6-tert-Butyl-2,3-dihydro-2,2-dimethyl-4H-pyran-4-one | 55473-49-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-tert-Butyl-2,3-dihydro-2,2-dimethyl-4H-pyran-4-one
• 英文别名: Dimethyl-2,2-t-butyl-6-dihydro-2,3-pyron-4；6-tert-butyl-2,2-dimethyl-2,3-dihydro-pyran-4-one；6-tert-butyl-2,2-dimethyl-3H-pyran-4-one
• CAS: 55473-49-9
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: XHKJGSWARUEEEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-tert-Butyl-2,3-dihydro-2,2-dimethyl-4H-pyran-4-one 在 劳森试剂 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 6-Tert-butyl-4-[(4-methoxyphenyl)methylsulfanyl]-2,2-dimethylpyran
  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：

  N-甲氧基-N,2,2-三甲基丙酰胺 在 氢溴酸 、 异丙基氯化镁 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成 6-tert-Butyl-2,3-dihydro-2,2-dimethyl-4H-pyran-4-one
  参考文献：
  名称：

  2,2-二烷基-2,3-二氢-4 H-吡喃-4-酮的新的一般合成及其在羰基-炔烃与乙炔交换反应中原位制备富电子二烯的应用†

  摘要：

  II和III型取代的2,2-二烷基-2,3-二氢-4 H-吡喃-4-酮是通过酸催化环化相应的取代炔基酮I制备的，收率良好至优异（方案1）。这些2,2-二烷基-2,3-二氢-4 H-吡喃-4-酮II和III已用于在羰基炔烃交换中原位制备IV - VI型高反应性二烯（方案2）与贫电子炔烃VII反应生成高度取代的芳族化合物VIII和IX。这些反应以良好的收率和优异的区域选择性进行。芳基取代的2，2-二烷基-2，3-二氢-4 H-吡喃-4-酮III（R 1＝ Ar）随后产生高度取代的联芳基。提出了形成2，2-二烷基-2，3-二氢-4 H-吡喃-4-酮以及与贫电子乙炔的羰基炔交换反应的反应机理。

  DOI：

  10.1002/hlca.19910740106

文献信息

• CATHEPSIN S INHIBITORS
  申请人：Lin Chun-Cheng

  公开号：US20110166141A1

  公开（公告）日：2011-07-07

  Cathepsin S inhibitors having formula (I), (II), (III) or (IV) as shown in the specification. These inhibitors can be used to treat cancer and autoimmune/inflammatory diseases.

  具有(I)、(II)、(III)或(IV)公式的卡特普西林S抑制剂，如规范所示。这些抑制剂可用于治疗癌症和自身免疫/炎症性疾病。
• US8895497B2
  申请人：——

  公开号：US8895497B2

  公开（公告）日：2014-11-25
• A New General Synthesis of 2,2-Dialkyl-2,3-dihydro-4H-pyran-4-ones and Their Application for thein situ Preparation of Electron-Rich Dienes in Carbonyl-Alkyne Exchange Reactions with Acetylenes
  作者：Daniel Obrecht

  DOI：10.1002/hlca.19910740106

  日期：1991.1.30

  reactions with electron-poor alkynes VII to yield the highly substituted aromatic compounds VIII and IX. These reactions proceed in good yields and with excellent degree of regioselectivity. Aryl-substituted 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones III (R1 = Ar) subsequently yield highly substituted biaryls. Reaction mechanisms are presented for the formation of the 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones

  II和III型取代的2,2-二烷基-2,3-二氢-4 H-吡喃-4-酮是通过酸催化环化相应的取代炔基酮I制备的，收率良好至优异（方案1）。这些2,2-二烷基-2,3-二氢-4 H-吡喃-4-酮II和III已用于在羰基炔烃交换中原位制备IV - VI型高反应性二烯（方案2）与贫电子炔烃VII反应生成高度取代的芳族化合物VIII和IX。这些反应以良好的收率和优异的区域选择性进行。芳基取代的2，2-二烷基-2，3-二氢-4 H-吡喃-4-酮III（R 1＝ Ar）随后产生高度取代的联芳基。提出了形成2，2-二烷基-2，3-二氢-4 H-吡喃-4-酮以及与贫电子乙炔的羰基炔交换反应的反应机理。
• 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.