3-氯-3-(4-乙基苯基)丙-2-烯醛 | 61519-33-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 3-氯-3-(4-乙基苯基)丙-2-烯醛
• 英文名称: (E)-3-Chloro-3-(4-ethyl-phenyl)-propenal
• 英文别名: 3-Chloro-3-(4-ethylphenyl)prop-2-enal；3-chloro-3-(4-ethylphenyl)prop-2-enal
• CAS: 61519-33-3
• 化学式: C₁₁H₁₁ClO
• 分子量: 194.661
• InChiKey: MJHJKAPOAQYJRN-UHFFFAOYSA-N

物化性质

• 沸点：
  300.5±21.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  3-氯-3-(4-乙基苯基)丙-2-烯醛 、 1,3-丙二醇 在 对甲苯磺酸 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 以59%的产率得到
  参考文献：
  名称：

  Metal-free, PTSA catalyzed facile synthesis of β-ketoacetal from β-chlorocinnamaldehyde

  摘要：

  A toluene solution of beta-chlorocinnamaldehyde and dihydroxy alcohols in the catalytic presence of paratoluenesulphonic acid (PTSA) yield the beta-ketoacetal in good to outstanding amount. The catalyst (PTSA), first selectively protect the aldehydic group to form the beta-chloroacetal and the subsequent dechlorination by H2O result the beta-ketoacetal. Significant transformation was achieved with electron donating substituent attached at the para-position of cinnamaldehyde. The selective formation of beta-keto-1,3-acetal was also obtained with a mixture of 1, 2- and 1, 3- diol. The present reaction consists of a metal-free, economical, robustly feasible, sizeable functional group tolerance and high yield properties. Moreover, the use of different dihydroxy alcohols made this process more benign and valuable towards the metal-free development of ketones. First, of its kind, a rare and unusual multitasking nature of PTSA is observed. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.07.022

文献信息

• Metal-free, PTSA catalyzed facile synthesis of β-ketoacetal from β-chlorocinnamaldehyde
  作者：Avinash K. Srivastava、Munsaf Ali、Kamal Nayan Sharma、Raj K. Joshi

  DOI：10.1016/j.tetlet.2018.07.022

  日期：2018.8

  A toluene solution of beta-chlorocinnamaldehyde and dihydroxy alcohols in the catalytic presence of paratoluenesulphonic acid (PTSA) yield the beta-ketoacetal in good to outstanding amount. The catalyst (PTSA), first selectively protect the aldehydic group to form the beta-chloroacetal and the subsequent dechlorination by H2O result the beta-ketoacetal. Significant transformation was achieved with electron donating substituent attached at the para-position of cinnamaldehyde. The selective formation of beta-keto-1,3-acetal was also obtained with a mixture of 1, 2- and 1, 3- diol. The present reaction consists of a metal-free, economical, robustly feasible, sizeable functional group tolerance and high yield properties. Moreover, the use of different dihydroxy alcohols made this process more benign and valuable towards the metal-free development of ketones. First, of its kind, a rare and unusual multitasking nature of PTSA is observed. (C) 2018 Elsevier Ltd. All rights reserved.