1-(1-bromoethyl)-4,5-dimethoxy-2-nitrobenzene | 144619-12-5

• 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: 1-(1-bromoethyl)-4,5-dimethoxy-2-nitrobenzene
• 英文别名: 1-(4,5-dimethoxy-2-nitrophenyl)ethyl bromide；a-Methyl-2-nitro-4,5-dimethoxybenzyl bromide
• CAS: 144619-12-5
• 化学式: C₁₀H₁₂BrNO₄
• 分子量: 290.114
• InChiKey: QNRKIJIYNLQARX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1-(1-bromoethyl)-4,5-dimethoxy-2-nitrobenzene 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 4-(4',5'-dimethoxy-α'-methyl-2'-nitrobenzyloxy)-3,5-dimethylbenzyl alcohol
  参考文献：
  名称：

  Hydrolytic Stabilization of Protected p-Hydroxybenzyl Halides Designed as Latent Quinone Methide Precursors

  摘要：

  The hydrolysis rates of a series of protected p-hydroxybenzyl halides designed to generate a p-quinone methide through 1,6-elimination following photolytic deprotection have been investigated in order to optimize hydrolytic stability. A number of p-hydroxybenzyl halides containing an ether-or carbonate-linked photolabile hydroxy protecting group and a fluoride, chloride, or bromide benzylic leaving group have been synthesized. The hydrolysis rates of these derivatives in different water/acetonitrile mixtures and temperatures have been determined. The hydrolysis half-life of the benzyl bromide with the p-hydroxy protected as the carbonate-linked alpha-methylnitroveratryl (18c) is more than 750 times that of the ether-linked analogue (16c). These studies afford a Hammett sigma(p)(+) of +0.28 for the carbonate-linked derivatives compared to a sigma(p)(+) of -0.39 for the ether-linked derivatives. The theoretical hydrolysis half-life of the most stable benzyl fluoride in 100% water was sufficiently long so as to preclude extrapolation, while the chloride was approximately 50 h, and even the bromide was estimated to be nearly 5 h.

  DOI：

  10.1021/jo991085t
• 作为产物：
  描述：

  1-(4,5-二甲氧基-2-硝基苯基)乙酮 在 sodium tetrahydroborate 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(1-bromoethyl)-4,5-dimethoxy-2-nitrobenzene
  参考文献：
  名称：

  感光性表面処理剤、積層体、トランジスタ、パターン形成方法及びトランジスタの製造方法

  摘要：

  提供一种光敏表面处理剂、一种层压板、一种晶体管、一种图案化方法和一种制造晶体管的方法。解决方案：一种光敏表面处理剂，含有由式（1）表示的化合物或由式（1）衍生的聚合物化合物。［在式(1)中，R1是氢原子或碳原子数为1～5的烷基，R2和R3各自独立地是碳原子数为1～3的烷基或碳原子数为1～13的氟烷基，R4是氢原子或硝基，n1是0或1，Y是含聚合基团的基团或碳原子数为1～2的直链或支链。0 的直链或支链烷基]。 TIFF 2023027526000069.tif 52 170 [选图] 无。

  公开号：

  JP2023027526A

文献信息

• Optical Manipulation of Subcellular Protein Translocation Using a Photoactivatable Covalent Labeling System
  作者：Toshiyuki Kowada、Keisuke Arai、Akimasa Yoshimura、Toshitaka Matsui、Kazuya Kikuchi、Shin Mizukami

  DOI：10.1002/anie.202016684

  日期：2021.5.10

  tag‐fused proteins is one of the most promising methods for regulating subcellular protein translocations and protein–protein interactions. However, light‐induced covalent protein dimerization in living cells has yet to be established, despite its various advantages. Herein, we developed a photoactivatable covalent protein‐labeling technology by applying a caged ligand to the BL‐tag system, a covalent protein

  标签融合蛋白的光活化化学诱导二聚化（photo-CID）技术是调节亚细胞蛋白质易位和蛋白质-蛋白质相互作用的最有前途的方法之一。然而，尽管光诱导共价蛋白二聚化具有多种优势，但尚未在活细胞中建立。在此，我们通过将笼状配体应用于 BL-tag 系统（一种使用突变 β-内酰胺酶的共价蛋白质标记系统）开发了一种可光活化的共价蛋白质标记技术。我们进一步开发了 CBHD，一种笼状蛋白质二聚体，使用笼状 BL-tag 和 HaloTag 配体，并实现了光诱导的蛋白质从细胞质到亚细胞区域的易位。此外，这种共价光 CID 系统能够使蛋白质快速易位到激光照射的微区域。
• NIR light controlled release of caged hydrogen sulfide based on upconversion nanoparticles
  作者：Wansong Chen、Min Chen、Qiguang Zang、Liqiang Wang、Feiying Tang、Yajing Han、Cejun Yang、Liu Deng、You-Nian Liu

  DOI：10.1039/c5cc02508g

  日期：——

  The first near-infrared (NIR) light induced H2S release platform based on upconversion nanoparticles (UCNPs) was constructed. Under NIR light excitation, UCNPs can emit UV light which triggers H2S release in...

