(E)-(N,N-dimethylamino)-4-nitrostyrene | 136795-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(N,N-dimethylamino)-4-nitrostyrene
• 英文别名: N,N-dimethyl-N-[(E)-2-(4-nitrophenyl)-1-ethenyl]amine；(E)-4-nitro-β-(N,N-dimethylamino)styrene；(E)-N,N-dimethyl-2-(4-nitrophenyl)ethenamine；N,N-Dimethyl-2-(4-nitrophenyl)ethenamine
• CAS: 136795-65-8
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: LPBAERIJGIWGFR-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(N,N-dimethylamino)-4-nitrostyrene 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以72%的产率得到对硝基苯甲醛
  参考文献：
  名称：

  A mild method for the conversion of activated aryl methyl groups to carboxaldehydes via the uncatalyzed periodate cleavage of enamines

  摘要：

  A mild procedure for the oxidative cleavage of aryl enamines to aryl aldehydes by periodate without the need for transition metal catalysis is presented.

  DOI：

  10.1016/s0040-4039(00)76515-4
• 作为产物：
  描述：

  4-硝基甲苯 以82%的产率得到
  参考文献：
  名称：

  BIERE H.; RUSSE R., TETRAHEDRON LETT., 1979, NO 16, 1361-1362

  摘要：

  DOI：

文献信息

• Intramolecular interactions in nitroamines studied by 1H, 13C, 15N and 17O NMR spectral and quantum chemical methods
  作者：Ryszard Gawinecki、Erkki Kolehmainen、Robert Dobosz、Hossein Loghmani Khouzani、Subramanian Chandrasekaran

  DOI：10.1007/s13738-013-0269-6

  日期：2014.2

  carbons in 4-(N,N-dimethylamino)-4′-nitrobiphenyl indicate that atoms of the p,p-biphenylene spacer also gain some charge originating from the amino nitrogen. 3 J H,H spin–spin coupling constant shows that among different vinylene compounds, the charge transfer to the nitro group is practically effective only in N,N-dimethyl-2-nitroethenamine where the bond between the vinylene carbons is significantly

  1 H，13 C，15 N和17 O NMR化学位移用于表征Me 2 N-G-NO 2类型的几种硝胺中的分子内相互作用。电荷孤电子对中的氨基的Ñ，Ñ -dimethylnitramine，Ñ，Ñ二甲基-2- nitroethenamine，Ñ，Ñ二甲基p硝基苯胺，4-硝基- β二甲基氨基苯乙烯，4- Ñ，Ñ -二甲基氨基-β-硝基苯乙烯，4-（N，N-二甲基氨基）-4'-硝基联苯和4-（N，N-二甲基氨基）-4′-亚硝基二苯乙烯不仅转移到硝基氧上，而且转移到G间隔基的亚乙烯基和苯碳上，也转移到N-甲基碳上。发现减少的核屏蔽在质量上与核周围原子电荷的减少有关。通过将NMR数据与从头算量子化学计算获得的结果进行比较，进一步证实和量化了这一发现。当相互作用的NMe 2和NO 2基团被短的间隔基隔开时，17 O NMR化学位移变化似乎更为明显。另一方面，15N NMR化学位移表明，氨基氮上电荷的减少与间隔基的长度无关。在17
• An Efficient One-Step Method for the Conversion of β-(Dimethylamino)sty­renes into Arylacetonitriles
  作者：Alexey M. Starosotnikov、Alexander V. Lobach、Svyatoslav A. Shevelev

  DOI：10.1055/s-2005-918405

  日期：——

  A new simple and efficient one-step method for the preparation of arylacetonitriles by reaction of β-(dimethylamino)styrenes with hydroxylamine hydrochloride in formic acid solution is described.

