(Z)-3-氯-3-(噻吩-3-基)丙烯醛 | 1036271-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: (Z)-3-氯-3-(噻吩-3-基)丙烯醛
• 英文名称: (Z)-3-chloro-3-(thiophen-3-yl)acrylaldehyde
• 英文别名: (2Z)-3-chloro-3-(thiophen-3-yl)prop-2-enal；(Z)-3-chloro-3-thiophen-3-ylprop-2-enal
• CAS: 1036271-74-5
• 化学式: C₇H₅ClOS
• mdl: MFCD13176396
• 分子量: 172.635
• InChiKey: AUILAZLQUNYBRO-XFSBKJJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 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-氯-3-(噻吩-3-基)丙烯醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以54%的产率得到(5-Thiophen-3-ylthiophen-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：

  3-乙酰基噻吩 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 6.17h， 生成 (Z)-3-氯-3-(噻吩-3-基)丙烯醛
  参考文献：
  名称：

  Ugi 反应，然后是分子内 Diels-Alder 反应和 HCl 的消除：芳烃融合异吲哚酮的一锅法

  摘要：

  已经开发了一种涉及四组分 Ugi 反应，然后是分子内 Diels-Alder 反应/HCl 消除级联反应的一锅法，以提供以多样性为导向的异吲哚酮框架的快速访问。已经针对所有四个组件研究了该过程的范围，并给出了一锅法和顺序方法之间的比较。已经探索了通过 Suzuki 耦合进行后期一锅功能化的可能性。

  DOI：

  10.1002/ejoc.201700747

文献信息

• Ugi Reaction Followed by Intramolecular Diels-Alder Reaction and Elimination of HCl: One-Pot Approach to Arene-Fused Isoindolinones
  作者：Jianjun Huang、Xiaochen Du、Kristof Van Hecke、Erik V. Van der Eycken、Olga P. Pereshivko、Vsevolod A. Peshkov

  DOI：10.1002/ejoc.201700747

  日期：2017.8.17

  A one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels–Alder reaction/HCl elimination cascade has been developed to provide rapid access to the isoindolinone framework in a diversity-oriented fashion. The scope of the process has been investigated with respect to all four components, and a comparison between the one-pot and sequential approaches is given. The

  已经开发了一种涉及四组分 Ugi 反应，然后是分子内 Diels-Alder 反应/HCl 消除级联反应的一锅法，以提供以多样性为导向的异吲哚酮框架的快速访问。已经针对所有四个组件研究了该过程的范围，并给出了一锅法和顺序方法之间的比较。已经探索了通过 Suzuki 耦合进行后期一锅功能化的可能性。
• Efficient Synthesis of 4- and 5-Substituted 2-Aminopyrimidines by Coupling of β-Chlorovinyl Aldehydes and Guanidines
  作者：Anna S. Komendantova、Alexander V. Komkov、Yulia A. Volkova、Igor V. Zavarzin

  DOI：10.1002/ejoc.201700737

  日期：2017.8.10

  A general, practical and simple synthesis of functionalized 2-aminopyrimidines starting from β-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently incorporated into the pyrimidine derivatives by two-step sequence involving the Vilsmeier-Haack reaction followed by the condensation with guanidines. The protocol is distinguished

  据报道，从β-氯乙烯基醛和am开始的官能化的2-氨基嘧啶的一般，实用和简单的合成。在碳酸钾的存在下，通过涉及维斯迈尔-哈克（Vilsmeier-Haack）反应，然后与胍缩合的两步顺序，各种酮已被有效地掺入嘧啶衍生物中。该协议的特点是操作简便，试剂价格低廉和官能团耐受性强。在许多情况下，无需使用柱色谱法即可以高至极好的收率获得纯净的固体产品。该方法的合成价值通过甾族嘧啶和抗肿瘤药Imatinib和Mocetinostat的前体的有效合成得到证明。
• 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.