ethyl 2-bromo-3-hydroxy-2-methyl-3-phenylpropanoate | 153645-09-1

• 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: ethyl 2-bromo-3-hydroxy-2-methyl-3-phenylpropanoate
• 英文别名: Ethyl 2-bromo-3-hydroxy-2-methyl-3-phenylpropanoate
• CAS: 153645-09-1
• 化学式: C₁₂H₁₅BrO₃
• 分子量: 287.153
• InChiKey: BOQNABDKBHDWDE-UHFFFAOYSA-N

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：
  0.42
• 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：

  ethyl 2-bromo-3-hydroxy-2-methyl-3-phenylpropanoate 在 三正丁基氢锡 、 六正丁基二锡 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 生成 Ethyl 2-methyl-3-fluoro-3-phenylpropionate
  参考文献：
  名称：

  极性取代基对烯醇式自由基构象和立体化学的影响

  摘要：

  ESR测量和AM1计算表明，由于烯丙基应变效应，酯取代的基团2和6更偏爱构象A。但是，取代基X和CO 2 Et In 2和6之间的偶极排斥力对自由基2和6的构象和立体选择性具有显着影响。

  DOI：

  10.1016/s0040-4039(00)73805-6
• 作为产物：
  描述：

  ethyl 2-methylcinnamate 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 水 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以76%的产率得到ethyl 2-bromo-3-hydroxy-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates

  摘要：

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.

  DOI：

  10.1021/jo00042a029

文献信息

• The effect of polar substituents on the conformation and stereochemistry of enolate radicals
  作者：B. Giese、W. Damm、F. Wetterich、H.-G. Zeitz、J. Rancourt、Y. Guindon

  DOI：10.1016/s0040-4039(00)73805-6

  日期：1993.9

  ESR measurements and AM1 calculations show that ester substituted radicals 2 and 6 prefer conformation A as a result of allylic strain effects. But dipolar repulsion between substituents X and CO2Et In 2 and 6 has a pronounced effect on the conformation and the stereoselectivity of radicals 2 and 6.

  ESR测量和AM1计算表明，由于烯丙基应变效应，酯取代的基团2和6更偏爱构象A。但是，取代基X和CO 2 Et In 2和6之间的偶极排斥力对自由基2和6的构象和立体选择性具有显着影响。
• Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates
  作者：David J. Hart、Ramanarayanan Krishnamurthy

  DOI：10.1021/jo00042a029

  日期：1992.7

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.