methyl 3-bromo-5-(hexylsulfanyl)biphenyl-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-bromo-5-(hexylsulfanyl)biphenyl-2-carboxylate
• 英文别名: Methyl 2-bromo-4-hexylsulfanyl-6-phenylbenzoate
• 化学式: C₂₀H₂₃BrO₂S
• 分子量: 407.371
• InChiKey: FUYVDKJCYXDFND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴炔丙酸甲酯 、 4-Hexylsulfanyl-2,2-dimethyl-6-phenylpyran 在 氯化二乙基铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 methyl 3-bromo-5-(hexylsulfanyl)biphenyl-2-carboxylate
  参考文献：
  名称：

  Regioselective Synthesis of Highly Substituted Aromatic Sulfides via Carbonyl−Alkyne Exchange Reaction

  摘要：

  Carbonyl-alkyne exchange reaction of 2,2-dimethyldihydropyran-4-thione-derived dienes with acetylenic ketones leads to highly substituted aromatic sulfides. The reaction proceeds with a high degree of regioselectivity and in good yields. Addition of Et2AlCl considerably increases the scope of usable acetylenic ketones. The starting materials, dihydropyran-4-one and alpha-alkynyl ketone derivatives, are readily available reactive building blocks. Additional diversity can be introduced through straightforward derivatization reactions at the sulfur atom. The use of solid-supported reagents and trapping agents allows the reaction to be carried out in a parallel format which might render such a concept attractive for the synthesis of compound libraries.

  DOI：

  10.1021/jo990110s

文献信息

• Regioselective Synthesis of Highly Substituted Aromatic Sulfides via Carbonyl−Alkyne Exchange Reaction
  作者：Daniel Obrecht、Cornelia Zumbrunn、Klaus Müller

  DOI：10.1021/jo990110s

  日期：1999.8.1

  Carbonyl-alkyne exchange reaction of 2,2-dimethyldihydropyran-4-thione-derived dienes with acetylenic ketones leads to highly substituted aromatic sulfides. The reaction proceeds with a high degree of regioselectivity and in good yields. Addition of Et2AlCl considerably increases the scope of usable acetylenic ketones. The starting materials, dihydropyran-4-one and alpha-alkynyl ketone derivatives, are readily available reactive building blocks. Additional diversity can be introduced through straightforward derivatization reactions at the sulfur atom. The use of solid-supported reagents and trapping agents allows the reaction to be carried out in a parallel format which might render such a concept attractive for the synthesis of compound libraries.