2,4-二乙基-3-乙基-1H-吡咯-2,4-二羧酸酯 | 52921-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2,4-二乙基-3-乙基-1H-吡咯-2,4-二羧酸酯
• 英文名称: 3-ethyl-1H-pyrrole-2,4-dicarboxylic acid diethyl ester
• 英文别名: 3-ethyl-pyrrole-2,4-dicarboxylic acid diethyl ester；3-Aethyl-pyrrol-2,4-dicarbonsaeure-diaethylester；3-Ethylpyrrole-2,4-dicarboxylic Acid Diethyl Ester；3-Ethyl-2,4-bis-ethoxycarbonyl-pyrrol；Diethyl 3-ethyl-1H-pyrrole-2,4-dicarboxylate
• CAS: 52921-22-9
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: KCKGICNBLYZXQD-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  397.6±42.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二乙基-3-乙基-1H-吡咯-2,4-二羧酸酯 在 氯化亚砜 、 二苯基膦酰羟胺 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 [4-(1-Benzyl-1H-indazol-5-ylamino)-5-ethyl-pyrrolo[2,1-f][1,2,4]triazin-6-yl]-acetonitrile
  参考文献：
  名称：

  New dual inhibitors of EGFR and HER2 protein tyrosine kinases

  摘要：

  A novel series of dual EGFR and HER2 inhibitors based on the pyrrolo[2,1-f][1,2,4]triazine nucleus is described. A general route toward their synthesis, which enables functionalization at multiple sites, has been developed. Biological evaluation in enzymatic and cell-based assays has identified a series of C-6 carbamates with potent biochemical and cellular activities.

  DOI：

  10.1016/j.bmcl.2005.07.027
• 作为产物：
  描述：

  4-ethyl-pyrrole-2,3,5-tricarboxylic acid-3,5-diethyl ester 在 sodium hydroxide 、 溴 、 镍 、 溶剂黄146 作用下， 生成 2,4-二乙基-3-乙基-1H-吡咯-2,4-二羧酸酯
  参考文献：
  名称：

  Nicolaus; Nicoletti, Annali di Chimica, 1957, vol. 47, p. 167,172

  摘要：

  DOI：

文献信息

• Pyrrolotriazine inhibitors of kinases
  申请人：Bristol Myers Squibb Company

  公开号：US06982265B1

  公开（公告）日：2006-01-03

  The present invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit the tyrosine kinase activity of growth factor receptors such as VEGFR-2, FGFR-1, PDGFR, HER-1, HER-2, thereby making them useful as anti-cancer agents. The formula I compounds are also useful for the treatment of other diseases associated with signal transduction pathways operating through growth factor receptors.

  本发明提供了公式I的化合物及其药用可接受的盐。公式I的化合物抑制了诸如VEGFR-2、FGFR-1、PDGFR、HER-1、HER-2等生长因子受体的酪氨酸激酶活性，从而使其作为抗肿瘤剂具有用途。公式I的化合物也用于治疗通过生长因子受体运作的信号转导通路相关的其他疾病。
• Nonionic Superbase-Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and .alpha.-C-Acyl Amino Acid Esters
  作者：Jiansheng Tang、John G. Verkade

  DOI：10.1021/jo00104a041

  日期：1994.12

  The reaction of acyl chlorides or acid anhydrides with isocyanoacetates in the presence of the superior strong nonionic base P(MeNCH(2)CH(2))(3)N (1) gave oxazoles in 98-99% yield. Treatment of the oxazoles with HCl-MeOH gave alpha-C-acyl amino acid esters in 81-82% yield. The reaction of beta-acetoxy-alpha-nitroalkanes or nitroalkenes with isocyanoacetates in the presence of 1 gave pyrroles in 100% yield. The conjugate acid of 1 can be treated with KO-t-Bu to regenerate 1. Treatment of the pyrroles with LiAlH4, followed by PTSA-CH2(OMe)(2) and oxidation gave porphyrins in 65-69% yield. LiCl, which functions both as a strong nucleophile in the S(N)2 demethylation of the 5,5'-bis(methoxycarbonyl)-3,3',4,4'-tetramethyldipyrromethane 22a and as a Lewis acid in the electrophilic substitution cyclization of paraformaldehyde at dipyrromethane, facilitates the combination of four reactions into a one-pot synthesis of octaethylporphyrin in 67% yield from 22a.
• Remarkable solvent effect in Barton–Zard pyrrole synthesis: application in an efficient one-step synthesis of pyrrole derivatives
  作者：Apurba Bhattacharya、Sankara Cherukuri、Robert Erik Plata、Nitinchandra Patel、Victoriano Tamez、John A. Grosso、Michael Peddicord、Venkatapuram A. Palaniswamy

  DOI：10.1016/j.tetlet.2006.05.167

  日期：2006.7

  A unique solvent effect encountered in the Barton-Zard pyrrole synthesis was exploited to develop an efficient synthesis of pyrrole-2-esters. The chemistry was extended to a one-pot synthesis of pyrrole-2,4-dicarboxylates. (c) 2006 Elsevier Ltd. All rights reserved.
• An efficient electrophilic N-amination utilizing in situ generated chloramine under phase transfer conditions
  作者：Apurba Bhattacharya、Nitin C. Patel、Robert Erik Plata、Michael Peddicord、Qingmei Ye、Luca Parlanti、Venkatapuram A. Palaniswamy、John A. Grosso

  DOI：10.1016/j.tetlet.2006.05.102

  日期：2006.7

  An efficient, one-pot, phase transfer N-amination technology was developed. The protocol utilizes chloramine, an inexpensive and safe electrophilic aminating agent potentially viable for commercial manufacturing. (c) 2006 Elsevier Ltd. All rights reserved.
• PYRROLOTRIAZINE INHIBITORS OF KINASES
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1183033A1

  公开（公告）日：2002-03-06