4-ethyl-5-formyl-3-methyl-pyrrole-2-carboxylic acid | 4949-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-ethyl-5-formyl-3-methyl-pyrrole-2-carboxylic acid
• 英文别名: 4-Ethyl-5-formyl-3-methyl-pyrrolcarbonsaeure-(2)；2-Formyl-3-ethyl-4-methylpyrrole-5-carboxylic acid；4-ethyl-5-formyl-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 4949-42-2
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: BKRXHZDKBFPBSE-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  375.2±42.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-5-formyl-3-methyl-pyrrole-2-carboxylic acid 在 水 、 氢溴酸 、 溴 、 sodium methylate 、 溶剂黄146 作用下， 生成 5'-Oxo-4-<β-carboxy-ethyl>-3,4'-dimethyl-3'-ethyl-1',5'-dihydro-dipyrromethen-(2,2'), Neoxanthobilirubinsaeure
  参考文献：
  名称：

  Siedel; Fischer, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1933, vol. 214, p. 145,152, 167

  摘要：

  DOI：
• 作为产物：
  描述：

  5-dichloromethyl-4-ethyl-3-methyl-pyrrole-2-carboxylic acid benzyl ester 在 氢气 作用下， 生成 4-ethyl-5-formyl-3-methyl-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  一种方便的合成途径来合成细菌绿素

  摘要：

  A，C-二乙烯基卟啉与活化的亲二烯体的反应产生稳定的bis Diels-Alder加合物，其吸收波长大于735 nm的光。这提供了方便的一般途径来产生类似细菌绿素的生色团。

  DOI：

  10.1016/0040-4039(91)80636-k

文献信息

• Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines
  作者：Papireddy Kancharla、Kevin A. Reynolds

  DOI：10.1016/j.tet.2013.07.067

  日期：2013.9

  Facile, versatile, and cost-effective synthetic routes for the preparation of a range of new 3-alkyl-, 4-alkyl-, 3,4-dialkyl-, and 3-halo-4-alkyl-2,2′-bipyrrole-5-carboxaldehydes have been developed. These 2,2′-bipyrrole-5-carboxaldehydes offer interesting potential as building blocks for making bioactive natural and unnatural products, as demonstrated by the synthesis of B-ring functionalized prodiginines

  已经开发出用于制备一系列新型 3-烷基-、4-烷基-、3,4-二烷基-和 3-卤代-4-烷基-2,2′-联吡咯-5-甲醛的简单、多功能和具有成本效益的合成路线。这些 2,2′-联吡咯-5-甲醛作为制造生物活性天然和非天然产物的构建块具有有趣的潜力，正如 B 环官能化 prodiginines （PG） 和 tambjamines 的合成所证明的那样。
• One-pot synthesis of corrolates by cobalt catalyzed cyclization of formylpyrroles
  作者：Roberto Paolesse、Emanuela Tassoni、Silvia Licoccia、Maurizio Paci、Tristano Boschi

  DOI：10.1016/0020-1693(95)04747-6

  日期：1996.1

  2-Formylpyrroles react in the presence of cobalt ions to afford a mixture of porphyrin and corrole cobalt complexes. This is the first example of a single step synthesis of meso-unsubstituted corrole from a monopyrrole. When 3-ethyl-4-methyl-2-formylpyrrole-5-carboxylic acid was used as starting material, Co(Etioporphyrin-I) and a mixture of cobalt corrolates were obtained. Chromatographic separation

