methyl (2S*,3R*)-2-bromo-3-methoxy-3-phenylpropanoate | 52742-05-9

• 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: methyl (2S*,3R*)-2-bromo-3-methoxy-3-phenylpropanoate
• 英文别名: threo-2-Brom-3-methoxy-3-phenyl-propionsaeure-methylester；methyl (2R,3S)-2-bromo-3-methoxy-3-phenylpropanoate
• CAS: 52742-05-9；52781-50-7；60456-13-5；64856-34-4；65091-58-9
• 化学式: C₁₁H₁₃BrO₃
• 分子量: 273.126
• InChiKey: KOMNPVFCQMJEHR-ZJUUUORDSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  327.3±37.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 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：

  methyl (2S*,3R*)-2-bromo-3-methoxy-3-phenylpropanoate 、 烯丙基三甲基硅烷 在 三乙基硼 、 magnesium bromide 作用下， 生成 methyl (2S*,3R*)-2--3-methoxy-3-phenylpropanoate
  参考文献：
  名称：

  Stereoselective Radical Carbon−Carbon Bond Forming Reactions of β-Alkoxy Esters:  Atom and Group Transfer Allylations under Bidentate Chelation Controlled Conditions

  摘要：

  The radical allylation of a series of beta-alkoxy esters using allyltrimethylsilane in the presence of MgBr2 . OEt(2) is described. Under bidentate chelation-controlled conditions, allyltrimethylsilane rivals allyltributyltin in efficiency and is a superior reagent from ecological and practical perspectives. The reactions work with iodides and bromides as well as phenylselenides. The isolation of gamma-phenylseleno intermediates indicates that the reaction proceeds by an atom transfer process. These reactions require initiation with Et(3)B and can be inhibited by galvinoxyl, m- and p-dinitrobenzene indicating that this atom transfer sequence involves the intermediacy of radicals.

  DOI：

  10.1021/ja9541241
• 作为产物：
  描述：

  Methyl(R,R)-2-bromo-3-methoxy-3-phenylpropanoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl (2S*,3R*)-2-bromo-3-methoxy-3-phenylpropanoate
  参考文献：
  名称：

  Cabaleiro, Mercedes C.; Garay, Raul O., Journal of the Chemical Society. Perkin transactions II, 1986, p. 1091 - 1096

  摘要：

  DOI：

文献信息

• Vishwakarma,L.C.; Walia,J.S., Journal of the Indian Chemical Society, 1976, vol. 53, p. 156 - 162
  作者：Vishwakarma,L.C.、Walia,J.S.

  DOI：——

  日期：——
• Stereoselective Radical Carbon−Carbon Bond Forming Reactions of β-Alkoxy Esters:  Atom and Group Transfer Allylations under Bidentate Chelation Controlled Conditions
  作者：Y. Guindon、B. Guérin、C. Chabot、W. Ogilvie

  DOI：10.1021/ja9541241

  日期：1996.1.1

  The radical allylation of a series of beta-alkoxy esters using allyltrimethylsilane in the presence of MgBr2 . OEt(2) is described. Under bidentate chelation-controlled conditions, allyltrimethylsilane rivals allyltributyltin in efficiency and is a superior reagent from ecological and practical perspectives. The reactions work with iodides and bromides as well as phenylselenides. The isolation of gamma-phenylseleno intermediates indicates that the reaction proceeds by an atom transfer process. These reactions require initiation with Et(3)B and can be inhibited by galvinoxyl, m- and p-dinitrobenzene indicating that this atom transfer sequence involves the intermediacy of radicals.
• Cabaleiro, Mercedes C.; Garay, Raul O., Journal of the Chemical Society. Perkin transactions II, 1986, p. 1091 - 1096
  作者：Cabaleiro, Mercedes C.、Garay, Raul O.

  DOI：——

  日期：——