acetic acid 1-[1-(3-hydroxy-propyl)-vinyl]-2-methyl-3-phenyl-allyl ester | 929295-91-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: acetic acid 1-[1-(3-hydroxy-propyl)-vinyl]-2-methyl-3-phenyl-allyl ester
• CAS: 929295-91-0
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: LWLVGACFSLDJRK-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  acetic acid 1-[1-(3-hydroxy-propyl)-vinyl]-2-methyl-3-phenyl-allyl ester 在 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以85%的产率得到[(E)-7-azido-2-methyl-4-methylidene-1-phenylhept-1-en-3-yl] acetate
  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 、 叔丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 正戊烷 为溶剂， 反应 19.5h， 生成 acetic acid 1-[1-(3-hydroxy-propyl)-vinyl]-2-methyl-3-phenyl-allyl ester
  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