(E)-2-(3'-methyloct-2'-en-6'-ynyl)-4-benzyloxyphenol | 1163722-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-(3'-methyloct-2'-en-6'-ynyl)-4-benzyloxyphenol
• 英文别名: 2-[(E)-3-methyloct-2-en-6-ynyl]-4-phenylmethoxyphenol
• CAS: 1163722-37-9
• 化学式: C₂₂H₂₄O₂
• 分子量: 320.431
• InChiKey: VHFDVBURYYLZPV-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(3'-methyloct-2'-en-6'-ynyl)-4-benzyloxyphenol 在 PPh₃AuNTf₂ 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以95%的产率得到rac-(4aS,9aS)-7-(benzyloxy)-1,4a-dimethyl-4,4a,9,9a-tetrahydro-3H-xanthene
  参考文献：
  名称：

  Mimicking Polyolefin Carbocyclization Reactions: Gold-Catalyzed Intramolecular Phenoxycyclization of 1,5-Enynes

  摘要：

  PPh3AuNTf2 promotes highly efficient intramolecular phenoxycyclization reactions on 1,5-enynes under mild conditions. The original tricyclic and functionalized heterocycles were isolated in good to excellent yields. The 6-endo cyclization process is predominant and operates via a biomimetic cascade cation-olefin process. The efficiency of this system was further demonstrated in the cycloisomerization reaction of a 1,5,9-dienyne.

  DOI：

  10.1021/ol900864n
• 作为产物：
  描述：

  4-苄氧基苯酚 、 (E)-1-bromo-3-methyloct-2-en-6-yne 在 sodium hydride 作用下， 以 甲苯 为溶剂， 生成 (E)-2-(3'-methyloct-2'-en-6'-ynyl)-4-benzyloxyphenol
  参考文献：
  名称：

  Mimicking Polyolefin Carbocyclization Reactions: Gold-Catalyzed Intramolecular Phenoxycyclization of 1,5-Enynes

  摘要：

  PPh3AuNTf2 promotes highly efficient intramolecular phenoxycyclization reactions on 1,5-enynes under mild conditions. The original tricyclic and functionalized heterocycles were isolated in good to excellent yields. The 6-endo cyclization process is predominant and operates via a biomimetic cascade cation-olefin process. The efficiency of this system was further demonstrated in the cycloisomerization reaction of a 1,5,9-dienyne.

  DOI：

  10.1021/ol900864n

文献信息

• Mimicking Polyolefin Carbocyclization Reactions: Gold-Catalyzed Intramolecular Phenoxycyclization of 1,5-Enynes
  作者：Patrick Yves Toullec、Thomas Blarre、Véronique Michelet

  DOI：10.1021/ol900864n

  日期：2009.7.2

  PPh3AuNTf2 promotes highly efficient intramolecular phenoxycyclization reactions on 1,5-enynes under mild conditions. The original tricyclic and functionalized heterocycles were isolated in good to excellent yields. The 6-endo cyclization process is predominant and operates via a biomimetic cascade cation-olefin process. The efficiency of this system was further demonstrated in the cycloisomerization reaction of a 1,5,9-dienyne.