ethyl 4<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate | 99017-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate
• 英文别名: 3,5-dimethyl-2-(ethoxycarbonyl)-1H-pyrrole-4-ethanoic acid methyl ester；ethyl 3,5-dimethyl-4-(methoxycarbonyl)-methyl-1H-pyrrole-2-carboxylate；ethyl 3,5-dimethyl-4-(methoxycarbonyl)methyl-1H-pyrrole-2-carboxylate；Ethyl 4-(2-methoxy-2-oxoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 99017-93-3
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: VBKDJBWIBPLHCD-UHFFFAOYSA-N

物化性质

• 熔点：
  122.5-124 °C
• 沸点：
  360.8±42.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  6
• 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：

  ethyl 4<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 methyl 2-(5-(6-(2-methoxy-2-oxoethyl)-1,1,3,5,7-pentamethyl-2,3-dihydro-1H-pyrrolizin-3-yl)-2,4-dimethyl-1H-pyrrol-3-yl)acetate
  参考文献：
  名称：

  一锅合成不对称环状双吡咯

  摘要：

  活化的官能化吡咯与丙酮的缩合导致不对称的双（吡咯），其通过环环化形成。该方法在某种程度上是通用的，并且可以应用于各种酮，以及不与吡咯环直接相邻的不带有吸电子基团的一系列吡咯底物。

  DOI：

  10.1021/ol202457n
• 作为产物：
  描述：

  氨基丙二酸二乙酯 、 3,3-二乙酰基丙酸甲酯 在 溶剂黄146 作用下， 以75%的产率得到ethyl 4<(methoxycarbonyl)methyl>-3,5-dimethylpyrrole-2-carboxylate
  参考文献：
  名称：

  Pyrrole chemistry. An improved synthesis of ethyl pyrrole-2-carboxylate esters from diethyl aminomalonate

  摘要：

  DOI：

  10.1021/jo00350a033

文献信息

• Synthesis and properties of homomologated and contracted dipyrrinone analogs of xanthobilirubic acid
  作者：Gisbert Puzicha、David P. Shrout、David A. Lightner

  DOI：10.1002/jhet.5570270749

  日期：1990.11

  Dipyrrinone analogs of xanthobilirubic acid, 5-[1,5-didehydro-3-ethyl-4-methyl-5-oxo-2H-pyrrol-2-ylidene)-methyl]-2,4-dimethyl-1H-pyrrol-3-propanoic acid, with alkanoic acid chain lengths varying from formic to caproic have been synthesized as their methyl esters and characterized spectroscopically. All of the dipyrrinones studied exhibit intermolecular hydrogen bonding in chloroform, as detected by

  黄胆红酸的双吡喃酮类似物5- [1,5-didehydro-3-乙基-4-甲基-5-oxo-2 H-吡咯-2-亚甲基）-甲基] -2,4-二甲基-1 H-吡咯链烷酸链长从甲酸到己酸不等的-3-丙酸已被合成为它们的甲酯，并进行了光谱表征。通过1 H-nmr检测，所有研究的二吡啶酮均在氯仿中表现出分子间氢键，并且羧基对uv可见光谱的影响随链长的增加而降低。
• Stable 4E-dipyrrinones
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1016/s0040-4020(99)00617-1

  日期：1999.9

  Dipyrrinones formed by DBU and n-Bu3P-promoted condensation of 5-p-toluene-sulfonylpyrrolinones with pyrrole 2-aldehydes, gave high yields of product with predominantly the E-configuration when the aldehyde had a 5-carboethoxy group. The 4E-dipyrrinones were readily purified by chromatography and were stable in solutions shielded from light. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A Water-Soluble Synthetic Bilirubin with Carboxyl Groups Replaced by Sulfonyl Moieties
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1007/s007060170035

  日期：2001.10

  The first symmetrical bilirubin analog with CO2H groups replaced by SO3H, 8,12-bis-(2-sulfo-ethyl)-3,17-diethyl-2,7,13,18-tetramethyl-(10H,21H,23H,24H)-bilin-1,19-dione, was synthesized from methyl (2,4-dimethyl-5-ethoxycarbonyl-1H-pyrrol-3-yl) acetate in nine steps via the sulfonic acid analog of xanthobilirubic acid (XBR) and isolated as its disodium salt. The sulfonic acid group was introduced at an early stage of the synthesis by reaction of an intermediate, ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate, with sodium sulfite. The disodium bilirubin disulfonate exhibits NMR spectroscopic properties rather similar to those of the parent carboxylic acid, mesobilirubin-XIII alpha; however, its UV/Vis spectra are blue-shifted and broadened relative to those of the parent compound. Like mesobilirubin, the disulfonate displays-a positive exciton chirality circular dichroism spectrum, albeit with weaker Cotton effects, in a buffered aqueous solution (pH = 7.4) containing a 2:1 molar ratio of human serum albumin.
• PAINE, J. B. III;DOLPHIN, D., J. ORG. CHEM., 1985, 50, N 25, 5598-5604
  作者：PAINE, J. B. III、DOLPHIN, D.

  DOI：——

  日期：——
• One-Pot Synthesis of Asymmetric Annulated Bis(pyrrole)s
  作者：Deborah A. Smithen、T. Stanley Cameron、Alison Thompson

  DOI：10.1021/ol202457n

  日期：2011.11.4

  Condensation of activated functionalized pyrroles with acetone results in asymmetric bis(pyrrole)s, formed via ring annulation. The methodology is somewhat general and can be applied to a variety of ketones, as well as to a range of pyrrolic substrates that do not bear electron-withdrawing groups directly adjacent to the pyrrole ring.

  活化的官能化吡咯与丙酮的缩合导致不对称的双（吡咯），其通过环环化形成。该方法在某种程度上是通用的，并且可以应用于各种酮，以及不与吡咯环直接相邻的不带有吸电子基团的一系列吡咯底物。