2,4-dimethoxy-β-methyl-β-nitrostyrene | 37629-55-3

• 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: 2,4-dimethoxy-β-methyl-β-nitrostyrene
• 英文别名: (E)-1-(2,4-dimethoxyphenyl)-2-nitropropene；1-(2,4-dimethoxyphenyl)-2-nitropropene；2,4-dimethoxy-1-(2-nitro-cis-propenyl)-benzene；2,4-Dimethoxy-1-(2-nitro-cis-propenyl)-benzol；β-Methyl-β-nitro-2.4-dimethoxystyrol；2,4-dimethoxy-1-[(E)-2-nitroprop-1-enyl]benzene
• CAS: 37629-55-3
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: PCSLZZWXNFQQHN-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-β-methyl-β-nitrostyrene 在 镍 吡啶 、 氢溴酸 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 22.0h， 生成 1-(5-amino-2,4-dihydroxyphenyl)-2-aminopropane dihydrobromide
  参考文献：
  名称：

  In Vivo and in Vitro Studies on the Neurotoxic Potential of 6-Hydroxydopamine Analogs

  摘要：

  In an attempt to determine which physical and biological properties could best be correlated with neurotoxic potential, seven analogs of 1-(2,4,5-trihydroxyphenyl)-2-aminoethane (1), better known as B-hydroxydopamine, were synthesized and compared to 1 in a variety of ways both in vivo and in vitro. The analogs, in combination with-the standard 1, include all eight of the 2,4,5-trisubstituted-phenyl derivatives of phenethylamine and alpha-methylphenethylamine in which the substitution is of the trihydroxy or aminodihydroxy form. Low (60 nmol) and high (300 nmol) intracerebroventricular doses of all analogs produced long-term (7 day) reduction of mouse whole brain norepinephrine (NE) and lesser depletions of dopamine (DA), and effects on serotonin were varied. The analog 1-(5-amino-2,4-dihydroxyphenyl)-2-aminopropane (8) was both more complete and more selective than the standard 1 in depleting NE. Using a histofluorometric glyoxylic acid method and Fink-Heimer silver degeneration stain, it was determined that overt neural degeneration was produced by 8. In vitro, the ease of oxidation of the eight analogs was found to be represented by a formal potential range of -130 to -212 mV vs SCE. However, there was no obvious relationship between ease of oxidation and the extent of monoamine depletion from mouse brain. Using kinetic analysis of synaptosomal accumulation of [H-3]NE and [H-3]DA, it was found that the standard 1 is more potent in its interaction with the DA uptake site (K-i = 12 +/- 0 mu M) than the NE uptake site (K-i = 51 +/- 1 mu M). A correlation analysis was used to determine that differences in NE and DA depletion by each analog could not be explained by differences in potency for in vitro uptake blockade. However, there was a correlation between the K-i for [H-3]NE uptake blockade and the EC(50) for synaptosomal release of preloaded [H-3]NE for the eight analogs (R(2) = 0.96; for log:log plot, R(2) = 0.54), indicating that the results for these two in vitro tests both reflect interaction with the same NE neuronal membrane transport site. A similar correlation between K-i and EC(50) was shown for all eight analogs using [H-3]DA (R(2) = 0.92; for log:log plot, R(2) = 0.52), indicating interaction with the same DA neuronal membrane transport site. These findings demonstrate that there is no single property that can account for selectivity of action and/or potency of catecholamine neurotoxins related to 6-hydroxydopamine.

  DOI：

  10.1021/jm00020a024
• 作为产物：
  描述：

  硝基乙烷 、 2,4-二甲氧基苯甲醛 在 环己胺 作用下， 以35%的产率得到2,4-dimethoxy-β-methyl-β-nitrostyrene
  参考文献：
  名称：

  伯基特淋巴瘤中硝基苯乙烯及相关化合物的合成，抗增殖和促凋亡作用。

  摘要：

  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，

  DOI：

  10.2174/1573406413666171002123907

文献信息

• First synthesis of furo[3,4-<i>c</i>]coumarins
  作者：Dinker I. Brahmbhatt、Jitendra M. Gajera、Chirag N. Patel、Vishwesh P. Pandya、Urvish R. Pandya

  DOI：10.1002/jhet.5570430643

  日期：2006.11

  Various 1,3-dimethyl and 1-methyl-3-phenylfuro[3,4-c]coumarins (5a-h and 6a-h) have been synthesized by demethylation cyclization of the respective 3-aryl-4-ethoxycarbonyl furans (3a-h and 4a-h). These ethoxycarbonyl furans were prepared by reacting appropriate 1-aryl-2-nitro-prop-1-ene (1a-h) with ethyl acetoacetate or ethyl benzoylacetate under Nef reaction condition.

  通过各自的3-芳基-4-乙氧基羰基呋喃（3a）的脱甲基环化反应，合成了各种1,3-二甲基和1-甲基-3-苯基呋喃[3,4- c ]香豆素（5a-h和6a-h）。-h和4a-h）。这些乙氧基羰基呋喃是通过使适当的1-芳基-2-硝基-丙-1-烯（1a-h）与乙酰乙酸乙酯或苯甲酰基乙酸乙酯在Nef反应条件下反应制备的。
• Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael-Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
  作者：Yan Zhang、Pornrapee Vongvilai、Morakot Sakulsombat、Andreas Fischer、Olof Ramström

  DOI：10.1002/adsc.201301033

  日期：2014.3.24

  Dynamic systems based on consecutive thia‐Michael and Henry reactions were generated and transformed using lipase‐catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

  基于脂肪酶催化的不对称转化生成并转化了基于连续的thia-Michael和Henry反应的动力学系统。具有三个连续立体中心的取代的硫烷结构在该过程中以高收率和高对映体过量的方式拆分。
• Contemporary state of the investigation of the influence of the discharge of rivers on the hydrologic structure of the Black Sea
  作者：N. P. Bulgakov、I. Yu. Yurkova

  DOI：10.1007/bf02519260

  日期：2000.11
• Dore,J.-C.; Viel,C., Chimica Therapeutica, 1972, vol. 7, p. 214 - 220
  作者：Dore,J.-C.、Viel,C.

  DOI：——

  日期：——
• GLENNON R. A.; LIEBOWITZ S. M.; ANDERSON III G. M., J. MED. CHEM., 1980, 23, NO 3, 294-299
  作者：GLENNON R. A.、 LIEBOWITZ S. M.、 ANDERSON III G. M.

  DOI：——

  日期：——