3-tert-butoxycarbonyl-1,2-dimethyl-4,9-dihydropyrrolo[2,1-b]quinazoline | 1258407-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-tert-butoxycarbonyl-1,2-dimethyl-4,9-dihydropyrrolo[2,1-b]quinazoline
• 英文别名: Tert-butyl 1,2-dimethyl-4,9-dihydropyrrolo[2,1-b]quinazoline-3-carboxylate
• CAS: 1258407-80-5
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: HTOHSYGGQVIZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-tert-butoxycarbonyl-1,2-dimethyl-4,9-dihydropyrrolo[2,1-b]quinazoline 在 air 作用下， 以 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 288.0h， 以70%的产率得到Tert-butyl 7-hydroxy-6,7-dimethyl-5-oxa-2,8-diazatetracyclo[8.4.0.03,8.04,6]tetradeca-1(14),2,10,12-tetraene-4-carboxylate
  参考文献：
  名称：

  Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions

  摘要：

  A pyrrolo[2,1-b]quinazoline has been found to undergo both epoxidation and hydroxylation on the pyrrole nucleus upon simple exposure of an acetone solution to air or oxygen. The oxygenation reaction occurs most readily when the starting compound contains a t-butyl ester at the 3-position, compared to a cyano or phenylsulfonyl. The structure of the product has been confirmed by X-ray crystal analysis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.073
• 作为产物：
  描述：

  邻溴苄胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙醇 、 叔丁醇 为溶剂， 反应 6.0h， 生成 3-tert-butoxycarbonyl-1,2-dimethyl-4,9-dihydropyrrolo[2,1-b]quinazoline
  参考文献：
  名称：

  An intramolecular N-arylation approach to 3-functionalized 4,9-dihydropyrrolo[2,1-b]quinazolines

  摘要：

  AbstractA series of 4,9‐dihydropyrrolo[2,1‐b]quinazolines containing electron withdrawing groups at the 3‐position have been prepared by the palladium‐catalyzed intramolecular N‐arylation of some 2‐aminopyrroles having a 2‐bromobenzyl group at the N‐1 position. Important for success of the reaction is the use of X‐phos, a biphenyl mono‐phosphine ligand, instead of xantphos, a more standard diphosphine ligand, and the use of t‐BuOH as reaction solvent. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.534

文献信息

• An intramolecular N-arylation approach to 3-functionalized 4,9-dihydropyrrolo[2,1-b]quinazolines
  作者：Nisaraporn Suthiwangcharoen、Steven M. Pochini、Daniel P. Sweat、Chad E. Stephens

  DOI：10.1002/jhet.534

  日期：2011.5

  AbstractA series of 4,9‐dihydropyrrolo[2,1‐b]quinazolines containing electron withdrawing groups at the 3‐position have been prepared by the palladium‐catalyzed intramolecular N‐arylation of some 2‐aminopyrroles having a 2‐bromobenzyl group at the N‐1 position. Important for success of the reaction is the use of X‐phos, a biphenyl mono‐phosphine ligand, instead of xantphos, a more standard diphosphine ligand, and the use of t‐BuOH as reaction solvent. J. Heterocyclic Chem., (2011).
• Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions
  作者：Ryan A. Hawkins、Chad E. Stephens

  DOI：10.1016/j.tetlet.2010.09.073

  日期：2010.11

  A pyrrolo[2,1-b]quinazoline has been found to undergo both epoxidation and hydroxylation on the pyrrole nucleus upon simple exposure of an acetone solution to air or oxygen. The oxygenation reaction occurs most readily when the starting compound contains a t-butyl ester at the 3-position, compared to a cyano or phenylsulfonyl. The structure of the product has been confirmed by X-ray crystal analysis. (C) 2010 Elsevier Ltd. All rights reserved.