4-[(4-Methoxyphenyl)methylsulfanyl]-2,2,5,6-tetramethylpyran | 1026531-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[(4-Methoxyphenyl)methylsulfanyl]-2,2,5,6-tetramethylpyran
• CAS: 1026531-71-4
• 化学式: C₁₇H₂₂O₂S
• 分子量: 290.426
• InChiKey: MEHGVTGVGCAKQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-oxo-4-phenylbut-2-ynoate 、 4-[(4-Methoxyphenyl)methylsulfanyl]-2,2,5,6-tetramethylpyran 以 甲苯 为溶剂， 反应 24.0h， 生成 methyl 2-benzoyl-5-(4-methoxybenzylsulfanyl)-3,4-dimethylbenzoate
  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
• 作为产物：
  描述：

  2,3,6,6-tetramethyl-5,6-dihydro-4H-pyran-4-one 在 劳森试剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 4-[(4-Methoxyphenyl)methylsulfanyl]-2,2,5,6-tetramethylpyran
  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.