methyl 3-(dibromomethyl)-4-nitrobenzoate | 207862-97-3

• 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: methyl 3-(dibromomethyl)-4-nitrobenzoate
• 英文别名: 3-dibromomethyl-4-nitrobenzoic acid methyl ester
• CAS: 207862-97-3
• 化学式: C₉H₇Br₂NO₄
• 分子量: 352.967
• InChiKey: OSLBIXRXPQCHIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(dibromomethyl)-4-nitrobenzoate 在 吡啶 、 水 作用下， 反应 1.17h， 以90%的产率得到3-甲酰基-4-硝基苯甲酸甲酯
  参考文献：
  名称：

  A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

  摘要：

  Hydrolysis of geni-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.030
• 作为产物：
  描述：

  3-甲基-4-硝基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以75%的产率得到methyl 3-(dibromomethyl)-4-nitrobenzoate
  参考文献：
  名称：

  gem-Dibromomethylarenes:  A Convenient Substitute for Noncommercial Aldehydes in the Knoevenagel−Doebner Reaction for the Synthesis of α,β-Unsaturated Carboxylic Acids

  摘要：

  [Graphics]A facile synthesis of alpha,beta-unsaturated carboxylic acids from gem-dibromomethylarenes is described. gem-Dibromomethylarenes are employed for the first time in the Knoevenagel-Doebner reaction as aldehyde equivalents for the efficient synthesis of alpha,beta-unsaturated carboxylic acids.

  DOI：

  10.1021/jo701888m

文献信息

• Synthesis of a Benzene-containing C1-Phosphonate Analogue of UDP-GlcNAc for the Inhibition of<i>O</i>-GlcNAc Transferase
  作者：Jungkyun Im

  DOI：10.1002/bkcs.10609

  日期：2016.1

  I report here the design, synthesis, and biological evaluation of a new C1‐phosphonate analogue of UDP‐GlcNAc as a potential inhibitor of OGT, an enzyme responsible for O‐GlcNAc modification. The analogue was designed to mimic the transition state of the natural donor involved in the enzymatic reaction. However, the analogue showed somehow low activity as an inhibitor of OGT.

  我在这里报告了UDP-GlcNAc的新的C1-膦酸酯类似物作为OGT的潜在抑制剂的设计，合成和生物学评估，OGT是负责O -GlcNAc修饰的酶。设计类似物以模拟参与酶促反应的天然供体的过渡态。但是，该类似物作为OGT抑制剂表现出某种程度的低活性。
• Method for inhibiting the growth of mammalian cells
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0834311A1

  公开（公告）日：1998-04-08

  A method for inhibiting mammalian cell growth is disclosed. The method uses compounds known as N-acetonylarylamides. The compounds have been shown to inhibit cell mitosis and to inhibit microtubule assembly. The method may be used to treat diseases associated with rapid cell growth, particularly cancer. The compounds used in the method of the present invention may be used in combination with other therapies and may be administered by known techniques for drug administration.

  揭示了一种抑制哺乳动物细胞生长的方法。该方法使用一种称为N-乙酰基芳胺的化合物。已经证明这些化合物可以抑制细胞有丝分裂并抑制微管组装。该方法可用于治疗与快速细胞生长相关的疾病，特别是癌症。本发明方法中使用的化合物可以与其他疗法结合使用，并可以通过已知的药物给药技术进行给药。
• o-Nitrobenzyl Photolabile Protecting Groups with Red-Shifted Absorption: Syntheses and Uncaging Cross-Sections for One- and Two-Photon Excitation
  作者：Isabelle Aujard、Chouaha Benbrahim、Marine Gouget、Odile Ruel、Jean-Bernard Baudin、Pierre Neveu、Ludovic Jullien

  DOI：10.1002/chem.200501393

  日期：2006.9.6

  quantum yields of uncaging associated with cross-sections of 1-50 GM for two-photon absorption. Although the cross-sections for one- and two-photon absorption of o-nitrobenzyl photolabile protecting groups can be readily improved, we emphasize the difficulty in enlarging the corresponding action uncaging cross-sections in view of the observed trend of their quantum yield of uncaging.

  我们评估了邻硝基苄基平台，用于设计具有红移吸收的光不稳定保护基，该保护基可在单光子和双光子激发后被光解。报道了建立不同的共轭邻硝基苄基骨架以及改变苄基位置的几种合成途径。相对于参考的4,5-二甲氧基-2-硝基苄基，几种邻硝基苄基衍生物在近紫外范围内表现出大的红移单光子吸收。通过测量模型笼状醚和酯上的紫外可见吸收和稳态荧光发射，研究了单光子激发后的解笼。在整个研究过程中，笼罩的底物在光解后被干净地释放。单光子吸收后的解开量子产率在0.1-1％的范围内。我们观察到，随着邻硝基苄基保护基团最大波长吸收的增加，这些下降。一种基于荧光相关光谱法（FCS）的双光子激发后的新方法用于测量双光子激发的作用解开截面。研究的邻硝基苄基笼状荧光香豆素系列显示的值在0.1-0.01 Goeppert-Mayer（GM）范围内。这样的结果与用于双光子吸收的与1-50 GM的横截面相关的解开的低量子产率相符。尽管邻硝
• Method for controlling algae
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0880893A1

  公开（公告）日：1998-12-02

  A method for controlling algae and marine fouling organisms is described. The method employs N-acetonylbenzamides compounds provided in an effective amount to kill or inhibit the growth of the algae or fouling organisms.

  描述了一种控制藻类和海洋污垢生物的方法。该方法利用N-乙酰基苯甲酰胺化合物，以有效量提供，以杀灭或抑制藻类或污垢生物的生长。
• C1-Phostphonate Analogue of UDP-GlcNAc for Inhibition of O-GlcNAc Transferase
  申请人：SOONCHUNHYANG UNIVERSITY INDUSTRY ACADEMY COOPERATION FOUNDATION

  公开号：US20170022243A1

  公开（公告）日：2017-01-26

  A novel C1-phosphate analogue of uridine-5′-diphosphate (UDP)-GlcNAc as an effective OGT (O-linked N-acetylglucosamine (O-GlcNAc) transferase) inhibitor, and a preparation method for the same provides a compound having an OGT inhibitory effect that can be used as a useful tool in the studies on various vital phenomena in association with the protein modification by O-GlcNAc within cells and furthermore as a candidate substance in the treatment or research of diseases related to the protein modification by O-GlcNAc, such as cancers, diabetes, or degenerative neurological diseases.

  一种新的C1-磷酸尿苷二糖（UDP-GlcNAc）类似物，作为有效的OGT（O-连接N-乙酰葡萄糖胺转移酶）抑制剂，并提供其制备方法，提供了一种具有OGT抑制作用的化合物，可用作细胞内蛋白质修饰与O-GlcNAc相关的各种重要现象的研究工具，进一步作为治疗或研究与O-GlcNAc相关的蛋白质修饰所致疾病（如癌症、糖尿病或退行性神经疾病）的候选物质。