3-(cyclohexylethynyl)-5,5-dimethylcyclohex-2-en-1-one | 1312797-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(cyclohexylethynyl)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 1312797-50-4
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: WKVABVBZRNWUJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(cyclohexylethynyl)-5,5-dimethylcyclohex-2-en-1-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以44%的产率得到3-(5-cyclohexyl-2H-triazol-4-yl)-5,5-dimethylcyclohex-2-en-1-one
  参考文献：
  名称：

  Design, Synthesis, and Diversification of 3,5-Substituted Enone Library

  摘要：

  This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloacklition sequence. The library was analyzed by principal component analysis to examine its diversity.

  DOI：

  10.1021/co200070m
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 3-(cyclohexylethynyl)-5,5-dimethylcyclohex-2-en-1-one
  参考文献：
  名称：

  Design, Synthesis, and Diversification of 3,5-Substituted Enone Library

  摘要：

  This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloacklition sequence. The library was analyzed by principal component analysis to examine its diversity.

  DOI：

  10.1021/co200070m

文献信息

• Synthesis of β-Substituted Cyclic Enones via Phosphonium Salt-Activated, Palladium-Catalyzed Cross-Coupling of Cyclic 1,3-Diones
  作者：Shyh-Ming Yang、Gee-Hong Kuo、Michael D. Gaul、William V. Murray

  DOI：10.1021/acs.joc.6b00317

  日期：2016.4.15

  salt-activated, Pd-catalyzed Suzuki–Miyaura and Sonogashira cross-coupling reactions of cyclic 1,3-diones in the synthesis of β-substituted cyclic enones are described. These transformations exhibit good isolated yield and high generality with respect to both substrates and coupling partners. Extension of the substrate scope to cyclic 1,3-dione equivalents, such as 2-cyanocyclohexanone (4), is also briefly examined

  描述了在合成β-取代的环状烯酮时，环状1,3-二酮的salt盐活化，Pd催化的Suzuki-Miyaura和Sonogashira交叉偶联反应。这些转化相对于底物和偶联伴侣表现出良好的分离产率和高通用性。还简要地研究了将底物范围扩展至环状1，3-二酮等同物，例如2-氰基环己酮（4）。