ethyl 6-methoxy-7-methyl-2H-1-benzopyran-4-one-2-carboxylate | 630390-77-1

• 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: ethyl 6-methoxy-7-methyl-2H-1-benzopyran-4-one-2-carboxylate
• 英文别名: Ethyl 6-methoxy-7-methyl-4-oxo-2,3-dihydrochromene-2-carboxylate；ethyl 6-methoxy-7-methyl-4-oxo-2,3-dihydrochromene-2-carboxylate
• CAS: 630390-77-1
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: ZSMVFSDRNHLDQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-methoxy-7-methyl-2H-1-benzopyran-4-one-2-carboxylate 在 palladium on activated charcoal 六甲基磷酰三胺 、 三氟化硼乙醚 、 氢气 、 sodium hydride 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 58.0h， 生成 [(2R,4S)-2-(1-Hydroxy-1-methyl-ethyl)-6-methoxy-7-methyl-chroman-4-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of O-methyl epi-heliannuol E

  摘要：

  A synthesis of the methyl ether of an epimer of the alleochemical heliannuol E is described. The route involves indium mediated allylation of a benzopyranone carboxylate and subsequent one carbon degradation to a vinyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.059
• 作为产物：
  描述：

  1-(2-羟基-5-甲氧基-4-甲基苯基)-乙酮 在 palladium on activated charcoal 甲酸铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 14.0h， 生成 ethyl 6-methoxy-7-methyl-2H-1-benzopyran-4-one-2-carboxylate
  参考文献：
  名称：

  Synthesis of O-methyl epi-heliannuol E

  摘要：

  A synthesis of the methyl ether of an epimer of the alleochemical heliannuol E is described. The route involves indium mediated allylation of a benzopyranone carboxylate and subsequent one carbon degradation to a vinyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.059

文献信息

• Unprecedented C-Methylation at the 2-Position of 2-Carboxy-4-Chromanones – A Case Study with the Corey–Chaykovsky Reagent
  作者：Bishwajit Ganguly、Indrajit Chakraborty、Subrata Ghosh、Nellore Chandar、Debayan Sarkar、Manoj Ghosh

  DOI：10.1055/s-0034-1379203

  日期：——

  An unprecedented C-methylation at the 2-position of 4-chromanone-2-carboxylates was achieved in good yield on treatment with dimethylsulfoxonium methylide. The reaction was performed with excellent chemo- as well as regioselectivity. It is the first synthetic report of alkylation at the 2-position of the chromanone framework through a very mild and simple approach. Such an uncommon behavioral pattern of the Corey-Chaykovsky reagent is justified by theoretical potential energy surface calculations.
• Synthesis of O-methyl epi-heliannuol E
  作者：Subir Kumar Sabui、Ramanathapuram V Venkateswaran

  DOI：10.1016/j.tet.2003.08.059

  日期：2003.10

  A synthesis of the methyl ether of an epimer of the alleochemical heliannuol E is described. The route involves indium mediated allylation of a benzopyranone carboxylate and subsequent one carbon degradation to a vinyl group. (C) 2003 Elsevier Ltd. All rights reserved.