(E)-2-(2-(1,3-dithiolan-2-ylidene)-6,6-dimethyl-3-oxohept-4-enyl)-5,5-dimethylcyclohexane-1,3-dione | 1142319-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-(2-(1,3-dithiolan-2-ylidene)-6,6-dimethyl-3-oxohept-4-enyl)-5,5-dimethylcyclohexane-1,3-dione
• 英文别名: 2-[(E)-2-(1,3-dithiolan-2-ylidene)-6,6-dimethyl-3-oxohept-4-enyl]-5,5-dimethylcyclohexane-1,3-dione
• CAS: 1142319-88-7
• 化学式: C₂₀H₂₈O₃S₂
• 分子量: 380.573
• InChiKey: HKCGASJQBJQEOQ-VOTSOKGWSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  520.4±50.0 °C(predicted)
• 密度：
  1.141±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (E)-1-(1,3-dithiolan-2-ylidene)-5,5-dimethylhex-3-en-2-one 、 5,5-二甲基-1,3-环己二酮 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以66%的产率得到(E)-2-(2-(1,3-dithiolan-2-ylidene)-6,6-dimethyl-3-oxohept-4-enyl)-5,5-dimethylcyclohexane-1,3-dione
  参考文献：
  名称：

  α-Alkenoyl Ketene S,S-Acetal-Based Multicomponent Reaction: An Efficient Approach for the Selective Construction of Polyfunctionalized Cyclohexanones

  摘要：

  A versatile multicomponent reaction based on the new four-carbon synthons alpha-alkenoyl ketene S,S-acetals 1 has been developed. This three-component reaction of readily available alpha-alkenoyl ketene S,S-acetals 1 with aldehydes 2 and active methylene compounds 3 proceeds smoothly in acidic medium (glacial acetic acid in tetrahydrofuran) to give various polyfunctionalized cyclohexanones 4, 5, and 6 in a highly regio- and diastereoselective manner with good to excellent yields. The reaction can tolerate a broad range of substituents in the three components involved and is proposed to proceed via a tandem Knoevenagel-intermolecular Michael-intramolecular Michael sequence. As an extension of the synthetic application of polyfunctionalized cyclohexanones obtained, unsymmetrical biaryls 7 were synthesized in almost quantitative yields by simple transformations of the corresponding cycloadducts 6.

  DOI：

  10.1021/jo900217g

文献信息

• α-Alkenoyl Ketene <i>S</i>,<i>S</i>-Acetal-Based Multicomponent Reaction: An Efficient Approach for the Selective Construction of Polyfunctionalized Cyclohexanones
  作者：Yuhui Ma、Mang Wang、Dan Li、Bahargul Bekturhun、Jun Liu、Qun Liu

  DOI：10.1021/jo900217g

  日期：2009.4.17

  A versatile multicomponent reaction based on the new four-carbon synthons alpha-alkenoyl ketene S,S-acetals 1 has been developed. This three-component reaction of readily available alpha-alkenoyl ketene S,S-acetals 1 with aldehydes 2 and active methylene compounds 3 proceeds smoothly in acidic medium (glacial acetic acid in tetrahydrofuran) to give various polyfunctionalized cyclohexanones 4, 5, and 6 in a highly regio- and diastereoselective manner with good to excellent yields. The reaction can tolerate a broad range of substituents in the three components involved and is proposed to proceed via a tandem Knoevenagel-intermolecular Michael-intramolecular Michael sequence. As an extension of the synthetic application of polyfunctionalized cyclohexanones obtained, unsymmetrical biaryls 7 were synthesized in almost quantitative yields by simple transformations of the corresponding cycloadducts 6.