6-(4-bromophenyl)-4-(4-fluorophenyl)-3-methyl-pyrano[3,4-c]pyran-1,8-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(4-bromophenyl)-4-(4-fluorophenyl)-3-methyl-pyrano[3,4-c]pyran-1,8-dione
• 英文别名: 3-(4-Bromophenyl)-5-(4-fluorophenyl)-6-methylpyrano[3,4-c]pyran-1,8-dione；3-(4-bromophenyl)-5-(4-fluorophenyl)-6-methylpyrano[3,4-c]pyran-1,8-dione
• 化学式: C₂₁H₁₂BrFO₄
• 分子量: 427.226
• InChiKey: AHOBUBWBYSUYBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-(4-bromophenyl)-4-methylsulfanyl-2H-pyran-2-one-3-carbonitrile 、 4-氟苯基丙酮 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以68%的产率得到6-(4-bromophenyl)-4-(4-fluorophenyl)-3-methyl-pyrano[3,4-c]pyran-1,8-dione
  参考文献：
  名称：

  Substituent dependent regioselective synthesis of pyranopyrandiones and 1,2-teraryls from 2H-pyran-2-ones

  摘要：

  The one-pot substituent-directed regioselective synthesis of 1,7-diaryl-2-methyl-4H,5H-pyrano[3,4-c]pyran-4,5-diones 3 as the major and 3,4-diaryl-2-methyl-6-methylsulfanylbenzonitriles 4 as the minor products has been delineated through ring transformation of suitably functionalized 2H-pyran-2-ones 1 with aryl acetones 2. Under similar reaction conditions, 6-aryl-4-sec-amino-2H-pyran-2-ones 5 led, regioselectively, to 3,4-diaryl-2-methyl-6-see-aminobenzonitriles 6. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.084

文献信息

• Substituent dependent regioselective synthesis of pyranopyrandiones and 1,2-teraryls from 2H-pyran-2-ones
  作者：Ramendra Pratap、Diptesh Sil、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2005.05.084

  日期：2005.7

  The one-pot substituent-directed regioselective synthesis of 1,7-diaryl-2-methyl-4H,5H-pyrano[3,4-c]pyran-4,5-diones 3 as the major and 3,4-diaryl-2-methyl-6-methylsulfanylbenzonitriles 4 as the minor products has been delineated through ring transformation of suitably functionalized 2H-pyran-2-ones 1 with aryl acetones 2. Under similar reaction conditions, 6-aryl-4-sec-amino-2H-pyran-2-ones 5 led, regioselectively, to 3,4-diaryl-2-methyl-6-see-aminobenzonitriles 6. (c) 2005 Elsevier Ltd. All rights reserved.
• Substituent-induced regioselective synthesis of 1,2-teraryls and pyrano[3,4-c]pyran-4,5-diones from 2H-pyran-2-ones
  作者：Ramendra Pratap、Brijesh Kumar、Vishnu Ji Ram

  DOI：10.1016/j.tet.2006.06.007

  日期：2006.8

  Substituent-controlled regioselective synthesis of highly functionalized 1,2-teraryls 3a-k has been achieved through ring transformation of 6-aryl-4-(pyrrolidin-1-yl/piperidin-1-yl)-2H-pyran-2-one-3-carbonitriles la-g by aryl acetones 2a-c in the presence of powdered KOH in DMF in very good yield. Under similar reaction conditions, 6-aryl-4-methylsulfanyl-2H-pyran-2-ones 5a-f afforded 1,7-diary'-2-methyl-4H,5H-pyrano[3,4-c]pyran-4,5-diones 6a-j as major products and 3,4-diary'-2-methyl-6-methylsulfanylbenzonitriles as minor constituents 7a-j. (c) 2006 Elsevier Ltd. All rights reserved.