1-(2-methylphenyl)-3-methyl-1H-pyrrole | 1439384-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-methylphenyl)-3-methyl-1H-pyrrole
• 英文别名: 3-Methyl-1-(2-methylphenyl)pyrrole；3-methyl-1-(2-methylphenyl)pyrrole
• CAS: 1439384-44-7
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: MFHUZMBVDKBQRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  厄多司坦 、 gleinadiene 以 甲醇 为溶剂， 反应 5.0h， 以69%的产率得到1-(2-methylphenyl)-3-methyl-1H-pyrrole
  参考文献：
  名称：

  Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds

  摘要：

  A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp(2) boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp(3) boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. H-1 and B-11 NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition elimination sequence.

  DOI：

  10.1021/acs.joc.5b00593

文献信息

• A novel, efficient synthesis of N-aryl pyrroles via reaction of 1-boronodienes with arylnitroso compounds
  作者：Fabien Tripoteau、Ludovic Eberlin、Mark A. Fox、Bertrand Carboni、Andrew Whiting

  DOI：10.1039/c3cc42227e

  日期：——

  A one-pot hetero-Diels-Alder/ring contraction cascade is presented from the reaction of 1-boronodienes and arylnitroso derivatives to derive N-arylpyrroles in moderate to good yields (up to 82%).

  一锅杂-Diels-Alder /环收缩级联反应是由1-硼二烯与芳基亚硝基衍生物反应以中等至良好的产率（高达82％）衍生出N-芳基吡咯。
• Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds
  作者：Ludovic Eberlin、Bertrand Carboni、Andrew Whiting

  DOI：10.1021/acs.joc.5b00593

  日期：2015.7.2

  A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp(2) boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp(3) boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. H-1 and B-11 NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition elimination sequence.