3-benzoyl-1-(tert-butoxycarbonyl)-4-phenylpyrrole | 211742-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-1-(tert-butoxycarbonyl)-4-phenylpyrrole
• 英文别名: Tert-butyl 3-benzoyl-4-phenylpyrrole-1-carboxylate
• CAS: 211742-03-9
• 化学式: C₂₂H₂₁NO₃
• 分子量: 347.414
• InChiKey: UUJHCNUDOWPCBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C
• 沸点：
  522.978±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.100±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1-(tert-butoxycarbonyl)-4-phenylpyrrole 在 2,2,6,6-四甲基哌啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三甲基氯化锡 作用下， 生成 3-benzoyl-2-bromo-1-(tert-butoxycarbonyl)-4-phenylpyrrole
  参考文献：
  名称：

  A Direct Synthesis of 2-(Trimethylstannyl)pyrroles from Michael Acceptors and Stannylated Tosylmethyl Isocyanide¹

  摘要：

  A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized efficiently by a base-induced reaction of stannylated TosMIC with Michael accepters. Stills cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo coupling reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.

  DOI：

  10.1021/jo972216y
• 作为产物：
  描述：

  反式-查耳酮 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 3-benzoyl-1-(tert-butoxycarbonyl)-4-phenylpyrrole
  参考文献：
  名称：

  A Direct Synthesis of 2-(Trimethylstannyl)pyrroles from Michael Acceptors and Stannylated Tosylmethyl Isocyanide¹

  摘要：

  A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized efficiently by a base-induced reaction of stannylated TosMIC with Michael accepters. Stills cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo coupling reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.

  DOI：

  10.1021/jo972216y

文献信息

• A Direct Synthesis of 2-(Trimethylstannyl)pyrroles from Michael Acceptors and Stannylated Tosylmethyl Isocyanide¹
  作者：Harm P. Dijkstra、Ronald ten Have、Albert M. van Leusen

  DOI：10.1021/jo972216y

  日期：1998.8.1

  A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized efficiently by a base-induced reaction of stannylated TosMIC with Michael accepters. Stills cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo coupling reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.