ethyl 4,4-dimethyl-6-oxocyclohex-1-enecarboxylate | 1425313-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,4-dimethyl-6-oxocyclohex-1-enecarboxylate
• 英文别名: Ethyl 4,4-dimethyl-6-oxocyclohexene-1-carboxylate；ethyl 4,4-dimethyl-6-oxocyclohexene-1-carboxylate
• CAS: 1425313-23-0
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: JGZACHBYCUIYTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4,4-dimethyl-6-oxocyclohex-1-enecarboxylate 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 、 S-4,5-二氢-2-(2-((S)-4,5-二氢-4-异丙基噁唑-2-基)丙-2-基)-4-异丙基噁唑 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-ethyl 2-((diphenoxyphosphoryl)oxy)-4,4-dimethyl-6-((R)-5-oxo-2,5-dihydrofuran-2-yl)cyclohex-1-enecarboxylate
  参考文献：
  名称：

  Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters

  摘要：

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.

  DOI：

  10.1021/jo3020648

文献信息

• Asymmetric Catalytic Conjugate Addition of Cyanide to Chromones and β-Substituted Cyclohexenones
  作者：Yuhao Mo、Qiyou Chen、Jinzhao Li、Dong Ye、Yuqiao Zhou、Shunxi Dong、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acscatal.2c05509

  日期：2023.1.20

  combination with chiral N,N′-dioxides facilitated the reaction well, revealing a close connection between the outcome of the reaction and the Lewis acidity with metal ion radii. The application of the methods was highlighted by the facile synthesis of the bioactive compounds repinotan and sarizotan.

  通过手性路易斯酸和非手性有机碱的双重催化，实现了环状 α,β-不饱和酮的高度对映选择性共轭氰化。多种色酮和β-取代的环己烯酮在温和条件下以高对映选择性高收率转化为所需的β-氰基酮衍生物。金属盐 Ce(OTf) 3和 Ba(OTf) 2与手性N , N '-二氧化物的结合很好地促进了反应，揭示了反应结果与路易斯酸度与金属离子半径之间的密切联系。生物活性化合物 repinotan 和 sarizotan 的轻松合成突出了这些方法的应用。
• Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters
  作者：Xavier Jusseau、Pascal Retailleau、Laurent Chabaud、Catherine Guillou

  DOI：10.1021/jo3020648

  日期：2013.3.15

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.