(Z)-2-chloro-3-(4-methylphenyl)acrylaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (Z)-2-chloro-3-(4-methylphenyl)acrylaldehyde
• 英文别名: (Z)-2-chloro-3-(4-methylphenyl)prop-2-enal
• 化学式: C₁₀H₉ClO
• 分子量: 180.634
• InChiKey: NZCZYPASJFKYGL-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,2,2-三氯-1-乙氧基乙醇 、 对甲基苯甲醛 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以91%的产率得到(Z)-2-chloro-3-(4-methylphenyl)acrylaldehyde
  参考文献：
  名称：

  Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin

  摘要：

  The CrCl(2)-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-alpha-chloro- and (Z)-alpha-bromo-alpha,beta-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.026

文献信息

• A New Synthetic Approach to α-Chlorocinnamaldehydes
  作者：Valentine Nenajdenko、Alexander Reznichenko、Olesya Lenkova、Alexey Shastin、Elizabeth Balenkova

  DOI：10.1055/s-2004-837303

  日期：——

  A new simple and efficient transformation of aromatic aldehydes into α-chlorocinnamaldehydes is described. Catalytic olefination reaction of hydrazones of aromatic aldehydes with 2-trichloromethyl-1,3-dioxolane gives ethylene acetals of target alkenes in moderate to good yields. The reaction proceeds stereoselectively to form preferably Z-isomers.

  报道了一种将芳香醛转化为α-氯肉桂醛的新型简单高效转化方法。催化炔丙化反应，利用芳香醛的踪与2-三氯甲基-1,3-二恶烷反应，以中等至良好产率得到目标烯烃的乙烯缩醛。该反应立体选择性地进行，优先形成Z-异构体。
• Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin
  作者：Deb K. Barma、Biao Lu、Rachid Baati、Charles Mioskowski、J.R. Falck

  DOI：10.1016/j.tetlet.2008.05.026

  日期：2008.7

  The CrCl(2)-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-alpha-chloro- and (Z)-alpha-bromo-alpha,beta-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis. (C) 2008 Elsevier Ltd. All rights reserved.