bis(N-tert-butoxycarbonyl-5-phenylpyrrol-2-yl )(2,4,6-triisopropylphenyl)borane | 1236292-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: bis(N-tert-butoxycarbonyl-5-phenylpyrrol-2-yl )(2,4,6-triisopropylphenyl)borane
• 英文别名: Tert-butyl 2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]-5-phenylpyrrol-2-yl]-[2,4,6-tri(propan-2-yl)phenyl]boranyl]-5-phenylpyrrole-1-carboxylate；tert-butyl 2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]-5-phenylpyrrol-2-yl]-[2,4,6-tri(propan-2-yl)phenyl]boranyl]-5-phenylpyrrole-1-carboxylate
• CAS: 1236292-78-6
• 化学式: C₄₅H₅₅BN₂O₄
• 分子量: 698.754
• InChiKey: LETRZJAFSIVELI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.08
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(N-tert-butoxycarbonyl-5-phenylpyrrol-2-yl )(2,4,6-triisopropylphenyl)borane 在 BF₃*O(C₂H₅)2 作用下， 以 四氢呋喃 为溶剂， 以13%的产率得到6-phenyl-3-(5-phenylpyrrol-2-yl)-2-(2,4,6-triisopropylphenyl)-1,2-dihydro-1,2-azaborine
  参考文献：
  名称：

  A Study of 1,2-Dihydro-1,2-azaborine in a π-Conjugated System

  摘要：

  The reaction of N-Bac-protected bis(5-phenyl-2-pyrrolyl)borane with BF3 center dot OEt2 produced 3-(phenylpyrrolyl)-6-phenyl- 1,2-dihydro-1,2-azaborine in moderate yield. This compound showed (117 absorption band at a longer wavelength compared to that of its benzene analogue and also exhibited an intense red-shifted fluorescence with a high quantum yield close to unity. According to the X-ray structural analysis, cyclic voltammetry, and theoretical calculations, the 1,2-dihydro-1,2-azaborine acts not like a benzene analogue but like a cyclohexadiene analogue in the extended pi-conjugated skeleton.

  DOI：

  10.1021/om100408m
• 作为产物：
  描述：

  N-boc-2-苯基吡咯 、 2,4,6-三异丙基苯硼酸甲酯 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以58%的产率得到bis(N-tert-butoxycarbonyl-5-phenylpyrrol-2-yl )(2,4,6-triisopropylphenyl)borane
  参考文献：
  名称：

  A Study of 1,2-Dihydro-1,2-azaborine in a π-Conjugated System

  摘要：

  The reaction of N-Bac-protected bis(5-phenyl-2-pyrrolyl)borane with BF3 center dot OEt2 produced 3-(phenylpyrrolyl)-6-phenyl- 1,2-dihydro-1,2-azaborine in moderate yield. This compound showed (117 absorption band at a longer wavelength compared to that of its benzene analogue and also exhibited an intense red-shifted fluorescence with a high quantum yield close to unity. According to the X-ray structural analysis, cyclic voltammetry, and theoretical calculations, the 1,2-dihydro-1,2-azaborine acts not like a benzene analogue but like a cyclohexadiene analogue in the extended pi-conjugated skeleton.

  DOI：

  10.1021/om100408m

文献信息

• A Study of 1,2-Dihydro-1,2-azaborine in a π-Conjugated System
  作者：Takuhiro Taniguchi、Shigehiro Yamaguchi

  DOI：10.1021/om100408m

  日期：2010.11.8

  The reaction of N-Bac-protected bis(5-phenyl-2-pyrrolyl)borane with BF3 center dot OEt2 produced 3-(phenylpyrrolyl)-6-phenyl- 1,2-dihydro-1,2-azaborine in moderate yield. This compound showed (117 absorption band at a longer wavelength compared to that of its benzene analogue and also exhibited an intense red-shifted fluorescence with a high quantum yield close to unity. According to the X-ray structural analysis, cyclic voltammetry, and theoretical calculations, the 1,2-dihydro-1,2-azaborine acts not like a benzene analogue but like a cyclohexadiene analogue in the extended pi-conjugated skeleton.