苯,1-(1-重氮基乙基)-2-硝基- | 114119-94-7

• 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: 苯,1-(1-重氮基乙基)-2-硝基-
• 英文名称: 1-(2-nitrophenyl)diazoethane
• 英文别名: 1-[(1E)-1-diazoethyl]-2-nitrobenzene
• CAS: 114119-94-7
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: ZBNVNNVXWPVJLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯,1-(1-重氮基乙基)-2-硝基- 在 dirhodium tetraacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-(2-亚硝基苯基)-乙酮
  参考文献：
  名称：

  Site-specific labelling of caged atp with deuterium or 18oxygen

  摘要：

  [3-D]2-硝基乙酰苯和[醇-18O]-1-(2-硝基苯基)乙醇被制备并用于合成带有标记的P3-L-(2-硝基苯基)乙酯的ATP（“笼型ATP”），其中同位素以氘的形式存在于硝基取代环的3-位上，或以18氧的形式存在于末端磷酸与硝基苯乙基团之间的桥接位置。氘代化合物的可用性使得其1H NMR光谱得以完全指认。

  DOI：

  10.1002/jlcr.2580360312
• 作为产物：
  描述：

  邻硝基苯乙酮 在 manganese(IV) oxide 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 3.08h， 生成 苯,1-(1-重氮基乙基)-2-硝基-
  参考文献：
  名称：

  Photolabile 1-(2-nitrophenyl)ethyl phosphate esters of adenine nucleotide analogs. Synthesis and mechanism of photolysis

  摘要：

  DOI：

  10.1021/ja00229a036

文献信息

• Syntheses of Phospholipids Containing 2-Nitrobenzyl Ester Moieties at the Terminals of Alkyl Chains and Properties of Photodegradable Liposomes from the Lipids
  作者：Kazuo Yamaguchi、Yoshihiro Tsuda、Taka-aki Shimakage、Akihiro Kusumi

  DOI：10.1246/bcsj.71.1923

  日期：1998.8

  Phospholipid 1a bearing 2-nitrobenzyl ester moieties as a photocleavable group at the terminal of alkyl chains was synthesized from the corresponding terminal carboxy-bearing phospholipid 2 by the reaction with 2-nitrophenyl-substituted diazomethane. Phospholipid, 1b bearing α-methyl-2-nitrobenzyl group, 1c bearing 4,5-dimethoxy-2-nitrobenzyl group, and 1d bearing α-methyl-4,5-dimethoxy-2-nitrobenzyl group were similarly synthesized by the use of the respective diazo compounds. The order of photolysis rates of 2-nitrobenzyl ester linkage of phospholipids by ultrahigh-pressure mercury lamp is 1b ≥ 1d > 1a > 1c. Liposomes of 1a—1d containing calcein in the inner aqueous layer were prepared by vortexing, sonication, and gel-filtration. UV irradiation resulted in fast release of the entrapped fluorescence dye. The order of release rates : 1b ≥ 1d > 1c > 1a is consistent with that of photolysis rates except for 1c, which has poor retention of the dye.

  合成了具有2-硝基苯甲酯基团的磷脂1a，该基团作为光分解基团位于烷基链的末端，通过与2-硝基苯基取代的叠氮甲烷反应，从对应的末端羧基含量磷脂2合成。磷脂1b（具有α-甲基-2-硝基苯甲基基团）、1c（具有4,5-二甲氧基-2-硝基苯甲基基团）和1d（具有α-甲基-4,5-二甲氧基-2-硝基苯甲基基团）也同样通过相应的叠氮化合物合成。通过超高压汞灯光分解的磷脂中2-硝基苯甲酯键的光解速率顺序为1b ≥ 1d > 1a > 1c。通过涡旋、超声波和凝胶过滤法制备了含有钙黄绿素的磷脂1a—1d的内水相的脂质体。紫外照射导致被捕获的荧光染料快速释放。释放速率的顺序为：1b ≥ 1d > 1c > 1a，这与光解速率的顺序一致，除了1c，其染料的保持效果较差。
• [EN] PROCESSES FOR PREPARING FUNCTIONALIZED CYCLOOCTENES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE CYCLOOCTÈNES FONCTIONNALISÉS
  申请人：TAMBO INC

  公开号：WO2020077140A1

  公开（公告）日：2020-04-16

  The present disclosure relates to processes for preparing functionalized cyclooctenes and the synthetic intermediates prepared thereby.

