(E)-1-(tert-butyl)-4-(4-nitrostyryl)benzene | 74518-95-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-(tert-butyl)-4-(4-nitrostyryl)benzene
• 英文别名: 1-tert-butyl-4-[(E)-2-(4-nitrophenyl)ethenyl]benzene
• CAS: 74518-95-9
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: OZXHDZCBKOQNGR-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(tert-butyl)-4-(4-nitrostyryl)benzene 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 trans-4'-tert-butyl-4-acetamidostilbene
  参考文献：
  名称：

  代谢N-羟基化。利用取代基变化来调节4-乙酰氨基苯乙二酸酯的体外生物活化。

  摘要：

  N-羟基化是致癌性芳基酰胺生物活化中的重要步骤。该实验室以前的报道表明，反式-4-乙酰氨基二苯乙烯（1）的4​​'取代基的变化对其体外微粒体N-羟基化的速率有显着影响。为了进一步研究电负性和脂肪族取代基的作用，合成了1的4'-CN，4'-CH3、4'-C（CH3）3和4'-CF3类似物，并通过仓鼠进行了代谢转化肝微粒体。每种化合物均以放射性标记形式合成，并通过TLC，质谱和液体闪烁计数对代谢物进行鉴定和定量。4'-CN类似物的N-羟基化的Vmax为24％，Km为1的11％。乙醇酰胺是4'-CN的次要代谢物。-CN化合物。4'-CH3化合物的主要代谢产物是4'-CH2OH衍生物，少量生成N-羟基化产物。类似地，代谢4'-C（CH3）3类似物以产生反式-4'-[2-（羟甲基）-2-丙基] -4-乙酰氨基sti（26）以及痕量的异羟肟酸。4'-CF3底物产生少量的N-羟基化物质，作为唯一可检测的

  DOI：

  10.1021/jm00183a014
• 作为产物：
  描述：

  1-(tert-butyl)-4-((4-nitrophenyl)ethynyl)benzene 在 [RuHCl(CO)(PPh₃)₃] 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以99%的产率得到(E)-1-(tert-butyl)-4-(4-nitrostyryl)benzene
  参考文献：
  名称：

  两室反应器中直接反式选择性钌催化的炔烃还原和连续流动

  摘要：

  据报道，使用可商购的氢化钌配合物，在低氢压力和低反应温度下有效的炔烃的反式选择性氢化。可以耐受各种官能团的发达反应条件是在两室设置下利用异位产生的氢气进行的。反应设置非常适合氘标记。的反式-选择性氢化外推至一个转移氢化协议，采用连续流动仅为10分钟的保留时间的填充床固定化钌氢化催化剂。

  DOI：

  10.1021/acscatal.6b01045

文献信息

• Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (<i>E</i>)-Stilbenes and (1<i>E</i>,3<i>E</i>)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
  作者：Zhao Zhang、Dejiang Zhang、Longzhi Zhu、Dishu Zeng、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.orglett.1c01532

  日期：2021.7.16

  A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The

  公开了一种通用且有效的钯催化的有机锑与苯乙烯的交叉偶联，以得到 ( E )-烯烃。通过使用有机锑试剂，该方法可以以良好的收率和高E / Z制备不对称的 ( E )-1,2-二芳基乙烯和 (1 E ,3 E )-1,4-二芳基丁二烯-1,3-二烯选择性和良好的官能团耐受性。白藜芦醇和 DMU-212 以高产率合成。该协议可以扩展到 (1 E ,3 E ,5 E )-1,6-diphenylhexa-1,3,5-triene的合成,产率为 40%。产品5e、5f和7a 显示出良好的光致发光量子产率，范围为 72% 至 99%。
• Size controlled synthesis of Pd nanoparticles in water and their catalytic application in C–C coupling reactions
  作者：Sudeshna Sawoo、Dipankar Srimani、Piyali Dutta、Rima Lahiri、Amitabha Sarkar

  DOI：10.1016/j.tet.2009.03.062

  日期：2009.5

  Catalytically active Pd nanoparticles have been synthesized in water by a novel reduction of Pd(II) with a Fischer carbene complex where polyethylene glycol (PEG) was used as stabilizer. PEG molecules wrap around the nanoparticles to impart stability and prevent agglomeration, yet leave enough surface area available on the nanoparticle for catalytic activity. Our method is superior to others in terms of rapid generation and stabilization of Pd nanoparticles in water with a cheap, readily available PEG stabilizer. The size of the nanoparticles generated can be controlled by the concentration of PEG in water medium. The size decreased with the increase in the PEG: Pd ratio. This aqueous nano-sized I'd is a highly efficient catalyst for Suzuki, Heck, Sonogashira, and Stille reaction. Water is Used as the only solvent for the coupling reactions. (C) 2009 Elsevier Ltd. All rights reserved.
• The effects of 4′-alkyl substituents on the mutagenic activity of 4-amino- and 4-nitrostilbenes in Salmonella typhimurium
  作者：Björn Ludolph、Markus Klein、Lothar Erdinger、Gernot Boche

  DOI：10.1016/s1383-5718(01)00142-5

  日期：2001.4

  Six derivatives of trans-4-aminostilbene bearing different alkyl groups in the 4'-position and six of the corresponding nitro compounds were synthesized and tested for their mutagenic potency in Salmonella typhimurium strains TA98 and TA100. Regarding the test series in presence of SE-mix, maximum activity was observed for those trans-4-aminostilbenes and trans-4-nitrostilbenes bearing small alkyl substituents like methyl and ethyl. More bulky substituents reduced the mutagenic potential in the order iso-propyl < sec-butyl < tert-butyl for the aminostilbenes. The corresponding nitrostilbenes showed a similar trend under these conditions although the mutagenic activity of the tert-butyl-substituted compound was unexpectedly high in TA100. In the series without metabolic activation the nitrostilbenes showed a continuous decrease of mutagenic activity with the size of the substituents (methyl > ethyl > iso-propyl > sec-butyl > tert-butyl). These trends have been compared with quantitative structure activity relationship (QSAR) model predictions, leading to the conclusion that steric demand is an important factor for mutagenicity of substituted aminostilbenes and nitrostilbenes. The unexpected result for the tert-butyl nitrostilbene tested with metabolic activation may be attributed to a different metabolic pathway. (C) 2001 Elsevier Science B.V. All rights reserved.
• Transition-Metal-Free Catalytic Carboalkoxylation of Styrenes at Room Temperature
  作者：R. Govindarajan、Jasimuddin Ahmed、Asim Kumar Swain、Swadhin K. Mandal

  DOI：10.1021/acs.joc.9b01744

  日期：2019.11.1

  Herein, we describe the first transition-metal-free catalytic carboalkoxylation of styrenes with aryl diazonium salts by Meerwein addition in the presence of a phenalenyl ligand at room temperature without requiring any light stimulation. This three-component reaction allows facile difunctionalization of styrene derivatives with various alcohols (such as 1, 2, and 3 degrees) as the source of alkoxy group during this transformation. The key intermediates and the transition states involved in this reaction path were unraveled by a series of control experiments coupled with density functional theory calculations. The full mechanistic investigation provides an understanding of the selectivity toward carboalkoxylation Meerwein arylation addition elimination) in the presence of various alcohols over the simple arylation to multiple bond (Meerwein arylation-elimination) reaction.