2-(Ethoxycarbonyl-formyl-methylen)-2H-benzopyran | 136440-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(Ethoxycarbonyl-formyl-methylen)-2H-benzopyran
• 英文别名: ethyl 2-chromen-2-ylidene-3-oxopropanoate
• CAS: 136440-10-3
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: KNAXSJOKKOBFGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Ethoxycarbonyl-formyl-methylen)-2H-benzopyran 在 盐酸 、 高氯酸 作用下， 以 乙醇 为溶剂， 以70%的产率得到
  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
• 作为产物：
  描述：

  3-Chlor-2-formylcrotonsaeureethylester 、 水杨醛 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以50%的产率得到2-(Ethoxycarbonyl-formyl-methylen)-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