(Z)-2-benzoyl-3-(4-nitrophenyl)allyl acetate | 1416725-49-9

• 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: (Z)-2-benzoyl-3-(4-nitrophenyl)allyl acetate
• 英文别名: [(Z)-2-benzoyl-3-(4-nitrophenyl)prop-2-enyl] acetate
• CAS: 1416725-49-9
• 化学式: C₁₈H₁₅NO₅
• 分子量: 325.321
• InChiKey: KSCYMHLRSJZRDJ-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-phenylprop-2-ynyl acetate 、 对硝基苯甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到(E)-2-benzoyl-3-(4-nitrophenyl)allyl acetate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones

  摘要：

  A series of alpha-branched alpha,beta-unsaturated ketones were prepared in a straightforward manner by the acid catalyzed coupling between arylalkynes and carbaldehydes. The method also allows producing as side product chalcone analogs bearing an additional alpha,beta-unsaturated arylketone in the molecular scaffold. The evaluation of the antiproliferative activity in the human solid tumor cell lines HBL-100 (breast), HBL (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon) provided a structure activity relationship. Overall, the compounds presented active against the resistant cancer cells T-47D. The resulting lead, displaying an unprecedented chalcone scaffold, showed GI(50) values in the range 0.32-0.53 mu M against all cell lines tested. The methoxy group present in the lead might play an important role in the activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.041

文献信息

• A Unique Cascade Reaction between 3-Arylprop-2-inylcarboxylates and Benzaldehydes Leading to the Formation of Morita–Baylis–Hillman Adducts
  作者：Ieva Karpaviciene、Inga Cikotiene

  DOI：10.1021/ol303319a

  日期：2013.1.4

  During an alkyne-carbonyl metathesis reaction between electron-rich 3-arylprop-2-inylcarboxylates and electron-poor benzaldehydes, a smooth migration of carboxylate groups takes place. This unique cascade reaction allows the formation of Morita–Baylis–Hillman (MBH) adducts unavailable via a traditional MBH reaction.

  在富电子的3-芳基丙-2-乙烯基羧酸酯和贫电子的苯甲醛之间的炔烃-羰基复分解反应期间，发生了羧酸酯基团的平稳迁移。这种独特的级联反应可以形成Morita-Baylis-Hillman（MBH）加合物的形成，而这种加合物是通过传统MBH反应无法获得的。