4-carboxy-2'-hydroxy-5'-methoxychalcone | 171508-69-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-carboxy-2'-hydroxy-5'-methoxychalcone
• 英文别名: 4-[(E)-3-(2-hydroxy-5-methoxyphenyl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 171508-69-3
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: BYMGJBAITWGMAJ-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-carboxy-2'-hydroxy-5'-methoxychalcone 在 盐酸 、 thallium(I) nitrate 作用下， 以 苯 为溶剂， 反应 20.25h， 生成 (E)-<4'-(methoxycarbonyl)benzylidene>-4,5-dimethoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  A Novel Oxidative Cyclization of 2'-Hydroxychalcones to 4,5-Dialkoxyaurones by Thallium(III) Nitrate

  摘要：

  Scope and mechanism studies are reported on a novel oxidative transformation of certain 2'-hydroxy-5'-methoxychalcones to aurones by thallium(III) nitrate (TTN) in alcoholic solvents. A key feature of the reaction is the incorporation of a solvent-derived alkoxy group at C-4 of the aurone. The thermodynamically more stable Z isomers of the aurones are obtained in all cases. Aurones are formed regardless of whether electron donating or electron attracting groups are present at the para position of the B ring of the starting chalcone.

  DOI：

  10.1021/jo00125a041
• 作为产物：
  描述：

  2'-羟基-5'-甲氧基苯乙酮 、 对甲酰基苯甲酸甲酯 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以59%的产率得到4-carboxy-2'-hydroxy-5'-methoxychalcone
  参考文献：
  名称：

  A Novel Oxidative Cyclization of 2'-Hydroxychalcones to 4,5-Dialkoxyaurones by Thallium(III) Nitrate

  摘要：

  Scope and mechanism studies are reported on a novel oxidative transformation of certain 2'-hydroxy-5'-methoxychalcones to aurones by thallium(III) nitrate (TTN) in alcoholic solvents. A key feature of the reaction is the incorporation of a solvent-derived alkoxy group at C-4 of the aurone. The thermodynamically more stable Z isomers of the aurones are obtained in all cases. Aurones are formed regardless of whether electron donating or electron attracting groups are present at the para position of the B ring of the starting chalcone.

  DOI：

  10.1021/jo00125a041

文献信息

• A Novel Oxidative Cyclization of 2'-Hydroxychalcones to 4,5-Dialkoxyaurones by Thallium(III) Nitrate
  作者：Kshitij Thakkar、Mark Cushman

  DOI：10.1021/jo00125a041

  日期：1995.10

  Scope and mechanism studies are reported on a novel oxidative transformation of certain 2'-hydroxy-5'-methoxychalcones to aurones by thallium(III) nitrate (TTN) in alcoholic solvents. A key feature of the reaction is the incorporation of a solvent-derived alkoxy group at C-4 of the aurone. The thermodynamically more stable Z isomers of the aurones are obtained in all cases. Aurones are formed regardless of whether electron donating or electron attracting groups are present at the para position of the B ring of the starting chalcone.