(4,5-dimethoxy-2-nitrophenyl)methanamine | 123330-73-4

• 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: (4,5-dimethoxy-2-nitrophenyl)methanamine
• 英文别名: 4,5-dimethoxy-2-nitrobenzylamine；4,5-dimethoxy-2-nitro-benzylamine；4,5-Dimethoxy-2-nitro-benzylamin
• CAS: 123330-73-4
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: FEKSGKBBJQTYRY-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  365.8±37.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4,5-dimethoxy-2-nitrophenyl)methanamine 以 水 、 乙腈 为溶剂， 生成 6-硝基藜芦醛
  参考文献：
  名称：

  Biologically useful chelators that take up calcium(2+) upon illumination

  摘要：

  DOI：

  10.1021/ja00202a042
• 作为产物：
  描述：

  4,5-dimethoxy-2-nitrobenzyl phthalimide 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 (4,5-dimethoxy-2-nitrophenyl)methanamine
  参考文献：
  名称：

  Synthesis, stability and optimized photolytic cleavage of 4-methoxy-2-nitrobenzyl backbone-protected peptides

  摘要：

  我们展示了4-甲氧基-2-硝基苯甲基作为与Boc化学兼容的完全可逆骨架修饰在合成肽中的潜力。

  DOI：

  10.1039/b600304d

文献信息

• Enzymatic Synthesis of Caged NADP Cofactors:  Aqueous NADP Photorelease and Optical Properties
  作者：Charles P. Salerno、Douglas Magde、Andrew P. Patron

  DOI：10.1021/jo9917846

  日期：2000.6.1

  The synthesis of caged NADP analogues 18, 19, and 20 has been accomplished by utilizing the transglycosidase activity of solubilized NAD glycohydrolase (porcine brain) to incorporate caged nicotinamides 2, 3, and 4 into NADP. The synthesis of several nicotinamides modified at the carboxamide with o-nitrobenzyl photolabile groups is demonstrated as well as their potential for enzymatic transglycosidation

  笼状NADP类似物18、19和20的合成已通过利用溶解的NAD糖水解酶（猪脑）的转糖苷酶活性将笼状烟酰胺2、3和4掺入NADP来完成。已证明了在羧酰胺上被邻硝基苄基光不稳定基团修饰的几种烟酰胺的合成及其酶促糖苷化的潜力。这些结果进一步证明了将位阻底物直接酶促糖苷化成NAD（P）的可行性，尽管发现高烟酰胺类似物水溶性是某些类似物提高产量的必要特征。在水性条件下调查笼中类似物的净NADP光释放量，同时评估了类似物及其光副产物的紫外和荧光特性，以与依赖于光学监测酶活性的系统的相容性。开发了高度水溶性的α-甲基-o-硝基苄基8，用于合成20，以提高净NADP的光释放。化合物20表现出高的75％净NADP光释放，而没有大量的紫外线光学发黑或荧光副产物。ESI / MALDI-MS显示类似物18和19主要光生NADP的加合物，具有有害的紫外线和荧光特性。我们的工作强调了α-甲基取代赋予羧酰胺水溶液从邻
• Photolysis of ortho-nitrobenzylic derivatives: the importance of the leaving group
  作者：Tomáš Šolomek、Sébastien Mercier、Thomas Bally、Christian G. Bochet

  DOI：10.1039/c1pp05308f

  日期：2012.3

  Quantum yields for the photoinduced release of seven different commonly used leaving groups (LGs) from the o-nitroveratryl protecting group were measured. It was found that these quantum yields depend strongly on the nature of the LGs. We show that the quantum efficiency with which the LGs are released correlates with the stabilization that these LGs provide to o-nitrobenzyl-type radicals because radical stabilizing groups weaken the C–H bond that is cleaved in the photoinduced hydrogen atom transfer step, and hence lower the barrier for this process. At the same time these substituents lower the endothermicity of the thermal hydrogen atom transfer and thus increase the barrier for the reverse process, thereby enhancing the part of the initially formed aci-nitro intermediates which undergo cyclization (which ultimately leads to LG release). Radical stabilization energies computed by DFT methods are thus a useful predictor of the relative efficiency with which LGs are photoreleased from o-nitrobenzyl protecting groups.

  测量了邻硝基藜芦碱保护基团光诱导释放七个不同常用离去基团（LG）的量子产率。结果发现，这些量子产率在很大程度上取决于 LG 的性质。我们的研究表明，LGs 释放的量子效率与这些 LGs 为邻硝基苄基自由基提供的稳定作用有关，因为自由基稳定基团会减弱在光诱导氢原子转移步骤中被裂解的 C-H 键，从而降低这一过程的障碍。同时，这些取代基降低了氢原子热转移的内热，从而增加了反向过程的障碍，因此增加了最初形成的酰硝基中间体发生环化（最终导致 LG 释放）的部分。因此，通过 DFT 方法计算出的自由基稳定能可以有效预测 LG 从邻硝基苄基保护基团中光释放的相对效率。
• Caged Dexamethasone to Photo‐control the Development of Embryos through Activation of the Glucocorticoid Receptor
  作者：Mrinal Mandal、Pierluigi Scerbo、Ian Coghill、Jean‐François Riou、Christian G. Bochet、Bertrand Ducos、David Bensimon、Thomas Le Saux、Isabelle Aujard、Ludovic Jullien

  DOI：10.1002/chem.202400579

  日期：2024.4.22

  Efficient tools for controlling molecular functions with exquisite spatiotemporal resolution are much in demand to investigate biological processes in living systems. Here we report an easily synthesized caged dexamethasone for photo‐activating cytoplasmic proteins fused to the glucocorticoid receptor. In the dark, it is stable in vitro as well as in vivo in both zebrafish (Danio rerio) and Xenopus sp, two significant models of vertebrates. In contrast, it liberates dexamethasone upon UV illumination, which has been harnessed to interfere with developmental steps in embryos of these animals. Interestingly, this new system is biologically orthogonal to the one for photo‐activating proteins fused to the estrogen ERT receptor, which brings great prospect for activating two distinct proteins down to the single cell level.

  摘要 在研究生命系统中的生物过程时，非常需要能以精确的时空分辨率控制分子功能的高效工具。在此，我们报告了一种易于合成的笼式地塞米松，用于光激活与糖皮质激素受体融合的细胞质蛋白。在黑暗中，它在斑马鱼（Danio rerio）和爪蟾（Xenopus sp）这两种重要的脊椎动物模型的体外和体内都是稳定的。与此相反，它在紫外线照射下会释放地塞米松，从而干扰这些动物胚胎的发育步骤。有趣的是，这一新系统与融合了雌激素 ERT 受体的光激活蛋白在生物学上是正交的，这为激活两种不同的蛋白直至单细胞水平带来了巨大的前景。
• Application of the Amidomethylation Reaction to the Synthesis of Quinazolines
  作者：Alan M. Downes、Francis Lions

  DOI：10.1021/ja01163a070

  日期：1950.7
• Biologically useful chelators that take up calcium(2+) upon illumination
  作者：S. R. Adams、J. P. Y. Kao、R. Y. Tsien

  DOI：10.1021/ja00202a042

  日期：1989.9