trans-(2R,3S)-epoxy-1-(4-bromophenyl)-3-(4-chlorophenyl) propan-1-one | 27547-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-(2R,3S)-epoxy-1-(4-bromophenyl)-3-(4-chlorophenyl) propan-1-one
• 英文别名: trans-(2R,3S)-epoxy-1-(4-bromophenyl)-3-(4-chlorophenyl)proan-1-one；(4-bromophenyl)-[(2R,3S)-3-(4-chlorophenyl)oxiran-2-yl]methanone
• CAS: 27547-11-1；32157-72-5
• 化学式: C₁₅H₁₀BrClO₂
• 分子量: 337.6
• InChiKey: TYYLAGRJMVTAEC-GJZGRUSLSA-N

物化性质

• 沸点：
  459.2±45.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-(2R,3S)-epoxy-1-(4-bromophenyl)-3-(4-chlorophenyl) propan-1-one 在 metal halide 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  SnCl₄ or TiCl₄: highly efficient catalysts for the detetrahydropyranylation and demethoxymethylation of phenolic ethers and sequential one-pot asymmetric synthesis of 3-aryl-2-hydroxy-2,3-dihydroindan-1-ones from chalcone epoxides

  摘要：

  在温和的反应条件下，SnCl4 或 TiCl4 催化剂可快速高效地实现酚醚的脱四氢吡喃化和脱甲氧基甲基化，以及查尔酮环氧化物的单锅顺序分子内 Friedel-Crafts 烷基化反应。

  DOI：

  10.1039/c5ra10499h
• 作为产物：
  描述：

  1-(4-溴苯基)-3-(4-氯苯基)-2-丙烯-1-酮 在 C₅₈H₆₄N₄O₄S⁽²⁺⁾*2Br^(1-) 、 双氧水 、 caesium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 4.5h， 以97%的产率得到trans-(2R,3S)-epoxy-1-(4-bromophenyl)-3-(4-chlorophenyl) propan-1-one
  参考文献：
  名称：

  A new class of bifunctional chiral phase transfer catalysts for highly enantioselective asymmetric epoxidation of α,β-unsaturated ketones at ambient temperature

  摘要：

  A new type of bis-quaternary ammonium bromide as chiral multifunctional phase transfer catalysts derived from readily available inexpensive cinchona alkaloids has been developed and evaluated for the enantioselective asymmetric epoxidation of various chalcones in the presence of lower concentrations of various oxidants, bases, solvents and ambient temperature conditions. Under optimized reaction conditions, highest chemical yields of up to 98% along with the excellent enantioselectivities of about 99% were obtained by using the cinchona based chiral multifunctional phase transfer catalysts. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.08.016

文献信息

• Ultrasonic assisted dimeric cinchona based chiral phase transfer catalysts for highly enanatioselective synthesis of epoxidation of α,β-unsaturated ketones
  作者：Jayaraman Sivamani、Veeramanoharan Ashokkumar、Velu Sadhasivam、Kumaraguru Duraimurugan、Ayyanar Siva

  DOI：10.1039/c4ra10952j

  日期：——

  New types of bis-quaternary ammonium bromide as chiral multisite phase transfer catalysts derived from cinchona alkaloids have been developed and evaluated for the enantioselective epoxidation of chalcones in the presence of lower concentrations of various oxidants, bases and ultrasonic irradiation conditions.

  新型的双季铵溴化物作为手性多位相转移催化剂，由金鸡纳生物碱衍生而来，已经被开发并用于在低浓度各种氧化剂、碱和超声辐射条件下对香豆素的对映选择性环氧化进行评估。
• A new class of bifunctional chiral phase transfer catalysts for highly enantioselective asymmetric epoxidation of α,β-unsaturated ketones at ambient temperature
  作者：Veeramanoharan Ashokkumar、Rajendiran Balasaravanan、Velu Sadhasivam、Seenisultanmaideen Mehtob Jenofar、Ayyanar Siva

  DOI：10.1016/j.molcata.2015.08.016

  日期：2015.12

  A new type of bis-quaternary ammonium bromide as chiral multifunctional phase transfer catalysts derived from readily available inexpensive cinchona alkaloids has been developed and evaluated for the enantioselective asymmetric epoxidation of various chalcones in the presence of lower concentrations of various oxidants, bases, solvents and ambient temperature conditions. Under optimized reaction conditions, highest chemical yields of up to 98% along with the excellent enantioselectivities of about 99% were obtained by using the cinchona based chiral multifunctional phase transfer catalysts. (C) 2015 Elsevier B.V. All rights reserved.
• SnCl₄ or TiCl₄: highly efficient catalysts for the detetrahydropyranylation and demethoxymethylation of phenolic ethers and sequential one-pot asymmetric synthesis of 3-aryl-2-hydroxy-2,3-dihydroindan-1-ones from chalcone epoxides
  作者：Naseem Ahmed、Gulab Khushalrao Pathe、Sohan Jheeta

  DOI：10.1039/c5ra10499h

  日期：——

  SnCl₄ or TiCl₄ catalysts provide a rapid and efficient detetrahydropyranylation and demethoxymethylation of phenolic ethers and a sequential one-pot intramolecular Friedel–Crafts alkylation of chalcone epoxides under mild reaction conditions.

  在温和的反应条件下，SnCl4 或 TiCl4 催化剂可快速高效地实现酚醚的脱四氢吡喃化和脱甲氧基甲基化，以及查尔酮环氧化物的单锅顺序分子内 Friedel-Crafts 烷基化反应。