(Z)-1-phenyl-2-tert-butoxy-3--5-hexen-1-one | 145278-43-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-phenyl-2-tert-butoxy-3--5-hexen-1-one
• 英文别名: (3Z)-3-[iodo(trimethylsilyl)methylidene]-2-[(2-methylpropan-2-yl)oxy]-1-phenylhex-5-en-1-one
• CAS: 145278-43-9
• 化学式: C₂₀H₂₉IO₂Si
• 分子量: 456.439
• InChiKey: YIEQPWACDXOUHQ-KNTRCKAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  叔丁基炔丙基乙醚 在 正丁基锂 作用下， 反应 0.67h， 生成 (Z)-1-phenyl-2-tert-butoxy-3--5-hexen-1-one
  参考文献：
  名称：

  Reactivity of allylic dimetallic zinc reagents. 1

  摘要：

  Allylic 1,1-dimetallic species 2, prepared in situ from the propargylic ether 1, are multicoupling reagents. They were allowed to react in a one-pot maction, with a large variety of electrophiles E1-carbonyl compounds (acyl chlorides, aldehydes, ketones, phenyl isocyanate, methyl chloroformate), alkyl bromides, and an amino ether-and then E2-acidic water, iodine, aryl or vinyl iodide in the presence of palladium(0). The isolated yields, based on 1 (5 steps), are fair to good in most cases. The first attack (E1) always occurs on the carbon atom alpha to the oxygen; the second attack (E2) is regio- and stereoselective on the carbon atom a to the TMS moiety.

  DOI：

  10.1021/jo00051a042