methyl 3-(4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoate | 774-16-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoate
• 英文别名: 1,5-Dihydro-4-methyl-2-oxopyrrol-3-propionsaeure-methylester；3-(2-methoxycarbonylethyl)-4-methyl-3-pyrrolin-2-one；3-(2-methoxycarbonylethyl)-4-methylpyrrol-2(5H)-one；3-(4-methyl-2-oxo-2,5-dihydro-pyrrol-3-yl)-propionic acid methyl ester；3-(4-Methyl-2-oxo-2,5-dihydro-pyrrol-3-yl)-propionsaeure-methylester；4-Methyl-3-(2-methoxycarbonyl-ethyl)-Δ³-pyrrolon-(2)；methyl 3-(3-methyl-5-oxo-1,2-dihydropyrrol-4-yl)propanoate
• CAS: 774-16-3
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: HWJBWZNFLMYTEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoate 在 硫酸 、 苯甲酰氯 作用下， 以 甲醇 为溶剂， 生成 1,10-dihydro-2-(2-methoxycarbonylethyl)-3,8-dimethyl-1-oxodipyrrin-9-carbaldehyde
  参考文献：
  名称：

  （±）-bonellin二甲基酯的全合成

  摘要：

  已通过外消旋形式通过光化学闭环形成大环的顺序，以外消旋形式合成了具有生理活性的绿色Bon子的绿色色素护角素的二甲基酯。

  DOI：

  10.1039/c39830001237
• 作为产物：
  描述：

  tert-butyl 5-formyl-3-methyl-4-(2-methoxycarbonylethyl)pyrrole-2-carboxylate 在 三乙基硅烷 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 25.17h， 生成 methyl 3-(4-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoate
  参考文献：
  名称：

  与维生素B 12的生物合成研究有关的合成研究。第7部分。（±）-bonellin二甲基酯的合成

  摘要：

  通过合理的光化学途径，以消旋形式合成了绿色海洋颜料即去氧骨蛋白的二甲基酯。该生物活性颜料的两个丙酸酯残基已以差异化形式合成引入，这为合成天然存在的bone骨氨基酸衍生物开辟了道路。

  DOI：

  10.1039/p19880001569

文献信息

• Preparation of pyrrolin-2-ones and 4,5-dihydrodipyrrin-1-ones by oxidation of α-formylpyrroles and α-formyldipyrromethanes with hydrogen peroxide
  作者：Clotilde Pichon-Santander、A.Ian Scott

  DOI：10.1016/s0040-4039(00)00272-0

  日期：2000.4

  Various substituted α-formylpyrroles and -dipyrromethanes have been oxidized by hydrogen peroxide under mild conditions to give pyrrolin-2-ones (2) and 4,5-dihydrodipyrrin-1-ones (4) with concomitant loss of the formyl substituent, thus extending the scope of this oxidation to dipyrromethanes. This makes the reaction especially useful for the preparation of bile pigments, for which the pyrrolinones

  在温和的条件下，过氧化氢已氧化了各种取代的α-甲酰基吡咯和-dipyrroro甲烷，生成了吡咯烷-2-酮（2）和4,5-二氢联吡啶-1-酮（4），同时甲酰基取代基也因此丢失，从而扩展了氧化为二吡咯甲烷的范围。这使得该反应对于胆汁颜料的制备特别有用，对于该胆汁颜料，吡咯烷酮和4，5-二氢二吡咯烷酮构成重要的合成子。
• Stepwise synthesis of symmetrically substituted azaporphyrins
  作者：Claudia M. Müller、Franz-Peter Montforts

  DOI：10.1142/s1088424614500175

  日期：2014.5

  Porphyrins that have one nitrogen atom instead of a methine bridge at the meso-position are named monoazaporphyrin. This class of porphyrinoid compounds though first investigated by Fischer in the thirties of the last century is still less common compared to other porphyrin derivatives. We describe here a concise convergent synthetic route leading to a symmetric azaporphyrin 7a and its zinc compex 22.

  在中位有一个氮原子而不是甲桥的卟啉被命名为单氮卟啉。这一类卟啉化合物虽然在上世纪 30 年代就由费舍尔首次研究，但与其他卟啉衍生物相比，仍然不太常见。我们在此介绍一条简明的聚合路线，通过它可以得到对称氮杂卟啉 7a 及其锌合物 22。
• Synthesis and properties of mesobilirubins XIIγ and XIIIγ and their mesobiliverdins
  作者：Portia Mahal G. Sabido、David A. Lightner

  DOI：10.1007/s00706-014-1160-6

  日期：2014.5

  The title pigments, with propionic acid groups displaced to the lactam end rings, were synthesized for the first time by the "1 + 2 + 1" approach, coupling two equivalents of a monopyrrole to a dipyrrylmethane (to give XII gamma), or the "2 + 2" approach, self-coupling two equivalents of a dipyrrinone (to give XIII gamma). Using the "1 + 2 + 1" approach, mesobilirubin III alpha was also prepared. Mesobilirubins XII gamma and XIII gamma are more polar than mesobilirubin III alpha and unlike III alpha cannot effectively engage the propionic acid groups in intramolecular hydrogen bonding to the dipyrrinone components. The new mesobilirubins give exciton coupled circular dichroism spectra in the presence of human serum albumin or quinine, with the XII gamma isomer exhibiting Cotton effect intensities nearly as strong as those from the III alpha isomer; whereas, the XIII gamma isomer exhibits far weaker intensities. Mesobilirubin III alpha requires glucuronidation for hepatobiliary elimination; whereas, XII gamma and XIII gamma do not, and they are excreted intact across the liver into bile. The corresponding biliverdins XII gamma and XIII gamma are reduced only slowly by biliverdin IX alpha reductase, in contrast to the fast reduction of the natural IX alpha isomer.
• Plieninger; Decker, Justus Liebigs Annalen der Chemie, 1956, vol. 598, p. 198,205
  作者：Plieninger、Decker

  DOI：——

  日期：——
• Montforts, Franz-Peter; Schwartz, Ulrich Manfred, Liebigs Annalen der Chemie, 1991, # 8, p. 709 - 726
  作者：Montforts, Franz-Peter、Schwartz, Ulrich Manfred

  DOI：——

  日期：——