Methyl 2-(phenylhydroxymethyl)-3-methyl-3-butenoate | 72853-34-0

• 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: Methyl 2-(phenylhydroxymethyl)-3-methyl-3-butenoate
• 英文别名: methyl (2R)-2-[(S)-hydroxy(phenyl)methyl]-3-methylbut-3-enoate
• CAS: 72853-34-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: SOSOLLSNITWEHD-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-(phenylhydroxymethyl)-3-methyl-3-butenoate 在 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 30.0 ℃ 、999.99 MPa 条件下， 反应 96.0h， 以91%的产率得到(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
• 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 为溶剂， 30.0 ℃ 、999.99 MPa 条件下， 反应 96.0h， 以85%的产率得到Methyl 2-(phenylhydroxymethyl)-3-methyl-3-butenoate
  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

• Stereoselective synthesis of substituted oxetanes
  作者：Paul Galatsis、Daniel J. Parks

  DOI：10.1016/s0040-4039(00)73448-4

  日期：1994.9

  The stereospecific synthesis of substituted oxetanes was shown to be feasible through the use of a deconjugative aldol-cyclization sequence.
• A general synthesis of 5,6-dihydro-.alpha.-pyrones
  作者：R. W. Dugger、Clayton H. Heathcock

  DOI：10.1021/jo01295a002

  日期：1980.3
• 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.