  介绍了一种简便高效的一步法，通过β-(二甲氨基)苯乙烯与盐酸羟胺在甲酸溶液中的反应来制备苯乙腈。
• Enamines in Heterocyclic Synthesis: A Route to 4-Substituted Pyrazoles and Condensed Pyrazoles
  作者：Huwaida M. E. Hassaneen、Hamdi M. Hassaneen、Mohamed H. Elnagdi

  DOI：10.1515/znb-2004-1009

  日期：2004.10.1

  The reaction of nitrile imines, generated in situ, from hydrazonoyl halides 3a - e with enamines 2a - c affords pyrazoles 8a - g. These pyrazoles have been used to prepare condensed pyrazoles.

  标题：摘要 通过将在原位生成的腈亚胺与烯胺反应，可以得到吡唑化合物。这些吡唑化合物已被用于制备缩合吡唑。
• Studies with enamines: Reactivity of<i>N,N</i>-dimethyl-<i>N</i>-[(<i>E</i>)-2-(4-nitrophenyl)-1-ethenyl]amine towards nitrilimine and aromatic diazonium salts
  作者：Hamad M. Al-Matar、Sayed M. Riyadh、Mohamed H. Elnagdi

  DOI：10.1002/jhet.5570440315

  日期：2007.5

  In the presence of triethylamine, cycloaddition reaction of enamine 1 with hydrazonoyl halides 2 followed by dimethylamine elimination was achieved, yielding the corresponding 1,3,4-trisubstituted pyrazoles 4. Coupling of enamine 1 with aromatic diazonium salts afforded 2-(arylhydrazono)-2-(4-nitrophenyl)acetaldehyde 9 in good yield. Refluxing the phenyl hydrazone 9a with chloroacetone in ethanol in

  在三乙胺的存在下，烯胺1与酰卤2进行环加成反应，然后消除二甲胺，得到相应的1,3,4-三取代的吡唑4。烯胺1与芳族重氮盐的偶联以良好的收率得到2-（芳基肼基）-2-（4-硝基苯基）乙醛9。在三乙胺的存在下，将苯9a与氯丙酮在乙醇中回流，得到经由中间体11a形成的1,3,5-三取代的吡唑12a 。9a的反应在无水乙酸钠存在下，用盐酸羟胺与乙醇反应，得到肟13a，将其在乙酸中在微波炉中辐照，得到15a和16a的混合物。
• Surmounting the resistance against EGFR inhibitors through the development of thieno[2,3-d]pyrimidine-based dual EGFR/HER2 inhibitors
  作者：Sandra N. Milik、Amal Kamal Abdel-Aziz、Deena S. Lasheen、Rabah A.T. Serya、Saverio Minucci、Khaled A.M. Abouzid

  DOI：10.1016/j.ejmech.2018.06.011

  日期：2018.7

  In light of the emergence of resistance against the currently available EGFR inhibitors, our study focuses on tackling this problem through the development of dual EGFR/HER2 inhibitors with improved enzymatic affinities. Guided by the binding mode of the marketed dual EGFR/HER2 inhibitor, Lapatinib, we proposed the design of dual EGFR/HER2 inhibitors based on the 6-phenylthieno[2,3-d]pyrimidine as a core scaffold and hinge binder. After two cycles of screening aiming to identify the optimum aniline headgroup and solubilizing group, we eventually identified 27b as a dual EGFR/HER2 inhibitor with IC50 values of 91.7 nM and 1.2 mu M, respectively. Notably, 27b dramatically reduced the viability of various patient-derived cancer cells preferentially overexpressing EGFR/HER2 (A431, MDA-MBA-361 and SKBr3 with IC50 values of 1.45, 3.5 and 4.83 mu M, respectively). Additionally, 27b efficiently thwarted the proliferation of lapatinib-resistant human non-small lung carcinoma (NCI-H1975) cells, harboring T790 M mutation, with IC50 of 4.2 mu M. Consistently, 27b significantly blocked EGF-induced EGFR activation and inactivated its downstream AKT/mTOR/S6 signalling pathway triggering apoptotic cell death in NCI-H1975 cells. The present study presents a promising candidate for further design and development of novel EGFR/HER2 inhibitors capable of overcoming EGFR TKIs resistance. (C) 2018 Elsevier Masson SAS. All rights reserved.