1-(4,5-dimethoxy-2-nitrophenyl)diazoethane | 116271-29-5

• 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-(4,5-dimethoxy-2-nitrophenyl)diazoethane
• 英文别名: 1-[(1E)-1-diazoethyl]-4,5-dimethoxy-2-nitrobenzene
• CAS: 116271-29-5
• 化学式: C₁₀H₁₁N₃O₄
• 分子量: 237.215
• InChiKey: YGTNHTPZQUQMKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4,5-dimethoxy-2-nitrophenyl)diazoethane 在 三氟乙酸 作用下， 以 苯 为溶剂， 生成 (2S,3S)-2-Amino-3-benzyloxy-succinic acid 1-[1-(4,5-dimethoxy-2-nitro-phenyl)-ethyl] ester
  参考文献：
  名称：

  Synthesis and photoreactivity of caged blockers for glutamate transporters

  摘要：

  L-TBOA (L-threo-p-benzyloxyaspartate) is, so far, the most potent non-trans portable blocker for glutamate transporters. We synthesized alpha-CMCM-L-TBOA (1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. alpha-CMCM-L-TBOA (1a) is biologically inactive until UV irradiation and the photolysis of la immediately released L-TBOA to show glutamate uptake inhibition. The photoreactivity of the coumarin-type caging group was superior to that of the o-nitrobenzyl-type caging group. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01042-9
• 作为产物：
  描述：

  1-(4,5-二甲氧基-2-硝基苯基)乙酮 在 manganese(IV) oxide 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.08h， 生成 1-(4,5-dimethoxy-2-nitrophenyl)diazoethane
  参考文献：
  名称：

  Syntheses of Phospholipids Containing 2-Nitrobenzyl Ester Moieties at the Terminals of Alkyl Chains and Properties of Photodegradable Liposomes from the Lipids

  摘要：

  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。

  DOI：

  10.1246/bcsj.71.1923

文献信息

• Caged ligands and uses thereof
  申请人：Lawrence S. David

  公开号：US20060240088A1

  公开（公告）日：2006-10-26

  Provided are caged compounds comprising a ligand that specifically reacts with a receptor not naturally present in mammals. The cage is released from the ligand upon illumination of the compound with light. Also provided are cells transfected with a gene of interest and a gene encoding a receptor, the gene of interest operably linked to a genetic element capable of being induced by the receptor when bound to a ligand, and the receptor not naturally present in the species of the cell. The cells also comprise a caged ligand of the receptor. Additionally provided are methods of inducing a gene of interest in the above cells. Also provided are methods of repressing a gene of interest in a cell using caged ligands of receptors. Methods are additionally provided for inducing elimination of a target sequence in a cell of a species, using a caged ligand and a recombinase.

  提供了包含与哺乳动物中自然不存在的受体特异反应的配体的笼式化合物。当用光照射化合物时，笼子会从配体中释放出来。还提供了转染了感兴趣基因和编码受体的基因的细胞，感兴趣基因与能够被受体诱导的基因元件可操作地连接在一起，当受体与配体结合时，受体在该细胞物种中自然不存在。细胞还包括受体的笼式配体。此外，提供了在上述细胞中诱导感兴趣基因的方法。还提供了使用受体的笼式配体在细胞中抑制感兴趣基因的方法。此外，还提供了使用笼式配体和重组酶在物种的细胞中诱导靶序列的消除的方法。
• Photolytic cross-linkable monomers
  申请人：Diamond Scott

  公开号：US20060128814A1

  公开（公告）日：2006-06-15

  Photolytic cross-linkable polymers comprises three domains, a cationic domain, a cross-linkable domain and a photolabile domain. The photolytic cross-linkable polymers according to the current invention are useful in a method to complex and compact DNA and RNA for delivery to a living cell, wherein the DNA or RNA is released by photolytic degradation of a cross-linked polymer, which encapsulates the DNA or RNA in a nanoparticle.

  光解交联聚合物包括三个领域，即阳离子领域、可交联领域和光敏领域。根据当前发明，这种光解交联聚合物在将DNA和RNA复杂化并紧凑地传递到活细胞的方法中很有用，其中DNA或RNA通过交联聚合物的光解降解释放，该交联聚合物将DNA或RNA封装在纳米粒子中。
• Caged tetracycline (derivatives), their generation, and their use for photoactivated gene expression
  申请人：Cambridge Sidney

  公开号：US20060105458A1

  公开（公告）日：2006-05-18

  Transcriptionally inactivated (caged) tetracycline or tetracycline derivative, wherein the inactivation is caused by reaction of the tetracycline (derivative) with a photosensitive protection compound, said caged tetracycline or tetracycline derivative being capable to be activated again by photolysis.

  转录失活（caged）四环素或四环素衍生物，其中失活是由四环素（衍生物）与光敏保护化合物反应引起的，所述caged四环素或四环素衍生物能够通过光解再次被激活。
• 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。