2,2-dimethyl-6-vinyl-2H-chromen-5-ol | 1252582-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2-dimethyl-6-vinyl-2H-chromen-5-ol
• 英文别名: 6-Ethenyl-2,2-dimethylchromen-5-ol
• CAS: 1252582-83-4
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: IVWNMEHTBBDGDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2,2-dimethyl-6-vinyl-2H-chromen-5-ol 在 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 copper(II) acetate monohydrate 、 silver carbonate 作用下， 以 邻二甲苯 为溶剂， 反应 10.0h， 以48%的产率得到邪蒿素
  参考文献：
  名称：

  Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives

  摘要：

  Cp*Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.

  DOI：

  10.1021/acs.orglett.5b02728
• 作为产物：
  描述：

  5-羟基-2,2-二甲基-2H-色烯-6-甲醛 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97%的产率得到2,2-dimethyl-6-vinyl-2H-chromen-5-ol
  参考文献：
  名称：

  德桂林、Tephrosin 的简明模块化不对称合成及其作用机制研究

  摘要：

  德桂林和替弗罗辛合成的简明性质和模块性（所描述的逆合成分析）应有助于获得标记的类似物，以剖析这一重要药效团的作用机制。

  DOI：

  10.1002/chem.201001080

文献信息

• Concise Modular Asymmetric Synthesis of Deguelin, Tephrosin and Investigation into Their Mode of Action
  作者：José Garcia、Sofia Barluenga、Kristin Beebe、Len Neckers、Nicolas Winssinger

  DOI：10.1002/chem.201001080

  日期：2010.8.23

  The concise nature and modularity of the synthesis described for deguelin and tephrosin (retrosynthetic analysis depicted) should facilitate access to labeled analogues to dissect the mechanism of action of this important pharmacophore.

  德桂林和替弗罗辛合成的简明性质和模块性（所描述的逆合成分析）应有助于获得标记的类似物，以剖析这一重要药效团的作用机制。
• Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives
  作者：Xu-Ge Liu、Shang-Shi Zhang、Chun-Yong Jiang、Jia-Qiang Wu、Qingjiang Li、Honggen Wang

  DOI：10.1021/acs.orglett.5b02728

  日期：2015.11.6

  Cp*Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.