7-methoxy-5-methoxycarbonyl-2-methylbenzo[b]furan | 200286-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-methoxy-5-methoxycarbonyl-2-methylbenzo[b]furan
• 英文别名: Methyl 7-methoxy-2-methyl-1-benzofuran-5-carboxylate
• CAS: 200286-02-8
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: HIGHEFZHDKCTMV-UHFFFAOYSA-N

物化性质

• 沸点：
  328.3±37.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-5-methoxycarbonyl-2-methylbenzo[b]furan 在 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 过氧化氢苯甲酰 、 sodium hydrogensulfite 作用下， 以 苯 为溶剂， 反应 5.25h， 生成 methyl 3-formyl-4-hydroxy-5-methoxybenzoate
  参考文献：
  名称：

  Ring-Expansion of 2-Methylbenzo[b]furan to 3-Hydroxychromen-4-one: A Potential Approach to a Flavonol Skeleton

  摘要：

  A 2-methylbenzo[b]furan, prepared by the CsF-mediated Claisen rearrangement of a phenyl propargyl ether, could be smoothly transformed into a 3-hydroxychromen-4-one, a potential flavonol skeleton, by three successive treatment with NBS, OsO4, and Na2SO3.

  DOI：

  10.3987/com-97-7947
• 作为产物：
  描述：

  香草酸甲酯 在 potassium carbonate 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 7-methoxy-5-methoxycarbonyl-2-methylbenzo[b]furan
  参考文献：
  名称：

  Cesium Fluoride-mediated Claisen Rearrangements of Phenyl Propargyl Ethers: Substituent Effects of an ortho-Alkoxy Group on the Benzene Ring or Modified Propargyl Residues

  摘要：

  The expected 7-alkoxy-2-methylbenzo [b]furans were effectively given in the CsF-mediated Claisen rearrangement of phenyl propargyl ethers with an o-alkoxy substituent on the benzene ring. On the other hand CsF did not affect the production of the corresponding benzo[b]furans when ethers, carrying a propargyl residue modified by either 1,1-dimethyl or 3-ethoxycarbonyl functions, were used as substrates in the rearrangement.

  DOI：

  10.3987/com-97-7946

文献信息

• Cesium Fluoride-mediated Claisen Rearrangements of Phenyl Propargyl Ethers: Substituent Effects of an ortho-Alkoxy Group on the Benzene Ring or Modified Propargyl Residues
  作者：Tsutomu Ishikawa、Akiko Mizutani、Chizue Miwa、Yumie Oku、Naoko Komano (nee Ohkubo)、Atsuya Takami、Toshiko Watanabe

  DOI：10.3987/com-97-7946

  日期：——

  The expected 7-alkoxy-2-methylbenzo [b]furans were effectively given in the CsF-mediated Claisen rearrangement of phenyl propargyl ethers with an o-alkoxy substituent on the benzene ring. On the other hand CsF did not affect the production of the corresponding benzo[b]furans when ethers, carrying a propargyl residue modified by either 1,1-dimethyl or 3-ethoxycarbonyl functions, were used as substrates in the rearrangement.
• Ring-Expansion of 2-Methylbenzo[b]furan to 3-Hydroxychromen-4-one: A Potential Approach to a Flavonol Skeleton
  作者：Tsutomu Ishikawa、Chizue Miwa

  DOI：10.3987/com-97-7947

  日期：——

  A 2-methylbenzo[b]furan, prepared by the CsF-mediated Claisen rearrangement of a phenyl propargyl ether, could be smoothly transformed into a 3-hydroxychromen-4-one, a potential flavonol skeleton, by three successive treatment with NBS, OsO4, and Na2SO3.