methyl 4-ethoxycarbonyl-4-methyl-5-oxohexanonate | 913346-53-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4-ethoxycarbonyl-4-methyl-5-oxohexanonate
• 英文别名: 2-Acetyl-2-methylpentanedioic acid, 1-ethyl ester 5-methyl ester；1-O-ethyl 5-O-methyl 2-acetyl-2-methylpentanedioate
• CAS: 913346-53-9
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: FAOLYWCHYSJDOY-UHFFFAOYSA-N

物化性质

• 沸点：
  294.3±20.0 °C(predicted)
• 密度：
  1.074±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-ethoxycarbonyl-4-methyl-5-oxohexanonate 在 盐酸 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以550 mg的产率得到4-methyl-5-oxohexanoic acid
  参考文献：
  名称：

  Direct Enantioselective Brønsted Acid Catalyzed N-Acyliminium Cyclization Cascades of Tryptamines and Ketoacids

  摘要：

  A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with gamma- and delta-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).

  DOI：

  10.1021/ol101651t
• 作为产物：
  描述：

  2-甲基乙酰乙酸乙酯 、 丙烯酸甲酯（MA） 在 4-(didecylamino)pyridine 作用下， 以 水 为溶剂， 反应 7.5h， 以88%的产率得到methyl 4-ethoxycarbonyl-4-methyl-5-oxohexanonate
  参考文献：
  名称：

  开发新的DMAP相关的有机催化剂，用于水中的β-酮酸酯的迈克尔加成反应

  摘要：

  已经开发出一种在纯水中进行β-酮酸酯的迈克尔加成反应的通用有效方案。通过新设计的DMAP相关有机催化剂（例如4-（十二烷基氨基）吡啶）成功催化了反应，并以高收率或高收率获得了所需的迈克尔加合物

  DOI：

  10.1016/j.tetlet.2009.04.025

文献信息

• Development of new DMAP-related organocatalysts for use in the Michael addition reaction of β-ketoesters in water
  作者：Kyungmin Ko、Keiji Nakano、Shigeru Watanabe、Yoshiyasu Ichikawa、Hiyoshizo Kotsuki

  DOI：10.1016/j.tetlet.2009.04.025

  日期：2009.7

  A general and efficient protocol for the Michael addition reactions of β-ketoesters in pure water has been developed. The reactions are successfully catalyzed by newly designed DMAP-related organocatalysts such as 4-(didecylamino)pyridine, and the desired Michael adducts are obtained in good to high yields

  已经开发出一种在纯水中进行β-酮酸酯的迈克尔加成反应的通用有效方案。通过新设计的DMAP相关有机催化剂（例如4-（十二烷基氨基）吡啶）成功催化了反应，并以高收率或高收率获得了所需的迈克尔加合物
• Efficient Organocatalytic Michael Addition Reaction of β−Ketoesters under High Pressure
  作者：Hiyoshizo Kotsuki、Maya Moritaka、Keiji Nakano

  DOI：10.3987/com-13-12818

  日期：——

  The Michael addition reaction of beta-ketoesters was efficiently promoted by a cooperative dual catalyst system composed by DMAP and thiourea A under high-pressure conditions (0.8 GPa) in toluene. The expected relatively congested adducts of 1,5-dicarbonyl compounds were prepared in high to excellent yield.
• Direct Enantioselective Brønsted Acid Catalyzed <i>N</i>-Acyliminium Cyclization Cascades of Tryptamines and Ketoacids
  作者：Chloe A. Holloway、Michael E. Muratore、R. lan Storer、Darren J. Dixon

  DOI：10.1021/ol101651t

  日期：2010.11.5

  A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with gamma- and delta-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).