3-(4,5-dihydro-4-methylpyrrolo[1,2-a]quinoxalin-4-yl)-2-phenylpropan-1-ol | 1176666-97-9

• 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-(4,5-dihydro-4-methylpyrrolo[1,2-a]quinoxalin-4-yl)-2-phenylpropan-1-ol
• 英文别名: 3-(4-methyl-5H-pyrrolo[1,2-a]quinoxalin-4-yl)-2-phenylpropan-1-ol
• CAS: 1176666-97-9
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: SVUSKZUMHVPYFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-氨基苯基)吡咯 、 2-phenyl-4-pentyn-1-ol 在 platinum(II) bromde 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以93%的产率得到3-(4,5-dihydro-4-methylpyrrolo[1,2-a]quinoxalin-4-yl)-2-phenylpropan-1-ol
  参考文献：
  名称：

  Platinum-Catalyzed Formal Markownikoff’s Hydroamination/Hydroarylation Cascade of Terminal Alkynes Assisted by Tethered Hydroxyl Groups

  摘要：

  An efficient method for Markownikoff's hydroamination-hydroarylation of alkynols using PtBr2 as catalyst has been developed. The platinum-catalyzed reactions of alkynols with amino group containing aromatics were achieved in methanol over a reaction time of 6-24 h and temperature ranging from rt to 80 degrees C. This method works well for a variety of alkynols and aromatic amino compounds to give substituted pyrrolo[1,2-a]quinoxalines and indolo[3,2-c]quinolines in good to excellent yields.

  DOI：

  10.1021/jo901200j

文献信息

• Pt(IV)-Catalyzed Hydroamination Triggered Cyclization: A Strategy to Fused Pyrrolo[1,2-<i>a</i>]quinoxalines, Indolo[1,2-<i>a</i>]quinoxalines, and Indolo[3,2-<i>c</i>]quinolines
  作者：Nitin T. Patil、Rahul D. Kavthe、Valmik S. Shinde、Balasubramanian Sridhar

  DOI：10.1021/jo100373w

  日期：2010.5.21

  A PtCl4-catalyzed hydroamination-triggered cyclization strategy to access biologically interesting N-containing heterocycles such as pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, and indolo[3,2-c]quinolines is described. The reaction makes use of aminoaromatics such as 1-(2-aminophenyl)pyrroles, N-(2-aminophenyl)indoles, 2-(2-aminophenyl)indoles, and alkynes having a tethered hydroxyl group

  一种PtCl 4催化的加氢胺触发的环化策略，以获取生物学上有趣的含N杂环，如吡咯并[1,2- a ]喹喔啉，吲哚[1,2- a ]喹喔啉和吲哚[3,2- c ]喹啉描述。该反应利用氨基芳族化合物，例如1-（2-氨基苯基）吲哚，N-（2-氨基苯基）吲哚，2-（2-氨基苯基）吲哚和具有束缚羟基的炔烃。从机理上讲，该反应非常吸引人，因为它涉及由单一金属催化剂PtCl 4催化的多个催化循环。当反应在微波辅助条件下进行时，我们观察到了速率的显着提高。
• Platinum-Catalyzed Formal Markownikoff’s Hydroamination/Hydroarylation Cascade of Terminal Alkynes Assisted by Tethered Hydroxyl Groups
  作者：Nitin T. Patil、Rahul D. Kavthe、Vivek S. Raut、Vaddu V. N. Reddy

  DOI：10.1021/jo901200j

  日期：2009.8.21

  An efficient method for Markownikoff's hydroamination-hydroarylation of alkynols using PtBr2 as catalyst has been developed. The platinum-catalyzed reactions of alkynols with amino group containing aromatics were achieved in methanol over a reaction time of 6-24 h and temperature ranging from rt to 80 degrees C. This method works well for a variety of alkynols and aromatic amino compounds to give substituted pyrrolo[1,2-a]quinoxalines and indolo[3,2-c]quinolines in good to excellent yields.