triethyl 2,3,4-quinolinetricarboxylate | 1221405-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: triethyl 2,3,4-quinolinetricarboxylate
• 英文别名: Triethyl quinoline-2,3,4-tricarboxylate；triethyl quinoline-2,3,4-tricarboxylate
• CAS: 1221405-91-9
• 化学式: C₁₈H₁₉NO₆
• 分子量: 345.352
• InChiKey: LFNGSMHQNUHGNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  靛红 、 丁炔二酸二乙酯 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以72%的产率得到triethyl 2,3,4-quinolinetricarboxylate
  参考文献：
  名称：

  A Novel One-Pot Synthesis of Substituted Quinolines

  摘要：

  AbstractA synthesis of quinoline derivatives is described via reaction between ethyl bromopyruvate (=ethyl 3‐bromo‐2‐oxopropanoate), acetylenedicarboxylate, and isatin (=1H‐indole‐2,3‐dione) in the presence of NaH as a base. Also, these reactions were performed without ethyl bromopyruvate. The reaction in the presence of ethyl bromopyruvate provides regioselectively a quinoline with the ethyl ester group in 4‐position. In the absence of ethyl bromopyruvate, the reaction leads to functionalized quinolines with the same ester groups in 2‐, 3‐, and 4‐positions.

  DOI：

  10.1002/hlca.200900304

文献信息

• A Facile One-Pot Synthesis of Substituted Quinolines via New Multicomponent Reaction
  作者：Amir Rineh、Mohammad A. Khalilzadeh、Mohammad M. Hashemi、Medí Rajabi、Fatemeh Karimi

  DOI：10.1002/jhet.858

  日期：2012.7

  An efficient synthesis of quinoline derivatives is described via the reaction between ethyl chloropyruvate or alkyl 4‐chloroacetoacetate and activated acetylenic compounds in the presence of nucleophilic form of isatin in water as the solvent. Nucleophilic form of isatin is produced from the reaction of isatin and triethylamin.

  喹啉衍生物的有效合成描述通过在靛红的亲核形式的在水的存在下作为溶剂乙基chloropyruvate或烷基4-氯乙酰和活化的乙炔基化合物之间的反应。Isatin的亲核形式是由isatin和三乙胺的反应产生的。
• Formation of trialkyl quinoline-2,3,4-tricarboxylates by reaction of isatin, dialkyl acetylenedicarboxylates, and sodium O-alkyl carbonodithioates
  作者：Issa Yavari、Samereh Seyfi、Zinatossadat Hossaini

  DOI：10.1016/j.tetlet.2010.02.107

  日期：2010.4

  An efficient one-pot synthesis of quinoline-2,3,4-tricarboxylates is described by reaction of isatin (indoline-2,3-dione) and electron-deficient acetylenic esters in the presence of sodium O-alkyl carbonodithioates, themselves prepared by addition of sodium hydride to a solution of an alcohol in CS2. (C) 2010 Published by Elsevier Ltd.
• Nano KF/Clinoptilolite: An Effective Heterogeneous Base Nanocatalyst for Synthesis of Substituted Quinolines in Water
  作者：Hadi Sajjadi-Ghotbabadi、Shahrzad Javanshir、Faramarz Rostami-Charati

  DOI：10.1007/s10562-015-1652-y

  日期：2016.2

  A proficient, green and environmentally benign one-pot three-component synthesis of functionalized quinolines was developed by condensation reactions of isatin, activated acetylenic compounds, and alcohols in the presence of KF/CP (NPs) as a heterogeneous base nanocatalyst, at room temperature in water.[GRAPHICS]
• A Novel One-Pot Synthesis of Substituted Quinolines
  作者：Maryam Sabbaghan、Issa Yavari、Zinatossadat Hossaini、Sanaz Souri

  DOI：10.1002/hlca.200900304

  日期：2010.5

  AbstractA synthesis of quinoline derivatives is described via reaction between ethyl bromopyruvate (=ethyl 3‐bromo‐2‐oxopropanoate), acetylenedicarboxylate, and isatin (=1H‐indole‐2,3‐dione) in the presence of NaH as a base. Also, these reactions were performed without ethyl bromopyruvate. The reaction in the presence of ethyl bromopyruvate provides regioselectively a quinoline with the ethyl ester group in 4‐position. In the absence of ethyl bromopyruvate, the reaction leads to functionalized quinolines with the same ester groups in 2‐, 3‐, and 4‐positions.