erythro-4-phenyl-3,4-dibromobutan-2-one | 6310-44-7

• 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: erythro-4-phenyl-3,4-dibromobutan-2-one
• 英文别名: 1,2-dibromo-1,3-diphenyl-1-oxopropane；(3S,4S)-3,4-dibromo-4-phenylbutan-2-one
• CAS: 6310-44-7；32147-15-2；55025-54-2
• 化学式: C₁₀H₁₀Br₂O
• 分子量: 305.997
• InChiKey: DQQMRIMUYWACAY-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090

制备方法与用途

化学性质：白色针状晶体，熔点为124-125℃。

用途：作为有机合成中间体。

生产方法：将4-苯基-3-丁烯-2-酮在四氯化碳中进行溴化处理。反应温度需控制在10-20℃之间，并避免日光照射。反应完成后，滤出产物并用甲醇重结晶，最终得到成品，产率为52-57%。

反应信息

• 作为反应物：
  描述：

  erythro-4-phenyl-3,4-dibromobutan-2-one 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.5h， 以92.1%的产率得到苄叉丙酮
  参考文献：
  名称：

  邻二卤化物光脱卤制烯烃

  摘要：

  在甲醇或三乙胺存在下辐照邻位二卤化物导致有效脱卤以再生烯烃。

  DOI：

  10.1246/cl.1983.1297
• 作为产物：
  描述：

  苄叉丙酮 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 生成 erythro-4-phenyl-3,4-dibromobutan-2-one
  参考文献：
  名称：

  Modification of chemical reactivity upon cyclodextrin encapsulation:

  摘要：

  Asymmetric bromination of chalcone and benzylideneacetone (trans-isomers) in crystalline beta-cyclodextrin complex was studied. While bromination of chalcone in the absence of beta-cyclodextrin yields erythro-dibromide, bromination of beta-cyclodextrin-chalcone complex results in the formation of a mixture of erythro- and threo-dibromides respectively in the ratio 80:20. Complexation does not induce any variation in the bromination pattern in the case of trans-benzylideneacetone. These observations have been accounted for in terms of different conformations of the enones in the beta-cyclodextrin-enone complexes. Complex formation between the substrate and cyclodextrin has been confirmed by various physical methods.

  DOI：

  10.1016/s0040-4020(01)85274-1

文献信息

• Das, Pranab Jyoti; Sarkar, Sudeshna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 6, p. 802 - 806
  作者：Das, Pranab Jyoti、Sarkar, Sudeshna

  DOI：——

  日期：——
• Pitchumani Kasi, Velusamy Ponnusamy, Sabithamala Santhamoorthy, Srinivasa+, Tetrahedron, 50 (1994) N 26, S 7903-7912
  作者：Pitchumani Kasi, Velusamy Ponnusamy, Sabithamala Santhamoorthy, Srinivasa+

  DOI：——

  日期：——
• PHOTO-DEHALOGANATION OF VICINAL DIHALIDE TO OLEFIN
  作者：Yasuji Izawa、Masaki Takeuchi、Hideo Tomioka

  DOI：10.1246/cl.1983.1297

  日期：1983.8.5

  Irradiation of vicinal dihalides in the presence of methanol or triethylamine resulted in an efficient dehalogenation to regenerate olefins.

  在甲醇或三乙胺存在下辐照邻位二卤化物导致有效脱卤以再生烯烃。
• Modification of chemical reactivity upon cyclodextrin encapsulation:
  作者：Kasi Pitchumani、Ponnusamy Velusamy、Santhamoorthy Sabithamala、Crockalingam Srinivasan

  DOI：10.1016/s0040-4020(01)85274-1

  日期：1994.1

  Asymmetric bromination of chalcone and benzylideneacetone (trans-isomers) in crystalline beta-cyclodextrin complex was studied. While bromination of chalcone in the absence of beta-cyclodextrin yields erythro-dibromide, bromination of beta-cyclodextrin-chalcone complex results in the formation of a mixture of erythro- and threo-dibromides respectively in the ratio 80:20. Complexation does not induce any variation in the bromination pattern in the case of trans-benzylideneacetone. These observations have been accounted for in terms of different conformations of the enones in the beta-cyclodextrin-enone complexes. Complex formation between the substrate and cyclodextrin has been confirmed by various physical methods.