3-methoxy-4-(pent-3-ynyl)phenol | 1184937-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-methoxy-4-(pent-3-ynyl)phenol
• 英文别名: 3-methoxy-4-pent-3-ynylphenol
• CAS: 1184937-38-9
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: VKOBOOSXMUNDKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-methoxy-4-(pent-3-ynyl)phenol 在 碳酸氢钠 、 [双(三氟乙酰氧基)碘]苯 作用下， 反应 0.17h， 以42%的产率得到3,4-dimethoxy-4-(pent-3-ynyl)cyclohexa-2,5-dienone
  参考文献：
  名称：

  Palladium-Catalyzed Reactions of Cyclohexadienones: Regioselective Cyclizations Triggered by Alkyne Acetoxylation

  摘要：

  Regioselective cyclizations of alkyne-tethered cyclohexadienones can be accomplished under palladium catalysis. The cyclization involves an Initial Pd-mediated acetoxylation of the alkyne, followed by migratory insertion and protonolysis of the resulting palladium enolate. The predictable regloselectivity of these atom-economical and stereoselective reactions is influenced by developing steric interactions during migratory insertion of a vinyl palladium intermediate.

  DOI：

  10.1021/ol901642w
• 作为产物：
  描述：

  tert-butyl(3-methoxy-4-(pent-3-ynyl)phenoxy)dimethylsilane 在 lithium hydroxide monohydrate 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以99%的产率得到3-methoxy-4-(pent-3-ynyl)phenol
  参考文献：
  名称：

  Palladium-Catalyzed Reactions of Cyclohexadienones: Regioselective Cyclizations Triggered by Alkyne Acetoxylation

  摘要：

  Regioselective cyclizations of alkyne-tethered cyclohexadienones can be accomplished under palladium catalysis. The cyclization involves an Initial Pd-mediated acetoxylation of the alkyne, followed by migratory insertion and protonolysis of the resulting palladium enolate. The predictable regloselectivity of these atom-economical and stereoselective reactions is influenced by developing steric interactions during migratory insertion of a vinyl palladium intermediate.

  DOI：

  10.1021/ol901642w