2-Phenylindolizine-1,3-dicarbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Phenylindolizine-1,3-dicarbaldehyde
• 化学式: C₁₆H₁₁NO₂
• mdl: MFCD02934907
• 分子量: 249.269
• InChiKey: AJGYDURVFFIHQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Phenylindolizine-1,3-dicarbaldehyde 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Regiospecific Synthesis of 1-(3,4-Dihydro-2H-benzo[b][1,4]oxazin-3-yl)indolizine Derivatives Through a Three-step Sequence from 2-Arylindolizine

  摘要：

  A three-step sequence for the synthesis of new indolizine derivatives containing 1,4-benzoxazine subunits is presented. Two formyl groups were firstly introduced into 2-arylindolizine via Vilsmeier-Haack reaction. Subsequent aldimine condensation gave regiospecific indolizin-1-imine product, which underwent DMAP-catalyzed cascade reaction with alpha-bromoketones, giving 1-(3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)indolizine derivatives in moderate to good yields. A wide range of substrates were tolerated in this reaction. The mechanism for DMAP-catalyzed process was briefly discussed with a tentative catalytic cycle proposed.

  DOI：

  10.3987/com-18-13982
• 作为产物：
  描述：

  2-苯基吲哚嗪 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 水 、 sodium acetate 作用下， 反应 8.0h， 生成 2-Phenylindolizine-1,3-dicarbaldehyde
  参考文献：
  名称：

  Regiospecific Synthesis of 1-(3,4-Dihydro-2H-benzo[b][1,4]oxazin-3-yl)indolizine Derivatives Through a Three-step Sequence from 2-Arylindolizine

  摘要：

  A three-step sequence for the synthesis of new indolizine derivatives containing 1,4-benzoxazine subunits is presented. Two formyl groups were firstly introduced into 2-arylindolizine via Vilsmeier-Haack reaction. Subsequent aldimine condensation gave regiospecific indolizin-1-imine product, which underwent DMAP-catalyzed cascade reaction with alpha-bromoketones, giving 1-(3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)indolizine derivatives in moderate to good yields. A wide range of substrates were tolerated in this reaction. The mechanism for DMAP-catalyzed process was briefly discussed with a tentative catalytic cycle proposed.

  DOI：

  10.3987/com-18-13982

文献信息

• Regiospecific Synthesis of 1-(3,4-Dihydro-2H-benzo[b][1,4]oxazin-3-yl)indolizine Derivatives Through a Three-step Sequence from 2-Arylindolizine
  作者：Yongjia Shang、Min Zhang、Xinwei He、Shanqing Li

  DOI：10.3987/com-18-13982

  日期：——

  A three-step sequence for the synthesis of new indolizine derivatives containing 1,4-benzoxazine subunits is presented. Two formyl groups were firstly introduced into 2-arylindolizine via Vilsmeier-Haack reaction. Subsequent aldimine condensation gave regiospecific indolizin-1-imine product, which underwent DMAP-catalyzed cascade reaction with alpha-bromoketones, giving 1-(3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)indolizine derivatives in moderate to good yields. A wide range of substrates were tolerated in this reaction. The mechanism for DMAP-catalyzed process was briefly discussed with a tentative catalytic cycle proposed.