Methyl 4-methyl-2-pyrrol-1-ylpentanoate | 86436-65-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 4-methyl-2-pyrrol-1-ylpentanoate
• CAS: 86436-65-9
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: VPOWNZZBOJLXPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 4-methyl-2-pyrrol-1-ylpentanoate 在 sodium hydroxide 、 四氯化钛 作用下， 以 甲醇 为溶剂， 反应 5.17h， 生成 2-(2-formylpyrrol-1-yl)-4-methylpentanoic acid
  参考文献：
  名称：

  1,4-Dichloro-1,4-dimethoxybutane as a mild reagent for the conversion of primary amines to pyrroles. Synthesis of a pyrrole compound from tobacco

  摘要：

  DOI：

  10.1021/jo00166a025
• 作为产物：
  描述：

  Methyl 2-(2,5-dihydropyrrol-1-yl)-4-methylpentanoate 在 Aspergillus niger monoamine oxidase variant D₅ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Methyl 4-methyl-2-pyrrol-1-ylpentanoate
  参考文献：
  名称：

  Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

  摘要：

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.

  DOI：

  10.1021/acscatal.6b03081

文献信息

• Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles
  作者：Nicoló Scalacci、Gary W. Black、Giulio Mattedi、Nicola L. Brown、Nicholas J. Turner、Daniele Castagnolo

  DOI：10.1021/acscatal.6b03081

  日期：2017.2.3

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.
• 1,4-Dichloro-1,4-dimethoxybutane as a mild reagent for the conversion of primary amines to pyrroles. Synthesis of a pyrrole compound from tobacco
  作者：T. H. Chan、S. D. Lee

  DOI：10.1021/jo00166a025

  日期：1983.9