4-苄氧基-4'-硝基芪 | 24265-91-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-苄氧基-4'-硝基芪
• 英文名称: 4-benzyloxy-4'-nitrostilbene
• 英文别名: 1-nitro-4-[(E)-2-(4-phenylmethoxyphenyl)ethenyl]benzene
• CAS: 24265-91-6
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: PARNMRYPQGPYSI-VOTSOKGWSA-N

物化性质

• 沸点：
  492.1±14.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-苄氧基-4'-硝基芪 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到4-羟基-4'-硝基二苯乙烯
  参考文献：
  名称：

  Stilbene-based anticancer agents: Resveratrol analogues active toward HL60 leukemic cells with a non-specific phase mechanism

  摘要：

  Several stilbenes, related to known resveratrol, have been synthesized and tested for their anticancer effect on HL60 leukemia cell line, taking particular care of the cell cycle analysis. The most potent compound was the known (Z)-3,4',5-trimethoxystilbene (6b) which was active as apoptotic agent at 0.24 mu M. Differently from other stilbenes (including resveratrol) that induced a prevalent recruitment of cells in S phase of cell cycle, we found a peculiar behavior of 6b that caused a decrease of cells in all phases of cell cycle (G(0)-G(1), S, and G(2)-M) and a proportional increase of apoptotic cells. The potent pro-apoptotic activity shown by compound 6b and its effects on cell cycle make this compound of great interest for further investigations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.028
• 作为产物：
  描述：

  4-羟基-4'-硝基二苯乙烯 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 以71%的产率得到4-苄氧基-4'-硝基芪
  参考文献：
  名称：

  使用催化剂毒物的新型氢化作用：通过添加含氮碱，化学选择性抑制O-苄基保护基的氢解反应

  摘要：

  通过向Pd / C催化的氢化系统中添加适当的含氮碱，可以实现温和的，选择性的，不同于脂肪族和芳香族苄基醚的各种可还原官能团的化学选择氢化方法。

  DOI：

  10.1016/s0040-4020(98)00882-5

文献信息

• Suppression effect of the Pd/C-catalyzed hydrogenolysis of a phenolic benzyl protective group by the addition of nitrogen-containing bases
  作者：Hironao Sajiki、Hiroko Kuno、Kosaku Hirota

  DOI：10.1016/s0040-4039(98)01514-7

  日期：1998.9

  benzyl ester and nitro functionalities distinguishing from the benzyl protective group for the phenolic hydroxyl group has been developed by the employment of 2,2′-dipyridyl as an additive. The suppressive effect on the benzyl ether hydrogenolysis was strongly influenced by the sorts of nitrogen-containing bases employed as an additive.

  通过使用2,2'-联吡啶基作为二甲基吡啶，开发了一种温和的化学选择性氢化方法，该方法使用5％Pd / C的烯烃，N -Cbz，苄基酯和硝基官能团区别于苯酚羟基的苄基保护基。添加剂。对苄基醚氢解的抑制作用受用作添加剂的各种含氮碱的强烈影响。
• Synthesis of alkyloxy stilbenes by one-pot O-alkylation-Wittig and O-alkylation-Wittig–Heck reaction sequence
  作者：Krupa N. Patel、Bola V. Kamath、Ashutosh V. Bedekar

  DOI：10.1016/j.tetlet.2012.10.102

  日期：2013.1

  A new route for the synthesis of allcyloxy stilbenes from hydroxy benzaldehydes is developed by a combination of one-pot reactions. Tandem one-pot O-alkylation-Wittig and O-alkylation-Wittig-Heck reactions offer a simple access to conjugated alkyloxy stilbenes. A highly conjugated tetra(p-alkyloxystyryl) benzene was synthesized from 1,2,4,5-tetrabromobenzene involving a series of one-pot operations following the O-alkylation-Wittig-Heck scheme. (C) 2012 Elsevier Ltd. All rights reserved.
• A novel type of hydrogenation using a catalyst poison: Chemoselective inhibition of the hydrogenolysis for O-benzyl protective group by the addition of a nitrogen-containing base
  作者：Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/s0040-4020(98)00882-5

  日期：1998.11

  A mild and chemoselective hydrogenation method for a variety of reducible functional groups distinguishing from aliphatic and aromatic benzyl ethers was accomplished by the addition of an appropriate nitrogen-containing base to the Pd/C-catalyzed hydrogenation system.

  通过向Pd / C催化的氢化系统中添加适当的含氮碱，可以实现温和的，选择性的，不同于脂肪族和芳香族苄基醚的各种可还原官能团的化学选择氢化方法。
• Stilbene-based anticancer agents: Resveratrol analogues active toward HL60 leukemic cells with a non-specific phase mechanism
  作者：Daniele Simoni、Marinella Roberti、Francesco Paolo Invidiata、Enrico Aiello、Stefania Aiello、Paolo Marchetti、Riccardo Baruchello、Marco Eleopra、Antonietta Di Cristina、Stefania Grimaudo、Nicola Gebbia、Lucia Crosta、Francesco Dieli、Manlio Tolomeo

  DOI：10.1016/j.bmcl.2006.03.028

  日期：2006.6

  Several stilbenes, related to known resveratrol, have been synthesized and tested for their anticancer effect on HL60 leukemia cell line, taking particular care of the cell cycle analysis. The most potent compound was the known (Z)-3,4',5-trimethoxystilbene (6b) which was active as apoptotic agent at 0.24 mu M. Differently from other stilbenes (including resveratrol) that induced a prevalent recruitment of cells in S phase of cell cycle, we found a peculiar behavior of 6b that caused a decrease of cells in all phases of cell cycle (G(0)-G(1), S, and G(2)-M) and a proportional increase of apoptotic cells. The potent pro-apoptotic activity shown by compound 6b and its effects on cell cycle make this compound of great interest for further investigations. (c) 2006 Elsevier Ltd. All rights reserved.