(Z)-2-(chloromethyl)-3-phenylacrylaldehyde | 54827-32-6

• 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-(chloromethyl)-3-phenylacrylaldehyde
• 英文别名: (Z)-α-chloromethylcinnamaldehyde；(Z)-2-(chloromethyl)-3-phenylprop-2-enal
• CAS: 54827-32-6
• 化学式: C₁₀H₉ClO
• 分子量: 180.634
• InChiKey: LQJJTRMLZKTIKD-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  (Z)-2-(chloromethyl)-3-phenylacrylaldehyde 在 葡萄糖 、 水 作用下， 反应 48.0h， 以33%的产率得到(2R)-2-methyl-3-phenyl-1-propanol
  参考文献：
  名称：

  On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

  摘要：

  The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes. as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.02.003
• 作为产物：
  描述：

  methyl (2Z)-2-(chloromethyl)-3-phenylprop-2-enoate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (Z)-2-(chloromethyl)-3-phenylacrylaldehyde
  参考文献：
  名称：

  On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

  摘要：

  The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes. as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.02.003

文献信息

• Depezay, Jean-Claude; Merrer Le, Yves, Bulletin de la Societe Chimique de France, 1981, vol. 2, # 7-8, p. 306 - 312
  作者：Depezay, Jean-Claude、Merrer Le, Yves

  DOI：——

  日期：——
• Depazay,J.-C.; Le Merrer,Y., Tetrahedron Letters, 1974, p. 2751 - 2754
  作者：Depazay,J.-C.、Le Merrer,Y.

  DOI：——

  日期：——