4-butyl-2,2-dimethyl-1,3-dioxan-5-one | 379717-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-butyl-2,2-dimethyl-1,3-dioxan-5-one
• CAS: 379717-22-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: QFGURDPCRYYSEB-UHFFFAOYSA-N

物化性质

• 沸点：
  254.5±30.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-butyl-2,2-dimethyl-1,3-dioxan-5-one 在 sodium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (Z)-2-triethylsilyloxyhept-2-enal
  参考文献：
  名称：

  Stereoselective Preparation of (Z)-2-(Trialkylsilyloxy)-2-alkenals by Retrocycloaddition Reactions of 4H-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful Reactants for Lewis Acid Catalyzed [4 + 3] Cyclizations

  摘要：

  [GRAPHICS]Retrocycloadditions of 4H-4-alkyl-5-(trialylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereos electivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.

  DOI：

  10.1021/ol016668f
• 作为产物：
  描述：

  2,2-二甲基-1,3-二恶烷-5-酮 在 正丁基锂 、 4 A molecular sieve 、 二乙胺 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 4.0h， 生成 4-butyl-2,2-dimethyl-1,3-dioxan-5-one
  参考文献：
  名称：

  Stereoselective Preparation of (Z)-2-(Trialkylsilyloxy)-2-alkenals by Retrocycloaddition Reactions of 4H-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful Reactants for Lewis Acid Catalyzed [4 + 3] Cyclizations

  摘要：

  [GRAPHICS]Retrocycloadditions of 4H-4-alkyl-5-(trialylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereos electivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.

  DOI：

  10.1021/ol016668f

文献信息

• A gold-catalyzed [4+3]-cycloaddition of functionalized dioxines
  作者：Michael Harmata、Chaofeng Huang

  DOI：10.1016/j.tetlet.2009.07.111

  日期：2009.10

  Treatment of 5-silyloxydioxins with 5 mol % AuCl3/AgSbF6 in the presence of cyclopentadiene or furan results in the rapid formation of [4+3]-cycloadducts at room temperature.

  在环戊二烯或呋喃存在下，用5 mol％AuCl 3 / AgSbF 6处理5-甲硅烷氧基二恶英导致在室温下快速形成[4 + 3]-环加合物。
• Asymmetric Synthesis of Monoprotected Double Allylic Alcohols
  作者：Dieter Enders、Matthias Voith

  DOI：10.1055/s-2002-33341

  日期：——

  The enantioselective synthesis of mono-TBS protected, double allylic alcohols 5 (ee = 90-94%) employing the SAMP/RAMP-hydrazone methodology is reported. Acetonide protected, α-substituted ketodiols 2 were synthesized from SAMP-hydrazone 1 which were converted to exocyclic olefins 3 by a racemization-free Wittig reaction. Acidic acetal cleavage to 4 followed by selective TBS protection furnished title compounds 5 in very good overall yields and enantiomeric excesses.

  报告采用 SAMP/RAMP- 酰腙方法，对映选择性地合成了单-TBS 保护的双烯丙醇 5（ee = 90-94%）。 由 SAMP 酰腙 1 合成了受乙酮保护的δ-取代酮二醇 2，并通过无外消旋化的 Wittig 反应将其转化为外环烯烃 3。 酸性乙缩醛裂解成 4，然后选择性 TBS 保护，得到了标题化合物 5，总产率和对映体过量率都非常高。
• Stereoselective Preparation of (<i>Z</i>)-2-(Trialkylsilyloxy)-2-alkenals by Retrocycloaddition Reactions of 4<i>H</i>-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful Reactants for Lewis Acid Catalyzed [4 + 3] Cyclizations
  作者：Ronald A. Aungst、Raymond L. Funk

  DOI：10.1021/ol016668f

  日期：2001.11.1

  [GRAPHICS]Retrocycloadditions of 4H-4-alkyl-5-(trialylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereos electivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.