl substituted substrate gave significantly better results with the dinuclear zinc catalyst (89% yield, 82% ee) as compared to the best enzymatic esterification (70% yield, 60% ee). One case of a 1,4-diol, cis-1,2-bis(hydroxymethyl) cyclohexane, also gave much better results with the dinuclear zinc catalysts (93% yield, 91% ee) as compared to the reported enzymatic process (44% yield, 7% ee). A model to rationalize the results is presented.