2-methyl-2-(5-oxo-2,5-dihydrofuran-2-yl)chroman-4-one | 1393689-24-1

• 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-methyl-2-(5-oxo-2,5-dihydrofuran-2-yl)chroman-4-one
• 英文别名: 2-methyl-2-(5-oxo-2H-furan-2-yl)-3H-chromen-4-one
• CAS: 1393689-24-1
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: CJGDTPKEAXEBQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙酰基-2'-羟基苯乙酮 在 盐酸 、 三甲基氯硅烷 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 2-methyl-2-(5-oxo-2,5-dihydrofuran-2-yl)chroman-4-one
  参考文献：
  名称：

  TMSI-Promoted Vinylogous Michael Addition of Siloxyfuran to 2-Substituted Chromones: A General Approach for the Total Synthesis of Chromanone Lactone Natural Products

  摘要：

  A concise and facile synthetic protocol for the construction of the 2-gamma-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (+/-)-microdiplodiasone, (+/-)-lachnone C, and (+/-)-gonytolides C and G.

  DOI：

  10.1021/jo502571r

文献信息

• Access to 2-alkyl chromanones via a conjugate addition approach
  作者：Louise A. Stubbing、Freda F. Li、Daniel P. Furkert、Vittorio E. Caprio、Margaret A. Brimble

  DOI：10.1016/j.tet.2012.05.115

  日期：2012.8

  The introduction of alkyl substituents at C-2 of chromanones via conjugate addition of silyl enol ethers to a variety of chromenones is reported. In most cases racemic 2-alkyl chromanones were obtained in good yield in the presence of TMSOTf. The copper(II)-promoted conjugate addition of silyl enol ethers to chromenones was also carried out, albeit in low yields and no selectivity. Reliable syntheses of the chromenones via acylation of the corresponding beta-diketo-compounds are also described. (C) 2012 Elsevier Ltd. All rights reserved.
• TMSI-Promoted Vinylogous Michael Addition of Siloxyfuran to 2-Substituted Chromones: A General Approach for the Total Synthesis of Chromanone Lactone Natural Products
  作者：Jie Liu、Zhanchao Li、Pei Tong、Zhixiang Xie、Yuan Zhang、Ying Li

  DOI：10.1021/jo502571r

  日期：2015.2.6

  A concise and facile synthetic protocol for the construction of the 2-gamma-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (+/-)-microdiplodiasone, (+/-)-lachnone C, and (+/-)-gonytolides C and G.