(1α,2α)-di-(2-azaenoyl)-(3β,4β)-di-(4-phenyl)cyclobutane | 1354541-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1α,2α)-di-(2-azaenoyl)-(3β,4β)-di-(4-phenyl)cyclobutane
• 英文别名: (3,4-diphenylcyclobutane-1,2-diyl)bis((1H-pyrrol-2-yl)methanone)
• CAS: 1354541-52-8
• 化学式: C₂₆H₂₂N₂O₂
• 分子量: 394.473
• InChiKey: DEKNYMUIEYHMRB-NVPYSNMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.72
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (2E)-1-phenyl-3-(1H-pyrrol-2-yl)prop-2-en-1-one 在 二苯甲酮 作用下， 以 乙醇 为溶剂， 反应 35.0h， 以49%的产率得到(1α,2α)-di-(2-azaenoyl)-(3β,4β)-di-(4-phenyl)cyclobutane
  参考文献：
  名称：

  Jain, Shubha; Nagwanshi, Rekha; Bakhru, Meena, Journal of the Indian Chemical Society, 2011, vol. 88, # 10, p. 1571 - 1576

  摘要：

  DOI：

文献信息

• Photodimerization of heteroaryl chalcones: comparative antimicrobial activities of chalcones and their photoproducts
  作者：Rekha Nagwanshi、Meena Bakhru、Shubha Jain

  DOI：10.1007/s00044-011-9667-4

  日期：2012.8

  The heterocyclic analogues of chalcones were synthesized by Claisen Schmidt reaction of (a) benzaldehyde with 2-acetylfurane, 2-acetylpyrrole and 2-acetylthiophene and (b) acetophenone with furfural, thiophene-2-carbaldehyde and pyrrole-2-carbaldehyde. The photolysis of class (a) and (b) chalcones under UV lamp gave different products. The stereoselective photodimerization of 1-(furane-2-yl)-3-phenylprop-2-en-1-one (1), 3-phenyl-1-(1H-pyrrole-2-yl)-prop-2-en-1-one (2) gave beta-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (furane-2-yl methanone) (7), (3,4-diphenylcyclobutane-1,2-diyl)bis ((1H-pyrrol-2-yl) methanone) (8) by syn head-to-head coupling whereas 3-phenyl-1-(thiophen-2-yl)-prop-2-en-1-one (3) gave delta-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (thiophen-2-yl methanone) (9) by anti head-to-head coupling. The photolytic products of 3-(furane-2-yl)-1-phenylprop-2-en-1-one (4), 1-phenyl-3-(thiophen-2-yl)-prop-2-en-1-one (5) and 1-phenyl-3-(1H-pyrrole-2-yl)- prop-2-en-1-one (6) were identified as corresponding 1,6-di(furane-2-yl)-3,4-diphenylhexa-1,5-diene-3,4-diol (10), 3,4-diphenyl-1,6-di(thiophen-2-yl)hexa-1,5-diene-3,4-diol (11) and 3,4-diphenyl-1,6-di(1H-pyrrol-2-yl)hexa-1,5-diene-3,4-diol (12) pinacol dimers. The antibacterial and antifungal activity of the precursor chalcones and the dimeric products showed antimicrobial activities of different extents with respect to individual compounds. In general, photolysis of heteroaryl chalcones causes the depletion of antimicrobial activity.