2-Hydroxy-2-hydroxymethyl-3-phenyl-propionic acid methyl ester | 187090-97-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-Hydroxy-2-hydroxymethyl-3-phenyl-propionic acid methyl ester
• CAS: 187090-97-7
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: OOXFCYRMEUXNGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-2-hydroxymethyl-3-phenyl-propionic acid methyl ester 在 4-二甲氨基吡啶 、 二乙胺基三氟化硫 作用下， 以 三乙胺 为溶剂， 反应 48.0h， 生成 2-Benzyl-2-fluoro-3-trityloxy-propionic acid methyl ester
  参考文献：
  名称：

  The nature of interaction between the carboxylate of substrates and the guanidinium moiety of Arg-145 in carboxypeptidase A probed by inhibitors of the enzyme

  摘要：

  Replacement of the alpha-proton of 2-benzyl-3-hydoroxypropanoic acid a competitive inhibitor of carboxypeptidase A with a fluoro group brought about a 2-fold increase in K-i value (0.61 mM --> 1.19 mM), while pK(a) value decreased by 1.4 units (4.36 --> 2.95), suggesting that the carboxylate of the inhibitor and that of substrates as well are hydrogen bonded to the guanidinium moiety of Arg-145 of the enzyme. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00541-0
• 作为产物：
  描述：

  2-苄基丙烯酸甲酯 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 36.0h， 以91%的产率得到2-Hydroxy-2-hydroxymethyl-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  The nature of interaction between the carboxylate of substrates and the guanidinium moiety of Arg-145 in carboxypeptidase A probed by inhibitors of the enzyme

  摘要：

  Replacement of the alpha-proton of 2-benzyl-3-hydoroxypropanoic acid a competitive inhibitor of carboxypeptidase A with a fluoro group brought about a 2-fold increase in K-i value (0.61 mM --> 1.19 mM), while pK(a) value decreased by 1.4 units (4.36 --> 2.95), suggesting that the carboxylate of the inhibitor and that of substrates as well are hydrogen bonded to the guanidinium moiety of Arg-145 of the enzyme. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00541-0

文献信息

• Tunable<i>Cinchona</i>-Based Thioureas-Catalysed Asymmetric Epoxidation to Synthetically Important Glycidic Ester Derivatives
  作者：Sara Meninno、Luca Zullo、Jacob Overgaard、Alessandra Lattanzi

  DOI：10.1002/adsc.201700146

  日期：2017.3.20

  A novel class of synthetically important glycidic esters has been obtained via an asymmetric epoxidation of trans‐α‐cyano‐α,β‐unsaturated esters catalysed by a multifunctional Cinchona alkaloid‐derived thiourea/tert‐butyl hydroperoxide (TBHP) system. The glycidic esters, isolated in excellent yield with complete trans‐diastereocontrol and high enantioselectivity, proved to be versatile building blocks

  已经获得了一种新的类合成重要的缩水甘油酯的通过的不对称环氧化反式-α氰基α，通过多官能催化β -不饱和酯金鸡纳生物碱类硫脲/叔丁基过氧化氢（TBHP）系统。缩水甘油酯以极高的收率分离，具有完全的反式-非对映异构控制和高对映选择性，被证明是通向具有四级立体中心的具有挑战性的小目标的通用构建基块。
• The nature of interaction between the carboxylate of substrates and the guanidinium moiety of Arg-145 in carboxypeptidase A probed by inhibitors of the enzyme
  作者：Dong H. Kim、Jeong- il Park

  DOI：10.1016/s0960-894x(96)00541-0

  日期：1996.12

  Replacement of the alpha-proton of 2-benzyl-3-hydoroxypropanoic acid a competitive inhibitor of carboxypeptidase A with a fluoro group brought about a 2-fold increase in K-i value (0.61 mM --> 1.19 mM), while pK(a) value decreased by 1.4 units (4.36 --> 2.95), suggesting that the carboxylate of the inhibitor and that of substrates as well are hydrogen bonded to the guanidinium moiety of Arg-145 of the enzyme. Copyright (C) 1996 Elsevier Science Ltd