2-硝基-1-苯基丙烯 | 86255-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-硝基-1-苯基丙烯
• 英文名称: 1-(2,4,5-trimethoxyphenyl)-2-nitroethene
• 英文别名: 2,4,5-Trimethoxy-β-nitrostyrol；trans-β-nitro-2.4.5-trimethoxy-styrene；trans-β-Nitro-2.4.5-trimethoxy-styrol；1,2,4-Trimethoxy-5-[(e)-2-nitrovinyl]benzene；1,2,4-trimethoxy-5-[(E)-2-nitroethenyl]benzene
• CAS: 86255-45-0
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: DPZJDIXHUBSWDS-SNAWJCMRSA-N

物化性质

• 沸点：
  391.6±37.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、DCM、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-硝基-1-苯基丙烯 在 sodium dithionate 、 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.25h， 生成 1-(2,5-dihydroxy-4-methoxyphenyl)-2-<(tert-butoxycarbonyl)amino>ethane
  参考文献：
  名称：

  Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine

  摘要：

  In an attempt to evaluate the possible relationship between the neurotoxicity of 6-hydroxydopamine and the redox properties and electrophilic reactivity of the 6-hydroxydopamine-p-hydroquinone/p-quinone system, we have synthesized a series of 6-hydroxydopamine analogues in which the C4-hydroxy group is replaced with various electron-donating and electron-withdrawing substituents. With the aid of cyclic voltammetry, the formal oxidation potentials (E degrees ') for the p-hydroquinone/p-quinone redox couples and the rates of cyclization of the p-quinones to the corresponding p-iminoquinones were determined. As expected, electron-rich p-hydroquinones were easily oxidized to the p-quinones, which underwent cyclization slowly, whereas the oxidation of electron-poor p-hydroquinones required higher voltages and yielded p-quinones, which cyclized readily at pH 7.4. The neurotoxic potential of these compounds showed that in vivo destruction of noradrenergic terminals, as measured by inhibition of norepinephrine uptake by rat heart slices, occurred only with those analogues bearing electron-donating substituents. Potent neurotoxic properties were associated only with the 4-amino and 4-hydroxy derivatives, both of which form p-quinones, which do not cyclize readily at pH 7.4. These results support the thesis that the p-quinone derived from 6-hydroxydopamine may be an important species in the mediation of the neurodestruction caused by 6-hydrodopamine.

  DOI：

  10.1021/jm00370a014
• 作为产物：
  描述：

  1-(二甲氨基)-2-硝基乙烯 以36%的产率得到
  参考文献：
  名称：

  BUECHI G.; MAK C.-P., J. ORG. CHEM. , 1977, 42, NO 10, 1784-1786

  摘要：

  DOI：

文献信息

• Synthesis of 3-Substituted 2-Aminonaphtho[2,3-<i>b</i>]furan-4,9-diones from 2-Hydroxy-1,4-Naphthoquinone and Nitroalkenes
  作者：Manoj R. Zanwar、Veerababurao Kavala、Sachin D. Gawande、Chun-Wei Kuo、Ting-Shen Kuo、Mei-Ling Chen、Chiu-Hui He、Ching-Fa Yao

  DOI：10.1002/ejoc.201300996

  日期：2013.12

  The efficient base-catalyzed synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-dione derivatives from readily available precursors such as 2-hydroxy-1,4-naphthoquinone and nitroalkenes under aqueous conditions is described. Interesting features of this methodology are the conversion of a nitro functionality into an amino functionality in the absence of a reducing agent and the development of

  描述了在水性条件下从容易获得的前体（例如 2-羟基-1,4-萘醌和硝基烯烃）有效碱催化合成 3-取代 2-氨基萘[2,3-b]呋喃-4,9-二酮衍生物. 这种方法的有趣特征是在没有还原剂的情况下将硝基官能团转化为氨基官能团，并开发了一种三组分反应，用于从醛、2-羟基-1,4-萘醌和硝基甲烷。
• Synthesis, Antiproliferative and Pro-Apoptotic Effects of Nitrostyrenes and Related Compounds in Burkitt's Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、Darren Fayne、James P. McKeown、Thomas McCabe、Brendan Twamley、Clive Williams、Mary J. Meegan

  DOI：10.2174/1573406413666171002123907

  日期：2018.2.6

  identified as a lead target structure for the development of particularly effective compounds targeting Burkitt's lymphoma (BL). OBJECTIVES The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt's lymphoma (BL). METHODS A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions.

