(+/-)-3-hydroxy-3-(4-nitrophenyl)-1-(2'-hydroxy-5'-methoxyphenyl)propan-1-one | 171508-71-7

• 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: (+/-)-3-hydroxy-3-(4-nitrophenyl)-1-(2'-hydroxy-5'-methoxyphenyl)propan-1-one
• 英文别名: 3-Hydroxy-1-(2-hydroxy-5-methoxyphenyl)-3-(4-nitrophenyl)propan-1-one
• CAS: 171508-71-7
• 化学式: C₁₆H₁₅NO₆
• 分子量: 317.298
• InChiKey: WEKFMYOTIINHEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-3-hydroxy-3-(4-nitrophenyl)-1-(2'-hydroxy-5'-methoxyphenyl)propan-1-one 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到2'-hydroxy-5'-methoxy-4-nitrochalcone
  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 在 四氯化钛 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.58h， 生成 (+/-)-3-hydroxy-3-(4-nitrophenyl)-1-(2'-hydroxy-5'-methoxyphenyl)propan-1-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

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.