1-(4-甲氧基苯基)-1-(4-硝基苯基)乙烯 | 28358-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-甲氧基苯基)-1-(4-硝基苯基)乙烯
• 英文名称: 1-methoxy-4-(1-(4-nitrophenyl)vinyl)benzene
• 英文别名: 1-[1-(4-Methoxyphenyl)ethenyl]-4-nitrobenzene
• CAS: 28358-68-1
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: HDXDUVASPAOWCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1-(4-甲氧基苯基)-1-(4-硝基苯基)乙烯 在 9,10-二氰基蒽 、 氧气 作用下， 以 乙腈 为溶剂， 生成 3,6-bis(4-methoxyphenyl)-3,6-bis(-4-nitrophenyl)-1,2-dioxane
  参考文献：
  名称：

  通过解离电子转移到3,3,6,6-四芳基-1,2-二恶烷的高效均相自由基-阴离子链反应

  摘要：

  通过使用循环伏安法，恒电位电解和数字仿真，在惰性电极上研究了一系列3,3,6,6-四芳基-1,2-二恶烷（TAD）。该系列由苯基取代的TAD（1 a），对-甲氧基-芳基TAD（1 b，1 c）和对-甲氧基/硝基-TAD（1 d）组成。）。异质电子转移（ET）的还原是解离的，导致氧-氧键断裂，产生一个二元自由基阴离子，后者可以通过β断裂或ET竞争性地反应。二硅基自由基阴离子的裂解产生烯烃，取代的二苯甲酮和二苯甲酮自由基阴离子。二苯甲酮自由基阴离子可传播有效的均相ET断裂链反应，这说明了产物比率的电势依赖性和在受控电势电解实验中观察到的低电荷消耗。实验循环伏安图的数字模拟可用于估计异构ET对O的速率常数O键，以及迪斯通自由基阴离子的β断裂片段化的速率常数。密度泛函理论计算证实了初始离解ET异质动力学的差异。内过氧化物1 a – 1 c主要通过协同的解离ET机制反应，尽管数据表明逐步解离途径也具有竞争性。1

  DOI：

  10.1002/chem.200902023
• 作为产物：
  描述：

  对硝基苯乙酮 在 sodium 2'-(dicyclohexylphosphanyl)-2,6-diisopropylbiphenyl-4-sulfonate 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 生成 1-(4-甲氧基苯基)-1-(4-硝基苯基)乙烯
  参考文献：
  名称：

  迈向更绿色的Barluenga-Valdés交叉偶联：微波促进的Pd / PEG / H 2 O可循环催化体系的C–C键形成。

  摘要：

  已开发出一种绿色的Barluenga-Valdés交叉偶联反应，利用钯催化合成1,1-二芳基乙烯。发现在微波辐射下，基于PEG / H 2 O中Pd / Xphos-SO 3 Na或Pd / MeDavephos-CF 3 SO 3的新催化体系是该转化的最佳条件。还对钯催化剂体系的可回收性进行了研究，发现钯催化剂体系在九次运行中均具有活性，而活性没有明显损失。

  DOI：

  10.1021/acs.orglett.9b03310

文献信息

• [EN] METHOD FOR INHIBITION OF DEUBIQUITINATING ACTIVITY<br/>[FR] MÉTHODE D'INHIBITION DE L'ACTIVITÉ DE DÉSUBIQUITINATION
  申请人：VIVOLUX AB

  公开号：WO2013058691A1

  公开（公告）日：2013-04-25

  A compound of the general structure (I) is capable of abrogating the deubiquitinating (DUB) activity of the 19S RP DUBs. The compound can be used for treating cancer, in particular of cancer refractory to treatment by state-of-the-art chemotherapy. Also disclosed are corresponding methods of treatment and a pharmaceutical composition comprising the compound.

  一种具有一般结构（I）的化合物能够废除19S RP DUBs的去泛素化（DUB）活性。该化合物可用于治疗癌症，特别是对于无法通过最先进化疗治疗的癌症。还公开了相应的治疗方法和包含该化合物的药物组合物。
• Hydroarylation of terminal alkynes with arylboronic acids catalyzed by low loadings of palladium
  作者：Lei Xu、Shiyu Li、Qi Zhang、Ning Deng、Biao Zhang、Huajian Xu

  DOI：10.1016/j.cclet.2022.05.048

  日期：2023.2

  The hydroarylation reaction of terminal alkynes with arylboronic acids catalyzed by low (400 ppm) loadings of palladium has been developed. The reaction is broad in scope and high-yielding, even on multi-gram scale. It is suitable for the synthesis of alkenes labeled with deuterium, and for the late-stage modification of bioactive molecules.

