4-tert-butyl-5-(3-tert-butyl-5-carboxy-4-methyl-1H-pyrrol-2-yl)-3-methyl-1H-pyrrole-2-carboxylic acid | 639786-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-tert-butyl-5-(3-tert-butyl-5-carboxy-4-methyl-1H-pyrrol-2-yl)-3-methyl-1H-pyrrole-2-carboxylic acid
• CAS: 639786-25-7
• 化学式: C₂₀H₂₈N₂O₄
• 分子量: 360.453
• InChiKey: NRUFVZXFPHUFBC-UHFFFAOYSA-N

物化性质

• 沸点：
  594.7±50.0 °C(predicted)
• 密度：
  1.192±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-(-)-2-甲基-1-丁醇 、 4-tert-butyl-5-(3-tert-butyl-5-carboxy-4-methyl-1H-pyrrol-2-yl)-3-methyl-1H-pyrrole-2-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 、 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到
  参考文献：
  名称：

  Synthesis of a Chiral 3,3?-Di- tert -butyl-2,2?-bipyrrole

  摘要：

  Diethyl 3,3'-di-tert-butyl-4,4'-dimethyl-2,2'-bipyrrole-5,5'-dicarboxylate was synthesized in four steps from ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate. The CH2 hydrogens of the ethyl ester groups of the former are diastereotopic in the H-1-NMR, consistent with axial chirality of the bipyrrole and restricted rotation about the 2,2-bipyrrole bond, due to the tert-butyl groups. An X-ray structure of the crystalline target compound shows the pyrrole rings are twisted out of coplanarity by 84.5degrees.

  DOI：

  10.1007/s00706-002-0562-z
• 作为产物：
  描述：

  3,5-二甲基-1H-吡咯-2-甲酸乙酯 在 sodium hydroxide 、 磺酰氯 、 硫酸 、 碘 、 铜 、 碳酸氢钠 、 potassium iodide 作用下， 以 乙醚 、 硝基甲烷 、 乙醇 、 水 、 xylene 为溶剂， 反应 76.75h， 生成 4-tert-butyl-5-(3-tert-butyl-5-carboxy-4-methyl-1H-pyrrol-2-yl)-3-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of a Chiral 3,3?-Di- tert -butyl-2,2?-bipyrrole

  摘要：

  Diethyl 3,3'-di-tert-butyl-4,4'-dimethyl-2,2'-bipyrrole-5,5'-dicarboxylate was synthesized in four steps from ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate. The CH2 hydrogens of the ethyl ester groups of the former are diastereotopic in the H-1-NMR, consistent with axial chirality of the bipyrrole and restricted rotation about the 2,2-bipyrrole bond, due to the tert-butyl groups. An X-ray structure of the crystalline target compound shows the pyrrole rings are twisted out of coplanarity by 84.5degrees.

  DOI：

  10.1007/s00706-002-0562-z

文献信息

• Synthesis of a Chiral 3,3?-Di- tert -butyl-2,2?-bipyrrole
  作者：Pawel Skowronek、David A. Lightner

  DOI：10.1007/s00706-002-0562-z

  日期：2003.5.1

  Diethyl 3,3'-di-tert-butyl-4,4'-dimethyl-2,2'-bipyrrole-5,5'-dicarboxylate was synthesized in four steps from ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate. The CH2 hydrogens of the ethyl ester groups of the former are diastereotopic in the H-1-NMR, consistent with axial chirality of the bipyrrole and restricted rotation about the 2,2-bipyrrole bond, due to the tert-butyl groups. An X-ray structure of the crystalline target compound shows the pyrrole rings are twisted out of coplanarity by 84.5degrees.