(Z)-2-chloro-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-enal | 1044761-63-8

• 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-(3-methoxy-4-phenylmethoxyphenyl)prop-2-enal
• CAS: 1044761-63-8
• 化学式: C₁₇H₁₅ClO₃
• 分子量: 302.757
• InChiKey: GOHDEUJAUPQJTG-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2,2-三氯-1-乙氧基乙醇 、 4-苄氧基-3-甲氧基苯甲醛 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以85%的产率得到(Z)-2-chloro-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-enal
  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

• 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.