  已经开发了由低负载量 (400 ppm) 钯催化的末端炔烃与芳基硼酸的加氢芳基化反应。该反应范围广，产量高，甚至在多克规模上也是如此。适用于氘标记烯烃的合成，以及生物活性分子的后期修饰。
• 10.1039/d4sc01905a
  作者：Joseph, Ebbin、Brar, Deshkanwar S.、Stuhlsatz, Gaven、Tunge, Jon A.

  DOI：10.1039/d4sc01905a

  日期：——

  synthesis of alkenes is highly significant due to their extensive applications in both synthetic and polymer industries. A transition metal-free approach has been devised for the chemoselective olefination of carboxylic acid salts. This modular approach provides direct access to valuable electron-deficient styrenes in moderate to good yields. Detailed mechanistic studies suggest anionic decarboxylation is followed

  由于烯烃在合成和聚合物工业中的广泛应用，具有成本效益和高效的合成烯烃具有非常重要的意义。已经设计了一种无过渡金属的方法用于羧酸盐的化学选择性烯化。这种模块化方法可以以中等至良好的产率直接获得有价值的缺电子苯乙烯。详细的机理研究表明阴离子脱羧之后是卤素离子转移。这种卤素转移导致反应物电子的反极化，从而实现限速反弹消除。
• Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck–Mizoroki Reaction
  作者：Diego A. Alonso、Carmen Nájera、Ma Carmen Pacheco

  DOI：10.1002/1615-4169(200202)344:2<172::aid-adsc172>3.0.co;2-9

  日期：2002.2

  Oxime-derived, chloro-bridged palladacycles 16 are efficient complexes for the Heck vinylation of aryl halides. The isolated catalysts are thermally stable, not sensitive to air or moisture and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions, with aryl iodides, bromides and chlorides with acrylic esters and olefins displaying turnover numbers (TON) of up to 10(10) for phenyl iodide and turnover frequencies (TOF) of 1.4 x 10(8) h(-1). Deactivated aryl bromides undergo the Heck reaction with styrene with TON and TOF values up to 97,000 and 6063 h-1, respectively. Even aryl chlorides undergo the coupling reaction with olefins with TON up to 920. Complexes 16 catalyze the synthesis of 2,3-disubstituted indenones and indoles in good yields via annulation reaction of internal alkynes with o-bromo- or o-chlorobenzaldehyde and o-iodoaniline, respectively.
• Substituent-dependent electron-transfer-induced photooxygenation of 1,1-diarylethylenes
  作者：Klaus Gollnick、Albert Schnatterer、Gerald Utschick

  DOI：10.1021/jo00074a035

  日期：1993.10

  Rates and products of 9,10-dicyanoanthracene-sensitized photooxygenations of 1,1-diarylethylenes (1a-r) in acetonitrile were studied. If at least one of the aryl groups carries an electron-donating substituent at the para (or ortho) position (1a-1), 3,3,6,6-tetraaryl-1,2-dioxanes (2a-1) are generated in high yields (85-100%). Benzophenones (3) are the only other observable products. 1,1-Diphenylethylene (1n) and its m-methoxy (1m), p-chloro (1q,p), and p-nitro (1q,r) derivatives,however, yield mainly benzophenones (3m-r) (>50%) (the p-nitro compounds only in the presence of biphenyl). 1,2-Dioxanes (2m-p), cyclobutanes (4n-p), and alpha-tetralones (5m-o) are obtained as side products. Dioxanes, benzophenones, and alpha-tetralones are products of electron-transfer induced oxygenations involving triplet ground-state molecular oxygen, O-3(2). Singlet molecular oxygen, O2(1DELTA(g)),contributes to the benzophenone formation from strongly electron-donor substituted diarylethylenes. An exception is the most powerful electron-donor substituted diarylethylene 1a, with which O2(1DELTA(g)) undergoes an electron-transfer reaction affording dioxane 2a. Dioxane formation proceeds via free-radical cations 1.+, which enter into a chain reaction with 1, O-3(2), and another molecule of 1 to yield dioxane 2 and a new radical cation 1.+ that maintains the chain reaction. The efficiency of this chain process, however, is found to be several orders of magnitude smaller than expected. To explain this result, a 1,6-biradical.1-1-O2.is proposed to be generated in this chain reaction as the product-determining intermediate that predominantly fragments into O-3(2) and two molecules of 1. Cyclization to dioxane 2 and transformation to benzophenone 3 occur at presumably less than 0.1% from this biradical. The pathways leading to cyclobutanes (4) and alpha-tetralones (5) are also discussed.