ethyl 5-acetyl-pyrrole-2-carboxylate | 119647-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-acetyl-pyrrole-2-carboxylate
• 英文别名: Ethyl 5-acetyl-1H-pyrrole-2-carboxylate
• CAS: 119647-70-0
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: UMAGGVUZZDOQKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-acetyl-pyrrole-2-carboxylate 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到5-乙酰基-1H-吡咯-2-羧酸
  参考文献：
  名称：

  Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action

  摘要：

  13C NMR 和质谱研究已用于证明 N-磺酰羟甲基吡咯抑制剂 (10) 对 α-胰凝乳蛋白酶的抑制是非共价的。已合成了在替代的 C2 位置引入吸电子基团（酰基取代基）的羟基烷基吡咯，并且还显示出可使 α-胰凝乳蛋白酶失活。对此类的 SAR 研究表明，在 C2 处掺入苯丙氨酸是有利的，但在 C5 处引入疏水取代基几乎没有什么好处。

  DOI：

  10.1039/b302411c
• 作为产物：
  描述：

  (R,S)-ethyl 5-(1-hydroxyethyl)-1H-pyrrole-2-carboxylate 在 戴斯-马丁氧化剂 作用下， 以96%的产率得到ethyl 5-acetyl-pyrrole-2-carboxylate
  参考文献：
  名称：

  2-Aminobenzimidazoles as potent ITK antagonists: de novo design of a pyrrole system targeting additional hydrogen bonding interaction

  摘要：

  Based on information from molecular modeling, a series of 2-aminobenzimidazoles with pyrrole moieties were designed and synthesized as ITK antagonists. Results showed that a significant improvement of intrinsic and cell-based potency was achieved. X-ray crystallographic analysis of an inhibitor complex with ITK confirmed the prediction from the de novo design that the pyrrole moiety of the inhibitor would form an additional hydrogen bonding interaction with Glu436 in the catalytic domain, and hence improve overall binding affinity of the inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.057

文献信息

• Electron-withdrawing group effect in aryl group of allyl bromides for the successful synthesis of indolizines via a novel [3+3] annulation approach
  作者：Sujin Park、Ikyon Kim

  DOI：10.1016/j.tet.2015.02.013

  日期：2015.4

  A new synthetic approach to 6,7-disubstituted indolizines has been developed from pyrrole-2-carboxaldehydes and allyl bromides via two successive base-mediated reactions. As three-carbon units for formation of pyridine moiety of indolizines, allyl bromides easily derived from Morita–Baylis–Hillman (MBH) adducts were employed. We found that positioning electron-withdrawing group(s) at the aromatic ring

  通过两个连续的碱介导的反应，由吡咯-2-羧醛和烯丙基溴开发了一种新的合成方法来合成6,7-二取代的吲哚嗪。作为形成吲哚嗪吡啶部分的三碳单元，采用了容易从森田-贝利斯-希尔曼（MBH）加合物衍生的烯丙基溴。我们发现，在烯丙基溴的芳香环上放置吸电子基团是成功闭环的关键，以允许获得具有独特取代方式的吲哚嗪。同样通过该方法组装结构上相关的咪唑并[1,2- a ]吡啶和吡啶并[1,2- a ]吲哚。
• Synthetic Studies on Indoles and Related Compounds. XXXVIII. .BETA.-Acylation of Ethyl Pyrrole-2-carboxylate by Friedel-Crafts Acylation: Scope and Limitations.
  作者：Masanobu TANI、Takahiro ARIYASU、Chika NISHIYAMA、Hiroko HAGIWARA、Toshiko WATANABE、Yuusaku YOKOYAMA、Yasuoki MURAKAMI

  DOI：10.1248/cpb.44.48

  日期：——

  The Friedel-Crafts acylation of ethyl pyrrole-2-carboxylate (3) was studied under several conditions using various Lewis acids and acyl chlorides. The acylation with various acyl chlorides in the presence of aluminum chloride gave exclusively ethyl 4-acylpyrrole-2-carboxylate (5), whereas weaker Lewis acids such as zinc chloride and boron trifluoride etherate gave a mixture of ethyl 4- and 5-acylpyrrole-2-carboxylates.

  在多种条件下，使用各种路易斯酸和酰基氯对吡咯-2-羧酸乙酯（3）的弗里德尔-卡夫酰化进行了研究。在有氯化铝存在的情况下，用各种酰基氯进行酰化反应，只得到 4-酰基吡咯-2-羧酸乙酯（5），而用氯化锌和三氟化硼醚酸等较弱的路易斯酸进行酰化反应，则得到 4-酰基吡咯-2-羧酸乙酯和 5-酰基吡咯-2-羧酸乙酯的混合物。
• Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action
  作者：Derek C. Martyn、Andrea J. Vernall、Bruce M. Clark、Andrew D. Abell

  DOI：10.1039/b302411c

  日期：——

  13C NMR and mass spectrometry studies have been used to demonstrate that the inhibition of α-chymotrypsin by N-sulfonylhydroxymethylpyrrole inhibitors (10) is non-covalent. Hydroxyalkylpyrroles in which an electron-withdrawing group (acyl substituent) is introduced at the alternative C2 position have been synthesised and also shown to inactivate α-chymotrypsin. SAR studies on this class suggests that the incorporation of phenylalanine at C2 is favoured, however, there is little gain in introducing a hydrophobic substituent at C5.

  13C NMR 和质谱研究已用于证明 N-磺酰羟甲基吡咯抑制剂 (10) 对 α-胰凝乳蛋白酶的抑制是非共价的。已合成了在替代的 C2 位置引入吸电子基团（酰基取代基）的羟基烷基吡咯，并且还显示出可使 α-胰凝乳蛋白酶失活。对此类的 SAR 研究表明，在 C2 处掺入苯丙氨酸是有利的，但在 C5 处引入疏水取代基几乎没有什么好处。
• The Friedel-Crafts Acylation of Ethyl Pyrrole-2-carboxylate. Scope, Limitations, and Application to Synthesis of 7-Substituted Indoles
  作者：Yasuoki Murakami、Masanobu Tani、Takahiro Ariyasu、Chika Nishiyama、Toshiko Watanabe、Yuusaku Yokoyama

  DOI：10.3987/com-88-4616

  日期：——
• New synthesis of pyrrole-2-carboxylic and pyrrole-2,5-dicarboxylic acid esters in the presence of iron-containing catalysts
  作者：R. I. Khusnutdinov、A. R. Baiguzina、R. R. Mukminov、I. V. Akhmetov、I. M. Gubaidullin、S. I. Spivak、U. M. Dzhemilev

  DOI：10.1134/s1070428010070158

  日期：2010.7

  Alkyl 1H-pyrrole-2-carboxylates and dialkyl 1H-pyrrole-2,5-dicarboxylates were synthesized in quantitative yield by reactions of 1H-pyrrole, 2-acetyl-1H-pyrrole, and 1-methyl-1H-pyrrole with carbon tetrachloride and aliphatic alcohols in the presence of iron-containing catalysts. A probable reaction mechanism was proposed, and the rate constants and energies of activation of particular steps were determined on the basis of experimental data.