(2,4-dichlorobenzylideneamino)acetic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2,4-dichlorobenzylideneamino)acetic acid ethyl ester
• 英文别名: Ethyl 2-[(2,4-dichlorophenyl)methylideneamino]acetate
• 化学式: C₁₁H₁₁Cl₂NO₂
• 分子量: 260.12
• InChiKey: CFHTWUDTVBKJLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,4-dichlorobenzylideneamino)acetic acid ethyl ester 在 双氧水 、 sodium methylate 、 silver(I) acetate 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 5-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  3,5-二芳基-吡咯-2-羧酸和酯的新合成

  摘要：

  描述了吡咯-2-羧酸的新的两步合成，其步骤是通过偶氮甲亚胺的1，3偶极环加成至硝基苯乙烯，以及用碱性过氧化氢氧化所得的吡咯烷。还已经研究了在不同条件下借助于MnO 2氧化环加合物3。

  DOI：

  10.1016/s0040-4020(00)00781-x
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 、 2,4-二氯苯甲醛 在 sodium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以100%的产率得到(2,4-dichlorobenzylideneamino)acetic acid ethyl ester
  参考文献：
  名称：

  Cycloaddition reactions of glycine imine anions to phenylazocarboxylic esters – a new access to 1,3,5-trisubstituted 1,2,4-triazoles

  摘要：

  Phenylazocarboxylic tert-butyl esters have recently been shown to be highly versatile building blocks due to their ability to undergo nucleophilic aromatic substitutions under mild conditions, particularly well with [F-18]fluoride, and to act as precursors for aryl radicals. In this article, we now report first examples for cycloaddition reactions to phenylazocarboxylates. In a one-pot reaction with readily accessible glycine imines, a variety of highly substituted 1,2,4-triazoles could be obtained. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.078

文献信息

• Highly fluorescent 1,2-dihydropyrimido[1,6-α]indole: an efficient metal free synthesis and photophysical study
  作者：Tapas Das、Anirban Kayet、Ruchika Mishra、Vinod K. Singh

  DOI：10.1039/c6cc05378e

  日期：——

  A metal free route to highly fluorescent 1,2-dihydropyrimido[1,6-[small alpha]]indole derivatives has been developed via base catalyzed aldol followed by Mannich reaction of indole-2-carboxaldehyde with azomethine ylides at room temperature. This transformation...

  通过碱催化的醇醛，然后在室温下吲哚-2-羧醛与偶氮甲亚胺的曼尼希反应，已经开发出了无金属的高荧光1,2-二氢嘧啶基[1,6- [小α]]吲哚衍生物的途径。这种转变...
• Metal-Catalyzed [6 + 3] Cycloaddition of Tropone with Azomethine Ylides: A Practical Access to Piperidine-Fused Bicyclic Heterocycles
  作者：Honglei Liu、Yang Wu、Yan Zhao、Zhen Li、Lei Zhang、Wenjun Yang、Hui Jiang、Chengfeng Jing、Hao Yu、Bo Wang、Yumei Xiao、Hongchao Guo

  DOI：10.1021/ja4122268

  日期：2014.2.12

  The first metal-catalyzed [6 + 3] cycloaddition of tropone with azomethine ylides has been developed. With the use of a chiral ferrocenylphosphine-copper(I) complex as the catalyst, the asymmetric variant of the [6 + 3] cycloaddition has also been successfully achieved. The reactions proceeded smoothly under mild conditions, affording piperidine-fused bicyclic heterocycles in moderate to high yields with good to excellent diastereo- and enantioselectivies. The procedures are operationally simple and the catalysts are cheap and readily accessible, thus providing a practical approach to piperidine-fused bicyclic heterocycles.
• Tandem in situ Generation of Azomethine Ylides and Base Sensitive Nitroethylene Dipolarophiles
  作者：Imre Fejes、László Tőke、Miklós Nyerges、Chwang Siek Pak

  DOI：10.1016/s0040-4020(99)01028-5

  日期：2000.1

  We have studied the behaviour of 2-acetoxy-nitroethane derivatives in the presence of triethylamine and of an azomethine ylide generated also by the action of this base in the same reaction mixture. Under these conditions the nitro-olefins are generated and react in situ with the corresponding dipoles, giving pyrrolidine derivatives in moderate to good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A New Synthesis of Pyrrole-2-Carboxylic Acids
  作者：Chwang Siek Pak、Miklós Nyerges

  DOI：10.1055/s-1999-2797

  日期：1999.8
• Cycloaddition reactions of glycine imine anions to phenylazocarboxylic esters – a new access to 1,3,5-trisubstituted 1,2,4-triazoles
  作者：Roman Lasch、Markus R. Heinrich

  DOI：10.1016/j.tet.2015.04.078

  日期：2015.6

  Phenylazocarboxylic tert-butyl esters have recently been shown to be highly versatile building blocks due to their ability to undergo nucleophilic aromatic substitutions under mild conditions, particularly well with [F-18]fluoride, and to act as precursors for aryl radicals. In this article, we now report first examples for cycloaddition reactions to phenylazocarboxylates. In a one-pot reaction with readily accessible glycine imines, a variety of highly substituted 1,2,4-triazoles could be obtained. (C) 2015 Elsevier Ltd. All rights reserved.