3-chloro-3-(o-tolyl)acrylaldehyde | 90797-90-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3-chloro-3-(o-tolyl)acrylaldehyde
• 英文别名: β-Chlor-o-methylzimtaldehyd；3-Chloro-3-(2-methylphenyl)prop-2-enal；3-chloro-3-(2-methylphenyl)prop-2-enal
• CAS: 90797-90-3
• 化学式: C₁₀H₉ClO
• 分子量: 180.634
• InChiKey: GDJMLQFWMAVPDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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

• 作为反应物：
  描述：

  3-chloro-3-(o-tolyl)acrylaldehyde 、 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67%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

• Synthesis of 2-Mercaptobenzaldehyde, 2-Mercaptocyclohex-1-enecarboxaldehydes and 3-Mercaptoacrylaldehydes
  作者：Qingfen Niu、Xiaofeng Xu、Hongjian Sun、Xiaoyan Li

  DOI：10.1002/cjoc.201200433

  日期：2012.10

  for the preparation of 2‐mercaptobenzaldehyde, 2‐mercaptocyclohex‐1‐enecarboxaldehydes and 3‐mercaptoacrylaldehydes [(Z)‐3‐mercapto‐2‐methyl‐3‐phenylacrylaldehyde, 3‐mercapto‐3‐(o‐tolyl)acrylaldehyde)] starting from ortho‐bromobenzaldehyde, 2‐chlorocyclohex‐1‐enecarbaldehydes, (Z)‐3‐chloro‐2‐methyl‐3‐phenylacrylaldehyde and 3‐chloro‐3‐(o‐tolyl)acrylaldehyde is reported. The reaction of sulfur with the

  一种新颖的一锅法制备2-巯基苯甲醛，2-巯基环己-1-烯醛和3-巯基丙烯醛[（Z）-3-巯基-2-甲基-3-苯基丙烯醛，3-巯基3-（o -[甲苯基）丙烯醛]]从邻-溴苯甲醛，2-氯环己基-1-烯醛，（Z）-3-氯-2-甲基-3-苯基丙烯醛和3-氯-3-（邻甲苯基）丙烯醛开始。硫与乙缩醛的格氏试剂用于保护醛基的反应通过用稀盐酸水解以高产率提供标题化合物。
• 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.