ethyl 5-formyl-3-(2-ethoxycarbonyl)ethyl-4-methyl-1H-pyrrole-2-carboxylate | 52091-03-9

• 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 5-formyl-3-(2-ethoxycarbonyl)ethyl-4-methyl-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 5-formyl-4-methyl-3-(2-ethoxycarbonylethyl)pyrrole-2-carboxylate；ethyl 2-formyl-3-methyl-5-(ethoxycarbonyl)-1H-pyrrole-4-propanoate；ethyl 3-(2-carbethoxy-5-formyl-4-methyl-1H-3-pyrrolyl)propanoate；ethyl 5-carboethoxy-2-formyl-3-methyl-1H-pyrrole-4-propanoate；3-(2-ethoxycarbonyl-ethyl)-5-formyl-4-methyl-pyrrole-2-carboxylic acid ethyl ester；ethyl 3-(3-ethoxy-3-oxopropyl)-5-formyl-4-methyl-1H-pyrrole-2-carboxylate
• CAS: 52091-03-9
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: RIRUOTVJPURMME-UHFFFAOYSA-N

物化性质

• 沸点：
  445.3±45.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-formyl-3-(2-ethoxycarbonyl)ethyl-4-methyl-1H-pyrrole-2-carboxylate 在 硫酸 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2-ylidene)methyl]-4-methyl-(Z)-1H-pyrrole-3-propionic acid methyl ester
  参考文献：
  名称：

  （mn）-高红素：合成与结构

  摘要：

  摘要合成了五个新的胆红素高红素类似物，它们的两个二吡啶酮成分与（CH 2）2，（CH 2）3和（CH 2）4单元相连，丙酸链缩短为乙酸，延长为丁酸，并通过光谱法进行了研究和分子力学计算，以确定形成构象的氢键的能力。m表示连接的CH 2单元数，n表示链烷酸链的CH 2单元数（mn制备了（-），（2.1）-，（3.2）-，（4.2）-和（4.3）-山红蛋白，并与先前合成的（2.2）和（2.3）进行了比较，后者在CHCl 3中采用了分子内氢键构象。 图形概要

  DOI：

  10.1007/s00706-014-1288-4
• 作为产物：
  描述：

  ethyl 4,5-dimethyl-3-(2-ethoxycarbonylethyl)pyrrole-2-carboxylate 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以87%的产率得到ethyl 5-formyl-3-(2-ethoxycarbonyl)ethyl-4-methyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  一种廉价的，选​​择性的将α-甲基氧化为α-甲酰基吡咯烷的方法

  摘要：

  在含水甲醇中，溴酸钠可将α-甲基吡咯转化为α-甲酰基。加入1％硝酸铈铵作为助氧化剂，可使合成有用的2-甲酰基吡咯2a-d的分离产率提高至约70％，或接近仅使用昂贵得多的硝酸铈铵作为氧化剂时的产率。

  DOI：

  10.1002/jhet.5570380531

文献信息

• 10-Thia-mesobilirubin-xiiiα
  作者：Brahmananda Ghosh、David A. Lightner

  DOI：10.1002/jhet.5570400624

  日期：2003.11

  The 10-thia analog of mesobilirubin-XIIIα, with the central C(10) CH2 group replaced by sulfur (1a) was synthesized by condensation of neoxanthobilirubic acid (3) with sulfur dichloride. Thia-rubin 1a is a brilliant yellow solid, forming bright yellow solutions with uv-visible absorption maximum from 425–440 nm.

  通过新黄胆酸（3）与二氯化硫的缩合反应合成了10-硫杂的中胆红素-XIIIα，其中央C（10）CH 2基团被硫（1a）取代。Thia-rubin 1a是一种亮黄色固体，形成亮黄色溶液，在425-440 nm范围内具有最大的uv可见吸收。
• A New Class of Linear Tetrapyrroles:  Acetylenic 10,10a-Didehydro-10a-homobilirubins
  作者：Bin Tu、Brahmananda Ghosh、David A. Lightner

  DOI：10.1021/jo030252t

  日期：2003.11.1

  Novel bilirubin analogues with dipyrrinones conjoined to an acetylene rather than a methylene group were synthesized and examined spectroscopically. Despite the increased separation of the dipyrrinones forced by replacing a -CH2- by a -Cequivalent toC- unit, molecular dynamics calculations show that, like bilirubin, they may still engage in intramolecular hydrogen bonding to carboxylic acid groups when the propionic acid chains are slightly lengthened, e.g., butanoic acids. Unlike bilirubin, however, which is bent in the middle and has a ridge-tile shape, the acetylene orients the attached dipyrrinones along a linear path, and intramolecular hydrogen bonding preserves a twisted linear molecular shape. The extended planes of the dipyrrinones intersect along the -Cequivalent toC- axis at an angle of 136degrees for the conformation stabilized by intramolecular hydrogen bonding in the bis-butyric acid rubin (1b). With shorter acid chains (propionic), only one CO2H can engage an opposing dipyrrinone in intramolecular hydrogen bonding, and in this energy-minimum conformation of the linear pigment la, the intersection of the extended planes of the dipyrrinones has an angle of 171degrees. Spectroscopic evidence for such linearized and twisted structures was found in the pigments' NMR spectral data and their exciton UV-vis and induced circular dichroism spectra.
• 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.
• Synthesis and properties of C(10) isopropyl and isopropylidene analogs of bilirubin
  作者：Ari K. Kar、David A. Lightner

  DOI：10.1016/s0040-4020(98)00254-3

  日期：1998.5

  Analogs of bilirubin with isopropyl (1) and isopropylidene (2) groups attached to the central C(10) carbon were synthesized and evaluated by a combination of NMR, UV-vis and circular dichroism spectroscopy and molecular dynamics calculations. These methods and H-1H-1}-homonuclear Overhauser effect (NOE) experiments in CDCl3 solutions indicate that the rubins' carboxylic acid groups are tethered to the dipyrrinone lactams and/or pyrroles by intramolecular hydrogen bonds and confirm that the pigments adopt a folded, ridge-tile shape in solution. (C) 1998 Elsevier Science Ltd. All rights reserved.