  构建了第一个基于上转换纳米粒子（UCNPs）的近红外（NIR）光诱导的H2S释放平台。在近红外光激发下，UCNPs可以发出紫外光，从而触发H2S的释放。
• Biomolecular labeling
  申请人：University of Arkansas

  公开号：US06657052B1

  公开（公告）日：2003-12-02

  A method for using an organic compound to label polynucleotides is described. The method utilizes an organic compound including an oligonucleotide, and electrophilic active site, an active complex, and a phosphate binding site. The oligonucleotide has a sequence that is complimentary to a specific region of a polynucleotide. This facilitates labeling of DNA or RNA at a specific site in its sequence. The active site consists of a stable precursor, and only becomes reactive upon activation. Leaving and protecting functional groups may be attached to the active site in order to facilitate the formation of a stable precursor and subsequent activation. The active complex may be a drug, polypeptide or a reporter molecule such as an isotope or fluorescing compound. The phosphate binding sites may be any functional group capable of forming ionic bonds with phosphate oxygens. Nucleotide labeling using this compound does not interfere with a polynucleotide sequence. The described method for utilizing this compound may be performed in situ. Latent reactivity is utilized to make the reaction chemically specific, alkylating only phosphodiester groups on the polynucleotide. A lactonization reaction traps the trialkylphosphate in a stable form.

  描述了一种使用有机化合物标记多聚核苷酸的方法。该方法利用包括寡核苷酸、亲电活性位点、活性复合物和磷酸结合位点的有机化合物。寡核苷酸具有与多聚核苷酸特定区域互补的序列。这有助于在其序列中特定位置标记DNA或RNA。活性位点由稳定的前体组成，在激活后才变得活性。为了促进稳定前体的形成和随后的激活，可以连接离去和保护性功能基团到活性位点。活性复合物可以是药物、多肽或报告分子，如同位素或荧光化合物。磷酸结合位点可以是任何能够与磷酸氧形成离子键的功能基团。使用这种化合物进行核苷酸标记不会干扰多聚核苷酸序列。描述的利用该化合物的方法可以在原位进行。潜在的反应性用于使反应在化学上具有特异性，仅烷化多聚核苷酸上的磷酸二酯基团。内酯化反应将三烷基磷酸酯固定在稳定形式中。
• Photolabile Protecting Groups for Nitroxide Spin Labels
  作者：Ibrahim Seven、Timo Weinrich、Markus Gränz、Christian Grünewald、Silke Brüß、Ivan Krstić、Thomas F. Prisner、Alexander Heckel、Michael W. Göbel

  DOI：10.1002/ejoc.201301692

  日期：2014.7

  Nitroxide spin labels can be protected by hydrogenation and alkylation with light‐sensitive groups. Such derivatives are stable under a broad range of critical conditions used in the synthesis of peptides and oligonucleotides. When attached to a nucleoside, standard phosphoramidite chemistry allowed labeling of a short model DNA and recovery of the nitroxide in good yield.

  一氧化氮自旋标记可以通过光敏基团的氢化和烷基化来保护。这样的衍生物在肽和寡核苷酸的合成中使用的广泛的关键条件下是稳定的。当连接到核苷上时，标准的亚磷酰胺化学试剂可标记出短模型DNA，并以高收率回收氮氧化物。
• One- and Two-Photon-Activated Cysteine Persulfide Donors for Biological Targeting
  作者：Amrita Chaudhuri、Yarra Venkatesh、Joyjyoti Das、Moumita Gangopadhyay、Tapas K. Maiti、N. D. Pradeep Singh

  DOI：10.1021/acs.joc.9b01224

  日期：2019.9.20

  the biologically active persulfide (N-acetyl l-cysteine persulfide, NAC-SSH) in a spatiotemporal manner. Next, we have demonstrated the detection of persulfide release both qualitatively and quantitatively using the well-known “turn on” fluorescence probe, that is, monobromobimane, and the trapping agent, that is, 2,4-dinitrofluorobenzene, respectively. Furthermore, we examined the cytotoxicity of synthesized

  在“ S-过硫化”（一种硫介导的氧化还原循环）中，过硫化物已被视为类似于H 2 S的潜在信号传导化合物。由于缺乏有效的过硫化物供体，阻碍了对这种硫介导物质的研究。在当前的这项研究中，我们基于邻硝基苄基（ONB）光触发物开发了单光子活化和二光子活化的过硫化物供体，后者释放了生物活性的过硫化物（N-乙酰基L-半胱氨酸过硫化物（NAC-SSH）的时空分布。接下来，我们已经证明了分别使用众所周知的“开启”荧光探针（即单溴二烯）和捕集剂（即2,4-二硝基氟苯）定性和定量地检测过硫化物的释放。此外，我们检查了合成的过硫化物供体对HeLa细胞的细胞毒性以及在高度氧化的细胞环境中的细胞保护能力。