5-(4-nitrophenyl)-2-phenyl-4-(phenylsulfonyl)-2,3-dihydrofuran | 1104732-51-5

• 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: 5-(4-nitrophenyl)-2-phenyl-4-(phenylsulfonyl)-2,3-dihydrofuran
• 英文别名: 4-(Benzenesulfonyl)-5-(4-nitrophenyl)-2-phenyl-2,3-dihydrofuran；4-(benzenesulfonyl)-5-(4-nitrophenyl)-2-phenyl-2,3-dihydrofuran
• CAS: 1104732-51-5
• 化学式: C₂₂H₁₇NO₅S
• 分子量: 407.447
• InChiKey: IBTGWGHNOAUQIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯乙烯 、 2-(苯磺酰基)-1-(4-硝基苯基)乙酮 在 copper diacetate 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 以32%的产率得到5-(4-nitrophenyl)-2-phenyl-4-(phenylsulfonyl)-2,3-dihydrofuran
  参考文献：
  名称：

  Microwave-assisted manganese(III) acetate based oxidative cyclizations of alkenes with β-ketosulfones

  摘要：

  The microwave-assisted synthesis of 5-(4-nitrophenyl)-2-phenyl-4-(phenylsulfonyl)-2,3-dihydrofuran (5a) was performed via manganese(Ill) acetate based oxidative cyclization of 1-(4-nitrophenyl)-2(phenylsulfonyl)ethanone (3a) with vinylbenzene (4a). This new protocol was applied to four sulfone derivatives (3a-d), using vinylbenzene (4a) and diphenylethene (4b), affording a series of 2,3-dihydrofurans (5a-d, 6a-d) in moderate to good yields (26-55%). Similar methodology, applied on allylbenzene (4c), surprisingly, led to dehydronaphthalene derivatives (7a-d) in moderate yields. The unexpected mechanism and the role of allylbenzene (4c) are herein discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.080

文献信息

• Microwave-assisted manganese(III) acetate based oxidative cyclizations of alkenes with β-ketosulfones
  作者：Christophe Curti、Maxime D. Crozet、Patrice Vanelle

  DOI：10.1016/j.tet.2008.10.080

  日期：2009.1

  The microwave-assisted synthesis of 5-(4-nitrophenyl)-2-phenyl-4-(phenylsulfonyl)-2,3-dihydrofuran (5a) was performed via manganese(Ill) acetate based oxidative cyclization of 1-(4-nitrophenyl)-2(phenylsulfonyl)ethanone (3a) with vinylbenzene (4a). This new protocol was applied to four sulfone derivatives (3a-d), using vinylbenzene (4a) and diphenylethene (4b), affording a series of 2,3-dihydrofurans (5a-d, 6a-d) in moderate to good yields (26-55%). Similar methodology, applied on allylbenzene (4c), surprisingly, led to dehydronaphthalene derivatives (7a-d) in moderate yields. The unexpected mechanism and the role of allylbenzene (4c) are herein discussed. (C) 2008 Elsevier Ltd. All rights reserved.