  2-甲酰基吡咯在钴离子的存在下反应，得到卟啉和Corrole钴配合物的混合物。这是从单吡咯单步合成内消旋取代的甲氧基的第一个例子。当使用3-乙基-4-甲基-2-甲酰基吡咯-5-羧酸作为起始原料时，得到Co（Etioporphyrin-I）和钴酸钴的混合物。对这些化合物进行色谱分离和1 H NMR的详细分析，可将其鉴定为两种不同的乙二胺样酚。报告了可能的反应途径，解释了它们的形成。与钴不同的金属仅给出相应的卟啉配合物（Ni，Cu）。在Mn或Rh的存在下根本没有观察到环化。
• Electrode catalysis of the four-electron reduction of oxygen to water by dicobalt face-to-face porphyrins
  作者：James P. Collman、Peter Denisevich、Yutaka Konai、Matt Marrocco、Carl Koval、Fred C. Anson

  DOI：10.1021/ja00539a009

  日期：1980.9

  A series of dimeric metalloporphyrin molecules has been synthesized in which the two porphyrin rings are constrained to lie parallel to one another by two amide bridges of varying length that link the rings together. These cofacial metalloporphyrins have been applied to the surface of graphite electrodes and tested for catalytic activity toward the electroreduction of dioxygen to water in aqueous acidic

  已经合成了一系列二聚金属卟啉分子，其中两个卟啉环被两个不同长度的酰胺桥限制为彼此平行，将环连接在一起。这些共面金属卟啉已被应用于石墨电极的表面，并测试了在酸性水溶液中将分子氧电还原为水的催化活性。所有测试的分子都表现出一定的催化活性，但过氧化氢而不是水是主要的还原产物。然而，由四原子桥连接的二钴共面卟啉几乎完全催化还原为水，并且具有非常正的电位。采用旋转环盘伏安测量来诊断电极反应途径，并提出了观察到的催化作用的可能机制。结果似乎证明了两个金属中心参与控制多电子过程的过程。
• Indolinone combinatorial libraries and related products and methods for the treatment of disease
  申请人：Tang Cho Peng

  公开号：US20050197382A1

  公开（公告）日：2005-09-08

  The present invention relates to organic molecules capable of modulating, regulating and/or inhibiting protein kinase signal transduction. Such compounds are useful for the treatment of diseases related to unregulated protein kinase signal transduction, including cell proliferative diseases such as cancer, atherosclerosis, arthritis and restenosis and metabolic diseases such as diabetes. The present invention features indolinone compounds that potently inhibit protein kinases and related products and methods. Inhibitors specific to the FLK protein kinase can be obtained by adding chemical substituents to the 3-[(indole-3-yl)methylene]-2-indolinone, in particular at the 1′ position of the indole ring. Indolinone compounds that specifically inhibit the FLK and platelet derived growth factor protein kinases can harbor a tetrahydroindole or cyclopentano-b-pyrrol moiety. Indolinone compounds that are modified with substituents, particularly at the 5 position of the oxindole ring, can effectively activate protein kinases. This invention also features novel hydrosoluble indolinone compounds that are tyrosine kinase inhibitors and related products and methods.

  本发明涉及有机分子，能够调节、调控和/或抑制蛋白激酶信号转导。这些化合物对于治疗与不受调节的蛋白激酶信号转导相关的疾病非常有用，包括细胞增殖性疾病，如癌症、动脉粥样硬化、关节炎、再狭窄和代谢性疾病，如糖尿病。本发明涉及具有强效抑制蛋白激酶和相关产品以及方法的吲哚酮化合物。特定于FLK蛋白激酶的抑制剂可以通过在吲哚环的1'位置添加化学取代基来获得3-[(吲哚-3-基)亚甲基]-2-吲哚酮。特异性抑制FLK和血小板衍生生长因子蛋白激酶的吲哚酮化合物可以具有四氢吲哚或环戊烯基-β-吡咯基。在氧吲哚环的5位取代基的修饰下，吲哚酮化合物可以有效激活蛋白激酶。本发明还涉及新型水溶性吲哚酮化合物，它们是酪氨酸激酶抑制剂和相关产品和方法。
• Fischer et al., Justus Liebigs Annalen der Chemie, 1930, vol. 480, p. 109,122, 155
  作者：Fischer et al.

  DOI：——

  日期：——