tert-butyl 2,6,6-trimethyl-4-thioxo-5,6-dihydro-4H-pyran-3-carboxylate | 245069-20-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: tert-butyl 2,6,6-trimethyl-4-thioxo-5,6-dihydro-4H-pyran-3-carboxylate
• 英文别名: tert-butyl 2,2,6-trimethyl-4-sulfanylidene-3H-pyran-5-carboxylate
• CAS: 245069-20-9
• 化学式: C₁₃H₂₀O₃S
• 分子量: 256.366
• InChiKey: MUYHRQCAAVKICZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2,6,6-trimethyl-4-thioxo-5,6-dihydro-4H-pyran-3-carboxylate 、 alkaline earth salt of/the/ methylsulfuric acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Tert-butyl 4-[(4-methoxyphenyl)methylsulfanyl]-2,6,6-trimethylpyran-3-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
• 作为产物：
  描述：

  t-bytil 3,4-dihydro-2,2,6-trimethyl-4-oxo-2H-pyran-5-carboxylate 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以66%的产率得到tert-butyl 2,6,6-trimethyl-4-thioxo-5,6-dihydro-4H-pyran-3-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