  本公开涉及制备功能化环辛烯及其合成中间体的工艺。
• Photoregulation of Cytochrome P450 Activity by Using Caged Compound
  作者：Kenichi Morigaki、Kazuyuki Mizutani、Emi Kanemura、Yoshiro Tatsu、Noboru Yumoto、Hiromasa Imaishi

  DOI：10.1021/ac202189h

  日期：2012.1.3

  Cytochrome P450 (P450) species play an important role in the metabolism of xenobiotics, and assaying the activities of P450 is important for evaluating the toxicity of chemicals in drugs and food. However, the lag time caused by the introduction and mixing of sample solutions can become sources of error as the throughput is heightened by increasing the sample number and decreasing the sample volume. To amend this technological obstacle, we developed a methodology to photoregulate the activity of P450 by using photoprotected (caged) compounds. We synthesized caged molecules of nicotinamide adenine dinucleotide phosphate (NADP+) and glucose 6-phosphate (G6P), which are involved in the generation of NADPH (cofactor of P450). The use of caged-G6P completely blocked the P450 catalysis before the UV illumination, whereas caged-NADP+ resulted in a little background reaction. Upon UV illumination, more than 90% of the enzymatic activity could be restored. The use of caged-G6P enabled assays in isolated microchambers (width, 50 μm; height, 50 μm) by encapsulating necessary ingredients in advance and initiating the reaction by UV illumination. The initiation of enzymatic reaction could be observed in a single microchamber. Minimizing uncertainties caused by the introduction and mixing of solutions led to significantly reduced errors of obtained kinetic constants.

  细胞色素 P450（P450）物种在异种生物的代谢过程中发挥着重要作用，而检测 P450 的活性对于评估药物和食品中化学物质的毒性非常重要。然而，随着样品数量的增加和样品量的减少，样品溶液的引入和混合所造成的滞后时间会成为误差的来源。为了克服这一技术障碍，我们开发了一种使用光保护（笼状）化合物对 P450 的活性进行光调节的方法。我们合成了烟酰胺腺嘌呤二核苷酸磷酸（NADP+）和 6-磷酸葡萄糖（G6P）的笼状分子，它们参与生成 NADPH（P450 的辅助因子）。在紫外线照射前，使用笼装 G6P 可完全阻断 P450 的催化反应，而笼装 NADP+ 则会导致少量的背景反应。紫外线照射后，90% 以上的酶活性得以恢复。使用笼式-G6P 可以在隔离的微室（宽 50 μm；高 50 μm）中进行测定，方法是提前封装必要的成分，并通过紫外线照射启动反应。在一个微室中就能观察到酶反应的起始过程。尽量减少溶液的引入和混合所造成的不确定性，大大降低了所得动力学常数的误差。
• More stable analog of isopropylthiogalactoside for induction of protein expression
  申请人：IOWA STATE UNIVERSITY RESEARCH FOUNDATION

  公开号：US20040224390A1

  公开（公告）日：2004-11-11

  A novel C-glycoside of isopropylthiogalactoside (IPTG), isobutyl-C-galactoside (IBCG), is described. IBCG may be used as an IPTG substitute for increased induction of protein expression of plasmid-based genes for the production of recombinant proteins under the control of the lac promoter. IBCG offers the advantage over IPTG of being stable at ambient temperature.

  本文描述了一种新型的异丙硫代半乳糖苷C-糖苷化物（IPTG），即异丁基-C-半乳糖苷（IBCG）。IBCG可用作IPTG替代物，用于在lac启动子控制下，增加质粒基因的蛋白表达，以生产重组蛋白。IBCG相比IPTG具有环境温度下稳定的优点。
• Photo-labile protecting agents and method
  申请人：MEDICAL RESEARCH COUNCIL

  公开号：EP0233403A1

  公开（公告）日：1987-08-26

  The invention provides diazo compounds having the formula XYCNN and their parent hydrazones, where X is an ortho-nitro aromatic group such as o-nitrophenyl and Y is a hydrocarbon group such as methyl. The hydrazones may be prepared by reacting the corresponding ketone with hydrazine and the diazo compounds by hydrazone oxidation. The diazo compound may be reacted with an organic compound having a reactive hydrogen atom such as phosphate, thiophosphate, phosphonate, carboxyl and phenol, to form a caged compound from which the original organic compound can be released by photolysis, eg in situ in a biological system. Preferred organic compounds are ATP and other nucleotides.

  本发明提供了具有式 XYCNN 的重氮化合物及其母体肼酮，其中 X 为邻硝基苯基等正硝基芳香基团，Y 为甲基等烃基团。肼酮可通过相应的酮与肼反应制备，重氮化合物可通过腙氧化反应制备。重氮化合物可与具有活性氢原子（如磷酸盐、硫代磷酸盐、膦酸盐、羧基和苯酚）的有机化合物反应，形成笼状化合物，原有机化合物可通过光解（如在生物系统中的原位光解）从中释放出来。首选的有机化合物是 ATP 和其他核苷酸。