(2R)-2-[(S)-hydroxy(phenyl)methyl]-3-methylbut-3-enoic acid | 69637-31-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R)-2-[(S)-hydroxy(phenyl)methyl]-3-methylbut-3-enoic acid
• CAS: 69637-31-6；85379-11-9；85379-12-0
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: UARFAHHROCTJNK-GHMZBOCLSA-N

物化性质

• 沸点：
  371.3±30.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-2-((S)-Acetoxy-phenyl-methyl)-3-methyl-but-3-enoic acid methyl ester 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 30.0 ℃ 、1000.0 MPa 条件下， 反应 192.0h， 生成 (2R)-2-[(S)-hydroxy(phenyl)methyl]-3-methylbut-3-enoic acid
  参考文献：
  名称：

  Cleavage of esters under nearly neutral conditions at high pressure. Chemo- and regioselective hydrolysis in organic solvents

  摘要：

  Hydrolysis of esters proceeded at room temperature under high pressures in the presence of iPr2NEt or N-methylmorpholine using CH3CN-H2O (60:1) as the solvent. This very mild procedure enables the smooth hydrolysis of biologically important compounds such as amino esters, aliphatic unsaturated fatty esters, and beta-hydroxy esters; no racemization, no isomerization, and no side reactions take place.

  DOI：

  10.1021/jo00020a001

文献信息

• Exclusive <i>α</i>-Coupling in the Aldol Reaction of Unsaturated Trimethylsilyl Esters: An Efficient and Practical Direct Synthesis of Unsaturated <i>β</i>-Hydroxy Acids
  作者：Moncef Bellassoued、Jérôme Grugier、Nathalie Lensen、Audrey Catheline

  DOI：10.1021/jo020128u

  日期：2002.8.1

  give exclusively the alpha-condensation products in excellent yields. The unsaturated beta-hydroxy acids thus obtained were directly identified, and the usual conversion into their methyl esters with diazomethane was not necessary. Unsaturated ketones underwent Michael reaction through alpha-addition leading to the unsaturated 5-oxo acids.

  丁烯酸三甲基甲硅烷基酯和丁烯酸3-甲基丁酯的烯醇锂与醛和饱和或芳香族酮在-70℃下反应，以优异的产率仅得到α缩合产物。由此获得的不饱和β-羟基酸被直接鉴定，并且不需要用重氮甲烷通常转化为它们的甲酯。不饱和酮通过α加成反应发生迈克尔反应，从而导致不饱和5-氧代酸。
• Cleavage of esters under nearly neutral conditions at high pressure. Chemo- and regioselective hydrolysis in organic solvents
  作者：Yoshinori Yamamoto、Toshiaki Furuta、Jiro Matsuo、Tetsuro Kurata

  DOI：10.1021/jo00020a001

  日期：1991.9

  Hydrolysis of esters proceeded at room temperature under high pressures in the presence of iPr2NEt or N-methylmorpholine using CH3CN-H2O (60:1) as the solvent. This very mild procedure enables the smooth hydrolysis of biologically important compounds such as amino esters, aliphatic unsaturated fatty esters, and beta-hydroxy esters; no racemization, no isomerization, and no side reactions take place.