3-Chlor-2-formylcrotonsaeureethylester | 85103-27-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Chlor-2-formylcrotonsaeureethylester
• 英文别名: Ethyl-3-chloro-2-formylbut-2-enoat；Ethyl 3-chloro-2-formylbut-2-enoate；ethyl 3-chloro-2-formylbut-2-enoate
• CAS: 85103-27-1
• 化学式: C₇H₉ClO₃
• 分子量: 176.6
• InChiKey: HXIZWZRSIGKIDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Chlor-2-formylcrotonsaeureethylester 在 氢氧化钾 、 乙酸酐 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 6-Brom-2-<1-ethoxycarbonyl-3-(4-nitrophenyl)-vinyliden>-2H-benzopyran
  参考文献：
  名称：

  Synthese von substituierten 2-(Ethoxycarbonyl-formyl-methylen)-2H-benzopyranen und ihre Überführung in Polymethinderivate

  摘要：

  3-Chloro-2-ethoxycarbonyl crotonic aldehyde C reacts with several 2-hydroxybenzene carbaldehydes and 2-hydroxy-naphthalene-1-carbaldehyde, respectively, to give 2-(ethoxycarbonyl-formyl-methplene)-2H-benzopyrans la-h under mild conditions. With exception of Ic and Id these compounds are mixtures of E-Z isomers. la-h easily undergo reactions, e.g. with aniline and derivatives to give 2a-e, with various CH-acidic compounds to give 3a-h and with 2-alkyl-4,6-diphenyl pyrylium salts to give 4a-e. In the presence of alcoholic hydrochloric acid, compounds 1 are converted into symmetrical 2,2'-benzopyrylotrimethine salts 5a-e which exhibit longwave absorptions from 640-705 nm. These polymethine dyes with ester groups in the methine chain exhibit a remarkable thermal stability.

  DOI：

  10.1007/bf00811675

文献信息

• Tin(IV) Chloride Complexes of β-Chlorovinyl Aldehydes: A Multinuclear Nmr Characterization in Solution
  作者：Thouraya Barhoumi-Slimi、M. A. K. Sanhoury、M. T. Ben Dhia、M. R. Khaddar

  DOI：10.1080/10426507.2012.740705

  日期：2013.9.1

  The reaction of SnCl4 with -chlorovinyl aldehydes in anhydrous dichloromethane gave a series of octahedral complexes of the general formula SnCl(4)2L (L = aldehyde). The adducts have been characterized in solution using multinuclear (H-1, C-13, and Sn-119) NMR and IR spectroscopy. Solution NMR studies show that the complexes undergo rapid ligand dissociation at ambient temperature. Ligand exchange is slowed significantly at low temperature, such that, in most of the complexes, it is possible to identify both the cis and trans isomers with predominance of the cis form. The magnitude of the metal-ligand interaction was estimated on the basis of Sn-119 NMR chemical shifts and used to classify the aldehydes studied according to their Lewis basicity.
• Synthese von substituierten 2-(Ethoxycarbonyl-formyl-methylen)-2H-benzopyranen und ihre Überführung in Polymethinderivate
  作者：Tobias Werner、Dieter Greif、Manfred Pulst、Manfred Weissenfels

  DOI：10.1007/bf00811675

  日期：1994.1

  3-Chloro-2-ethoxycarbonyl crotonic aldehyde C reacts with several 2-hydroxybenzene carbaldehydes and 2-hydroxy-naphthalene-1-carbaldehyde, respectively, to give 2-(ethoxycarbonyl-formyl-methplene)-2H-benzopyrans la-h under mild conditions. With exception of Ic and Id these compounds are mixtures of E-Z isomers. la-h easily undergo reactions, e.g. with aniline and derivatives to give 2a-e, with various CH-acidic compounds to give 3a-h and with 2-alkyl-4,6-diphenyl pyrylium salts to give 4a-e. In the presence of alcoholic hydrochloric acid, compounds 1 are converted into symmetrical 2,2'-benzopyrylotrimethine salts 5a-e which exhibit longwave absorptions from 640-705 nm. These polymethine dyes with ester groups in the methine chain exhibit a remarkable thermal stability.