5-Azido-1-(cyclohexen-1-yl)-2-methylidenepentan-1-one | 929296-01-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Azido-1-(cyclohexen-1-yl)-2-methylidenepentan-1-one
• CAS: 929296-01-5
• 化学式: C₁₂H₁₇N₃O
• 分子量: 219.286
• InChiKey: BBXOSRRWEMCVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Azido-1-(cyclohexen-1-yl)-2-methylidenepentan-1-one 在 palladium on activated charcoal air 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成
  参考文献：
  名称：

  Intramolecular Azide Trapping of the Nazarov Intermediate:  Formation of Peroxy-Bridged Indolizidinones via a Deep-Seated Rearrangement and Aerobic Oxidation

  摘要：

  Cross-conjugated dienones with pendent azide side chains undergo interrupted Nazarov trapping, leading to peroxy-bridged indolizidinones in good yields. This process is proposed to involve skeletal rearrangement of the initial trapping product, with loss of dinitrogen, to give an intermediate 1,4-betaine, which then undergoes reaction with atmospheric oxygen. The endoperoxide products can be reduced under catalytic hydrogenation conditions to furnish alpha-hydroxylactams.

  DOI：

  10.1021/ol070053m
• 作为产物：
  描述：

  ((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 叔丁基锂 、 碳酸氢钠 、 potassium carbonate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 30.0h， 生成 5-Azido-1-(cyclohexen-1-yl)-2-methylidenepentan-1-one
  参考文献：
  名称：

  Intramolecular Azide Trapping of the Nazarov Intermediate:  Formation of Peroxy-Bridged Indolizidinones via a Deep-Seated Rearrangement and Aerobic Oxidation

  摘要：

  Cross-conjugated dienones with pendent azide side chains undergo interrupted Nazarov trapping, leading to peroxy-bridged indolizidinones in good yields. This process is proposed to involve skeletal rearrangement of the initial trapping product, with loss of dinitrogen, to give an intermediate 1,4-betaine, which then undergoes reaction with atmospheric oxygen. The endoperoxide products can be reduced under catalytic hydrogenation conditions to furnish alpha-hydroxylactams.

  DOI：

  10.1021/ol070053m

文献信息

• Intramolecular Azide Trapping of the Nazarov Intermediate:  Formation of Peroxy-Bridged Indolizidinones via a Deep-Seated Rearrangement and Aerobic Oxidation
  作者：Ali Rostami、Yong Wang、Atta M. Arif、Robert McDonald、F. G. West

  DOI：10.1021/ol070053m

  日期：2007.2.1

  Cross-conjugated dienones with pendent azide side chains undergo interrupted Nazarov trapping, leading to peroxy-bridged indolizidinones in good yields. This process is proposed to involve skeletal rearrangement of the initial trapping product, with loss of dinitrogen, to give an intermediate 1,4-betaine, which then undergoes reaction with atmospheric oxygen. The endoperoxide products can be reduced under catalytic hydrogenation conditions to furnish alpha-hydroxylactams.