  背景技术淋巴细胞癌（淋巴瘤）约占全世界恶性疾病的12％。硝基苯乙烯支架被认为是开发针对Burkitt淋巴瘤（BL）的特别有效的化合物的主要靶标结构。目的目前的研究目的是合成一组硝基苯乙烯化合物并评估其在伯基特氏淋巴瘤（BL）中的活性。方法使用Henry Knoevenagel缩合反应设计和合成一组结构变化的化合物。单晶X射线分析证实了这些新颖结构的六个实例的E构型。还研究了许多与硝基苯乙烯有关的化合物，包括1，3-双（芳基）-2-硝基丙烯与含有硝基乙烯基药效团的杂环支架，例如3-硝基-2-苯基-2H-色烯。使用BL细胞系EBV-MUTU-1和EBV + DG-75（耐化学性）评估化合物的抗增殖活性，以建立初步的结构活性关系。结果成功建立了具有优化的硝基苯乙烯骨架和3-硝基-2-苯基-2Hchromne结构的铅化合物，在MUTU-1细胞中的典型IC50值分别为0.45 µM和0.47 µM，
• Nitromethane as a surrogate cyanating agent: 7-<i>N</i>,<i>N</i>-dimethylamino-4-hydroxycoumarin-catalyzed, metal-free synthesis of α-iminonitriles
  作者：Iddum Satyanarayana、Kiran B. Manjappa、Ding-Yah Yang

  DOI：10.1039/d0gc03411h

  日期：——

  kinetically controlled, base-mediated and 1,3-diketone-catalyzed reaction is reported. The preparation of target compounds was realized by condensation of substituted anilines and aldehydes in nitromethane as a surrogate cyanating agent and as a solvent. This strategy was further improved by replacing aldehydes and nitromethane with β-nitrostyrene and ethanol, respectively, rendering the methodology greener

  报道了一种通过动力学控制的，碱介导的和1,3-二酮催化的反应合成α-亚胺的有效的无金属/碱金属氰化物的方法。通过将取代的苯胺和醛在硝基甲烷中作为替代氰化剂和溶剂缩合，可以实现目标化合物的制备。通过分别用β-硝基苯乙烯和乙醇代替醛和硝基甲烷，进一步改善了该策略，从而使该方法更加环保。研究了7，N，N-二甲基氨基-4-羟基香豆素等1，3-二酮在该三组分反应中的催化作用，并在控制实验的基础上提出了可能的机理。
• The Preparation of Potentially Psychoactive β-Alkoxyphenethylamines
  作者：Milton Aillón. Torres、Bruce Cassels、Macros C. Rezende

  DOI：10.1080/00397919508012687

  日期：1995.4

  Abstract The preparation of β-alkoxyphenethylamines 3 is described. As part of our interest in structure-activity relationships of psychotomimetic phenethylamines 1 and their interactions with serotoninergic receptors 2, we describe in the present communication the preparation of a series of substituted β-alkoxyphenylethylamines. A few of these compounds had been prepared before 3,4 and their psychotropic

  摘要 描述了β-烷氧基苯乙胺3 的制备。作为我们对拟精神病苯乙胺 1 的构效关系及其与 5-羟色胺能受体 2 相互作用的兴趣的一部分，我们在本通讯中描述了一系列取代的 β-烷氧基苯乙胺的制备。这些化合物中的一些在 3,4 之前就已制备出来，并且它们的精神药物特性已在人类志愿者身上得到了描述。然而，除了少数情况下，β-甲氧基化衍生物显示出与母体化合物相似或略大于母体化合物的效力之外，此后没有对这些新化合物进行药理学研究。对致幻性苯乙胺侧链 β 位取代的影响知之甚少，
• Pd-catalyzed cross-coupling of carboxylic acids with nitroethane via combination of decarboxylation and dehydrogenation
  作者：Min Zhang、Jun Zhou、Jian Kan、Min Wang、Weiping Su、Maochun Hong

  DOI：10.1039/c0cc01029d

  日期：——

  An unexpected coupling reaction of arene carboxylic acid with nitroethane via a combination of decarboxylation and dehydrogenation is described. The method provides exclusively (E)-beta-nitrostyrenes.

  描述了芳烃羧酸与硝基乙烷通过脱羧和脱氢的组合的意外偶联反应。该方法仅提供（E）-β-硝基苯乙烯。