1-(4-nitrophenyl)-2-(4-methoxybenzoyl)allyl benzoate | 1416725-63-7

• 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: 1-(4-nitrophenyl)-2-(4-methoxybenzoyl)allyl benzoate
• 英文别名: [2-(4-Methoxybenzoyl)-1-(4-nitrophenyl)prop-2-enyl] benzoate；[2-(4-methoxybenzoyl)-1-(4-nitrophenyl)prop-2-enyl] benzoate
• CAS: 1416725-63-7
• 化学式: C₂₄H₁₉NO₆
• 分子量: 417.418
• InChiKey: PWTVQFRMTCTREH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(4-methoxyphenyl)prop-2-ynyl benzoate 、 对硝基苯甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以70%的产率得到1-(4-nitrophenyl)-2-(4-methoxybenzoyl)allyl benzoate
  参考文献：
  名称：

  3-芳基-2-乙烯基羧酸酯与苯甲醛之间的独特级联反应导致Morita-Baylis-Hillman加合物的形成

  摘要：

  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。

  DOI：

  10.1021/ol303319a

文献信息

• Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones in human hematological and solid cancer cell lines
  作者：Ieva Karpavičienė、Giedrė Valiulienė、Vytautas Raškevičius、Indrė Lebedytė、Algirdas Brukštus、Visvaldas Kairys、Rūta Navakauskienė、Inga Čikotienė

  DOI：10.1016/j.ejmech.2015.05.012

  日期：2015.6

  A series of alpha-branched alpha,beta-unsaturated ketones were prepared via boron trifluoride etherate mediated reaction between arylalkynes and carboxaldehydes. The evaluation of the antiproliferative activity over hematological (NB4) and solid cancer (A549, MCF-7) cell lines provided a structure-activity relationship. 5-Parameter QSAR equations were built which were able to explain 80%-92% of the variance in activity. The resulting selective lead compound showed IC50 value 0.6 mu M against the hematological cell line and did not cause apoptosis, but blocked cell cycle in G0/G1. Moreover, it was demonstrated that this compound enhances and accelerates retinoic acid induced granulocytic differentiation. (C) 2015 Published by Elsevier Masson SAS.
• 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。