1-(dimethyl-t-butylsilyl)-2,5-dimethylpyrrole | 108939-95-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(dimethyl-t-butylsilyl)-2,5-dimethylpyrrole
• 英文别名: tert-butyl-(2,5-dimethylpyrrol-1-yl)-dimethylsilane
• CAS: 108939-95-3
• 化学式: C₁₂H₂₃NSi
• 分子量: 209.407
• InChiKey: LKFZOMXHRFAPPK-UHFFFAOYSA-N

物化性质

• 沸点：
  124 °C(Press: 14 Torr)
• 密度：
  0.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  、 1-(dimethyl-t-butylsilyl)-2,5-dimethylpyrrole 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 sodium hydride 作用下， 以 氯仿 、 mineral oil 为溶剂， 以50 %的产率得到1-(tert-butyldimethylsilyl)-2,5-dimethyl-3-(1,1,1-trifluoro-4-phenylbut-3-en-2-yl)-1H-pyrrole
  参考文献：
  名称：

  Controllable Skeletal and Peripheral Editing of Pyrroles with Vinylcarbenes

  摘要：

  The skeletal editing of azaarenes through insertion, deletion, or swapping of single atoms has recently gained considerable momentum in chemical synthesis. Here, we describe a practical skeletal editing strategy using vinylcarbenes in‐situ generated from trifluoromethyl vinyl N‐triftosylhydrazones, leading to the first dearomative skeletal editing of pyrroles through carbon‐atom insertion. Furthermore, depending on the used catalyst and substrate, three types of peripheral editing reactions of pyrroles are also disclosed: α‐ or γ‐selective C–H insertion, and [3+2] cycloaddition. These controllable molecular editing reactions provide a powerful platform for accessing medicinally relevant CF3‐containing N‐heterocyclic frameworks, such as 2,5‐dihydropyridines, piperidines, azabicyclo[3.3.0]octadienes, and allylated pyrroles from readily available pyrroles. Mechanistic insights from experiments and density functional theory (DFT) calculations shed light on the origin of substrate‐ or catalyst‐controlled chemo‐ and regioselectivity as well as the reaction mechanism.

  DOI：

  10.1002/anie.202401359
• 作为产物：
  描述：

  2,5-二甲基吡咯 、 叔丁基二甲基氯硅烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成 1-(dimethyl-t-butylsilyl)-2,5-dimethylpyrrole
  参考文献：
  名称：

  Controllable Skeletal and Peripheral Editing of Pyrroles with Vinylcarbenes

  摘要：

  The skeletal editing of azaarenes through insertion, deletion, or swapping of single atoms has recently gained considerable momentum in chemical synthesis. Here, we describe a practical skeletal editing strategy using vinylcarbenes in‐situ generated from trifluoromethyl vinyl N‐triftosylhydrazones, leading to the first dearomative skeletal editing of pyrroles through carbon‐atom insertion. Furthermore, depending on the used catalyst and substrate, three types of peripheral editing reactions of pyrroles are also disclosed: α‐ or γ‐selective C–H insertion, and [3+2] cycloaddition. These controllable molecular editing reactions provide a powerful platform for accessing medicinally relevant CF3‐containing N‐heterocyclic frameworks, such as 2,5‐dihydropyridines, piperidines, azabicyclo[3.3.0]octadienes, and allylated pyrroles from readily available pyrroles. Mechanistic insights from experiments and density functional theory (DFT) calculations shed light on the origin of substrate‐ or catalyst‐controlled chemo‐ and regioselectivity as well as the reaction mechanism.

  DOI：

  10.1002/anie.202401359

文献信息

• Dhanak, Dashyant; Reese, Colin B., Journal of the Chemical Society. Perkin transactions I, 1986, p. 2181 - 2186
  作者：Dhanak, Dashyant、Reese, Colin B.

  DOI：——

  日期：——
• DHANAK D.; REESE C. B., J. CHEM. SOC. PERKIN TRANS.,(1986) N 12, 2181-2186
  作者：DHANAK D.、 REESE C. B.

  DOI：——

  日期：——