3-benzoyl-1-(triisopropylsilyl)pyrrole | 90971-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-1-(triisopropylsilyl)pyrrole
• 英文别名: Phenyl[1-[tris(1-methylethyl)silyl]-1H-pyrrol-3-yl]methanone；phenyl-[1-tri(propan-2-yl)silylpyrrol-3-yl]methanone
• CAS: 90971-77-0
• 化学式: C₂₀H₂₉NOSi
• 分子量: 327.542
• InChiKey: VNEOFOQCMZVDIT-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96 °C(Solv: hexane (110-54-3))
• 沸点：
  383.1±15.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1-(triisopropylsilyl)pyrrole 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以98%的产率得到3-苯甲酰吡咯
  参考文献：
  名称：

  Refined Synthesis of 5-Substituted Dipyrromethanes

  摘要：

  DOI：

  10.1021/jo982015+
• 作为产物：
  描述：

  1-(三异丙基甲硅烷基)吡咯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-benzoyl-1-(triisopropylsilyl)pyrrole
  参考文献：
  名称：

  A synthesis of 3-substituted pyrroles through the halogen-metal exchange reaction of 3-bromo-1-(triisopropylsilyl)pyrrole

  摘要：

  DOI：

  10.1021/jo00191a047

文献信息

• N-(Triisopropylsilyl)pyrrole. A progenitor "par excellence" of 3-substituted pyrroles
  作者：Brian L. Bray、Peter H. Mathies、Reto Naef、Dennis R. Solas、Thomas T. Tidwell、Dean R. Artis、Joseph M. Muchowski

  DOI：10.1021/jo00313a019

  日期：1990.12

  A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the alpha-positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the beta-position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields. Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the alpha-positions is decelerated by a factor of > 10(4), vs pyrrole at the same sites, without affecting reactivity at the beta-positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents. This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of beta-substituted pyrroles, many of which would not be directly preparable from 1. TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions. This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound 5.
• BRAY, BRIAN L.;MATHIES, PETER H.;NAEF, RETO;SOLAS, DENNIS R.;TIDWELL, THO+, J. ORG. CHEM., 55,(1990) N6, C. 6317-6328
  作者：BRAY, BRIAN L.、MATHIES, PETER H.、NAEF, RETO、SOLAS, DENNIS R.、TIDWELL, THO+

  DOI：——

  日期：——
• KOZIKOWSKI, A. P.;CHENG, XUE-MIN, J. ORG. CHEM., 1984, 49, N 17, 3239-3240
  作者：KOZIKOWSKI, A. P.、CHENG, XUE-MIN

  DOI：——

  日期：——