(Z)-3-chloro-3-(2-methoxyphenyl)acrylaldehyde | 165334-43-0

• 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)-3-chloro-3-(2-methoxyphenyl)acrylaldehyde
• 英文别名: (Z)-3-chloro-3-(2-methoxyphenyl)prop-2-enal
• CAS: 165334-43-0
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: RLXBOOHXRSMLGH-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid O-ethyl ester S-[2-oxo-2-(3,4,5-trimethoxyphenyl)-ethyl] ester 、 (Z)-3-chloro-3-(2-methoxyphenyl)acrylaldehyde 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以69%的产率得到[5-(2-Methoxyphenyl)thiophen-2-yl]-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of thiophene analogues of chalcones

  摘要：

  Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative activity and inhibition of tubulin assembly and colchicine binding to tubulin. The replacement of the double bond with a thiophene maintains antiproliferative activity and therefore must not significantly alter the relative conformation of the two aryl rings. The synthesized compounds were found to inhibit the growth of several cancer cell lines at nanomolar to low micromolar concentrations. In general, all compounds having significant antiproliferative activity inhibited tubulin polymerization with an IC50 < 2 mu M. Several of these compounds caused K562 cells to arrest in the G2/M phase of the cell cycle. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.026
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 9.5h， 生成 (Z)-3-chloro-3-(2-methoxyphenyl)acrylaldehyde
  参考文献：
  名称：

  取代基的3-芳基（杂芳基）-3-氯丙烯醛和四氢异喹啉的碱促进的分子间环化：一种获得吡咯并[2,1- a ]异喹啉的方法

  摘要：

  我们已经开发了一种新的碱促进的在一锅中取代的3-芳基（杂芳基）-3-氯丙烯醛和四氢异喹啉的分子间级联环化反应。该反应提供了吡咯并[2，1- a ]异喹啉的简便实用的合成方法。合成了许多吡咯并[2,1- a ]异喹啉，中度至高产率（高达97％）。

  DOI：

  10.1021/acs.joc.6b01781

文献信息

• On the Regio and Stereo Selective Formylations of Acyclic Alpha Methylene Ketones towards Vilsmeier Haack Reagent
  作者：Arindam Chakraborty、Jayanta K. Ray

  DOI：10.1080/00397919508015433

  日期：1995.6

  The regio and stereo selectivities of Vilsmeier Haack reaction of ketomethylene compounds have been predicted. The possible mechanistic pathway has also been proposed.
• Base-Promoted Intermolecular Cyclization of Substituted 3-Aryl(Heteroaryl)-3-chloroacrylaldehydes and Tetrahydroisoquinolines: An Approach to Access Pyrrolo[2,1-<i>a</i>]isoquinolines
  作者：Ziqi Yang、Ning Lu、Zhonglin Wei、Jungang Cao、Dapeng Liang、Haifeng Duan、Yingjie Lin

  DOI：10.1021/acs.joc.6b01781

  日期：2016.12.2

  We have developed a new base-promoted intermolecular cascade cyclization reaction of substituted 3-aryl(heteroaryl)-3-chloroacrylaldehydes and tetrahydroisoquinolines in one pot. The reaction provides a facile and practical synthesis of pyrrolo[2,1-a]isoquinolines. A number of pyrrolo[2,1-a]isoquinolines were synthesized in moderate to high yields (up to 97%).

  我们已经开发了一种新的碱促进的在一锅中取代的3-芳基（杂芳基）-3-氯丙烯醛和四氢异喹啉的分子间级联环化反应。该反应提供了吡咯并[2，1- a ]异喹啉的简便实用的合成方法。合成了许多吡咯并[2,1- a ]异喹啉，中度至高产率（高达97％）。
• Design, synthesis, and biological evaluation of thiophene analogues of chalcones
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Olga Cruz-Lopez、Delia Preti、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Nicola Zonta、Jan Balzarini、Andrea Brancale、Taradas Sarkar、Ernest Hamel

  DOI：10.1016/j.bmc.2008.04.026

  日期：2008.5

  Chalcones are characterized by possessing an enone moiety between two aromatic rings. A series of chalcone-like agents, in which the double bond of the enone system is embedded within a thiophene ring, were synthesized and evaluated for antiproliferative activity and inhibition of tubulin assembly and colchicine binding to tubulin. The replacement of the double bond with a thiophene maintains antiproliferative activity and therefore must not significantly alter the relative conformation of the two aryl rings. The synthesized compounds were found to inhibit the growth of several cancer cell lines at nanomolar to low micromolar concentrations. In general, all compounds having significant antiproliferative activity inhibited tubulin polymerization with an IC50 < 2 mu M. Several of these compounds caused K562 cells to arrest in the G2/M phase of the cell cycle. (C) 2008 Elsevier Ltd. All rights reserved.