(Z)-phenyl 2-(bromomethyl)-3-(4-chlorophenyl)acrylate | 1351533-80-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-phenyl 2-(bromomethyl)-3-(4-chlorophenyl)acrylate
• 英文别名: phenyl (Z)-2-(bromomethyl)-3-(4-chlorophenyl)prop-2-enoate
• CAS: 1351533-80-6
• 化学式: C₁₆H₁₂BrClO₂
• 分子量: 351.627
• InChiKey: XWDFSGMYVRTHPI-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-phenyl 2-(bromomethyl)-3-(4-chlorophenyl)acrylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 (S)-2-(7-(triphenylsilyloxy)tridecan-7-yl)pyrrolidine 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 63.5h， 生成 (4R,5S)-phenyl 5-(4-chlorophenyl)-4-(diethoxymethyl)-cyclopent-1-enecarboxylate
  参考文献：
  名称：

  Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates

  摘要：

  The catalytic direct alpha-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to alpha-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.

  DOI：

  10.1021/jo202073n
• 作为产物：
  描述：

  丙烯酸苯酯 在 三乙烯二胺 、 Na⁽¹⁺⁾*HSO₄^(1-)*SiO₂ = NaHSO₄*SiO₂ 、 lithium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 (Z)-phenyl 2-(bromomethyl)-3-(4-chlorophenyl)acrylate
  参考文献：
  名称：

  Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates

  摘要：

  The catalytic direct alpha-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to alpha-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.

  DOI：

  10.1021/jo202073n

文献信息

• Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates
  作者：Jacqueline Jiménez、Aitor Landa、Aitziber Lizarraga、Miguel Maestro、Antonia Mielgo、Mikel Oiarbide、Irene Velilla、Claudio Palomo

  DOI：10.1021/jo202073n

  日期：2012.1.6

  The catalytic direct alpha-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to alpha-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.