[(2R)-1-bromo-3-phenoxypropan-2-yl] acetate | 140630-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2R)-1-bromo-3-phenoxypropan-2-yl] acetate
• CAS: 140630-40-6
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 273.126
• InChiKey: MDPQERSQALETFT-NSHDSACASA-N

物化性质

• 沸点：
  339.0±27.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R)-1-bromo-3-phenoxypropan-2-yl] acetate 在 potassium tert-butylate 、 氨 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2S)-(-)-1-氨基-3-苯氧基-2-丙醇
  参考文献：
  名称：

  Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion

  摘要：

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.

  DOI：

  10.1016/s0957-4166(00)80191-3
• 作为产物：
  描述：

  1-溴-3-苯氧基丙烷-2-基乙酸酯 生成 [(2R)-1-bromo-3-phenoxypropan-2-yl] acetate
  参考文献：
  名称：

  Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion

  摘要：

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.

  DOI：

  10.1016/s0957-4166(00)80191-3

文献信息

• A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides
  作者：Hartmuth C. Kolb、K.Barry Sharpless

  DOI：10.1016/s0040-4020(01)88349-6

  日期：1992.11

  of vicinal diols into epoxides via halohydrin ester intermediates has been developed. This method tolerates a wide range of functionality including acid sensitive functional groups. The transformation proceeds via a, usually highly regioselective, nucleophilic opening of a cyclic acetoxonium intermediate, generated from a cyclic orthoacetate and Me3SiCl, acetyl bromide or acetyl chloride/NaI to form

  已经开发出一种简单的“一锅法”程序，用于通过卤代醇酯中间体将邻位二醇转化为环氧化物。该方法可耐受包括酸敏感性官能团在内的多种官能团。变换进行经由环状acetoxonium中间的一个，通常是高度选择性，亲核开口，由环状原乙酸酯和Me产生3用SiCl，乙酰溴或乙酰氯/ NaI分别形成1-乙酰氧基-2-氯化物，1-乙酰氧基-2-溴化物或1-乙酰氧基-2-碘化物中间体。即使有苄基底物也不会发生差向异构。随后的碱介导的甲醇分解以优异的总收率提供了环氧化物。从3- [2-（8-苯基辛基）苯基]丙酸甲酯的高度对映选择性顺式-二羟基化开始，该方法的应用导致白三烯拮抗剂SKF 104353的有效形式合成。
• Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion
  作者：Ulrich Ader、Manfred.P. Schneider

  DOI：10.1016/s0957-4166(00)80191-3

  日期：1992.1

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.