4-(溴甲基)-3-硝基苯甲醛 | 155526-65-1

• 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: 4-(溴甲基)-3-硝基苯甲醛
• 英文名称: 4-(bromomethyl)-3-nitrobenzaldehyde
• 英文别名: Benzaldehyde, 4-(bromomethyl)-3-nitro-
• CAS: 155526-65-1
• 化学式: C₈H₆BrNO₃
• 分子量: 244.045
• InChiKey: BASKWLYIVXTKQV-UHFFFAOYSA-N

物化性质

• 熔点：
  74.5-75.5 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  344.0±32.0 °C(Predicted)
• 密度：
  1.713±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(溴甲基)-3-硝基苯甲醛 在 palladium on activated charcoal 正丁基锂 、 氢气 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 [3-(2-Amino-4-decyl-phenyl)-1-tert-butoxymethyl-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Designed molecules reproducing the two conformations of teleocidins.

  摘要：

  Tumor-promoting teleocidins are known to exist in an equilibrium between two conformational states, the twist form and sofa form, in solution. Benzolactam-Vs, in which the indole ring of indolactams was replaced with a benzene ring, were designed in an attempt to reproduce the active conformation of teleocidins, and synthesized. The 8-membered lactam (benzolactam-V8-310) exists only in the twist form in solution and the 9-membered lactam (benzolactam-V9-310) exists only in the sofa form in solution. The stronger biological activities of the 8-membered lactam than those of indolactam-V and the lack of activity of the 9-membered lactam clearly indicated that active conformation for tumor-promoting activity of teleocidins is close to the twist form.

  DOI：

  10.1016/s0040-4039(00)61468-5
• 作为产物：
  描述：

  4-溴甲基苯甲醛 在 硫酸 、 potassium nitrate 作用下， 反应 4.0h， 以58%的产率得到4-(溴甲基)-3-硝基苯甲醛
  参考文献：
  名称：

  A novel photodegradable hyperbranched polymeric photoresist

  摘要：

  我们报道了第一种光降解型超支化聚缩醛的合成，其中每个重复单元都携带一个光易变的2-硝基苄氧基团。原始的超支化聚缩醛作为一种正性光刻胶，可以用于制作微米尺度的图案；此外，通过将末端基团改为双炔丙基缩醛，可以生成可点击的光图案化基材。

  DOI：

  10.1039/c3cc47048b

文献信息

• A Model for Light-Triggered Porphyrin Anticancer Prodrugs Based on ano-Nitrobenzyl Photolabile Group
  作者：Weiying Lin、Daiwei Peng、Bin Wang、Lingliang Long、Cancheng Guo、Jinbin Yuan

  DOI：10.1002/ejoc.200700972

  日期：2008.2

  A model for light-triggered porphyrin anticancer prodrug 1 was designed and synthesized. Upon photolysis, prodrug 1 can efficiently liberate the anticancer drug tegafur. The MTT assay demonstrates that prodrug 1 is significantly less toxic than its parent drug tegafur, and 1 can release tegafur upon photoactivation in vitro. The light-triggered porphyrin anticancer prodrug technique developed herein

  设计并合成了光触发卟啉抗癌前药 1 的模型。光解后，前药 1 可以有效地释放抗癌药物替加氟。MTT 测定表明前药 1 的毒性明显低于其母体药物替加氟，并且 1 可以在体外光活化后释放替加氟。由于卟啉的肿瘤亲和力和光可控的抗癌药物剂量，本文开发的光触发卟啉抗癌前药技术可能会在化学疗法中找到有用的应用，以最大限度地减少抗癌药物的副作用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Synthesis and UV-irradiation of photocaged nitrobenzyl-BODIPY derivatives
  作者：Sherif Shaban Ragab

  DOI：10.1142/s1088424621500735

  日期：2022.1

  Two different photocaged 2-nitrobenzyl-BODIPY derivatives were designed and synthesized, where the 2-nitrobenzyl phototrigger is either directly attached to the meso position of BODIPY or through a phenoxy linker. The photochemical and photophysical properties of the two constructs were studied and their fluorescence quantum yields were determined. The ultraviolet irradiation of the two photocaged BODIPYs demonstrated a twofold fluorescence enhancement accompanying the uncaging of the BODIPY with the directly attached phototrigger, while the second switchable dyad with the phenoxy linker retains its essentially unaltered emissive behavior.

  我们设计并合成了两种不同的光诱导 2-硝基苄基-BODIPY 衍生物，其中 2-硝基苄基光诱导剂直接连接到 BODIPY 的中间位置或通过苯氧基连接。研究了这两种构建物的光化学和光物理性质，并测定了它们的荧光量子产率。用紫外线照射这两种光笼型 BODIPY，结果表明，直接连接光触发器的 BODIPY 在解除笼型后，荧光增强了两倍，而带有苯氧基连接剂的第二种可切换式二元化合物则保持了基本不变的发射行为。
• Photocleavable and acid cleavable linkers for combinatorial chemistry
  申请人：——

  公开号：US20010025084A1

  公开（公告）日：2001-09-27

  A substrate for solid phase synthesis comprising a solid phase-linker combination of the formula I is disclosed. Also disclosed are processes for preparing the substrate and chemical intermediates useful therein. Among the novel intermediates are compounds of the formula II wherein R 1 is —NO 2 or —CHO; R 2 is —OCH 3 , —CHO or —H; R 3 is chosen from the group consisting of hydroxyl, the residue of a solid support having a plurality of amino groups, and the residue of an ester, and n=1 or 3-12. 1 A substrate of solid phase synthesis of the formula III is also disclosed. 2

  本发明揭示了一种用于固相合成的底物，包括公式I的固相-连接剂组合物。还揭示了制备底物和有用的化学中间体的过程。其中新颖的中间体包括公式II的化合物，其中R1为—NO2或—CHO；R2为—OCH3，—CHO或—H；R3选自羟基、具有多个氨基固体支持的残基和酯的残基，n=1或3-12。还揭示了公式III的固相合成底物。
• Method and apparatus for solid or solution phase reaction under ambient or inert conditions
  申请人：Gubernator Klaus

  公开号：US20050047976A1

  公开（公告）日：2005-03-03

  The present invention generally provides a novel, automation-compatible solid or solution phase reaction vessel, as well as methods for using such a vessel. Generally, the reaction vessel comprises a microplate assembly with a modular solid phase included within the individual reaction wells. The reaction vessel of the invention allows for the integration of solid phase chemistry with the processing abilities of solution phase chemistry. According to the invention, the microplate assembly and the solid phases are configured so as to integrate together into a single reaction vessel. The combination enables solid phase reactions in a single vessel with full compatibility to liquid handling automation. Further, the combination enables novel methods for performing combination solution phase/solid phase reactions under inert conditions.

  本发明一般提供一种新型的、与自动化兼容的固相或溶液相反应容器，以及使用这种容器的方法。一般来说，反应容器包括一个微孔板组件，单个反应孔内包含模块化固相。本发明的反应容器可将固相化学与溶相化学的处理能力相结合。根据本发明，微孔板组件和固相的配置可以整合到一个反应容器中。这种组合可在单个容器中进行固相反应，并与液体处理自动化完全兼容。此外，这种组合还可实现在惰性条件下进行溶液相/固相组合反应的新方法。
• Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins
  作者：Yasuyuki Endo、Michihiro Ohno、Masaaki Hirano、Akiko Itai、Koichi Shudo

  DOI：10.1021/ja953578v

  日期：1996.1.1

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.