2-Isobutyl-6,7-dihydro-4H-pyrano[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester | 180516-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Isobutyl-6,7-dihydro-4H-pyrano[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-(2-methylpropyl)-6,7-dihydro-4H-pyrano[4,3-b]pyrrole-1-carboxylate
• CAS: 180516-74-9
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: YTYXNWIUSGHOAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Isobutyl-6,7-dihydro-4H-pyrano[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以45%的产率得到2-Isobutyl-1,4,6,7-tetrahydro-pyrano[4,3-b]pyrrole
  参考文献：
  名称：

  A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids

  摘要：

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.

  DOI：

  10.1021/jo960401q
• 作为产物：
  描述：

  2-甲基-2-丙基[(2S)-4-甲基-1-氧代-2-戊烷基]氨基甲酸酯 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-Isobutyl-6,7-dihydro-4H-pyrano[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids

  摘要：

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.

  DOI：

  10.1021/jo960401q

文献信息

• A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids
  作者：Pamela Nagafuji、Mark Cushman

  DOI：10.1021/jo960401q

  日期：1996.1.1

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.