4-methoxy-1-propyl-2,2a,3,4-tetrahydro-cyclobuta[a]naphthalene | 844638-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methoxy-1-propyl-2,2a,3,4-tetrahydro-cyclobuta[a]naphthalene
• 英文别名: 4-Methoxy-1-propyl-2,2a,3,4-tetrahydrocyclobuta[a]naphthalene
• CAS: 844638-81-9
• 化学式: C₁₆H₂₀O
• 分子量: 228.334
• InChiKey: YNBCRIMEMVSGFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methoxy-1-propyl-2,2a,3,4-tetrahydro-cyclobuta[a]naphthalene 以 乙腈 为溶剂， 反应 14.0h， 以56%的产率得到1-methoxy-4-(1-methylidenebutyl)-1,2-dihydronaphthalene
  参考文献：
  名称：

  PtBr₂-Catalyzed Consecutive Enyne Metathesis−Aromatization of 1-(1-Methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:  Dual Role of the Pt Catalyst

  摘要：

  1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the eryne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.

  DOI：

  10.1021/jo048273q
• 作为产物：
  描述：

  1-(1-methoxybut-3-enyl)-2-(pent-1-ynyl)benzene 在 platinum(II) bromde 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以60%的产率得到4-methoxy-1-propyl-2,2a,3,4-tetrahydro-cyclobuta[a]naphthalene
  参考文献：
  名称：

  PtBr₂-Catalyzed Consecutive Enyne Metathesis−Aromatization of 1-(1-Methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:  Dual Role of the Pt Catalyst

  摘要：

  1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the eryne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.

  DOI：

  10.1021/jo048273q