2-重氮基-1-[4-硝基苯基]-乙酮 | 4203-31-0

• 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: 2-重氮基-1-[4-硝基苯基]-乙酮
• 英文名称: 2-diazo-1-(4-nitrophenyl)ethanone
• 英文别名: 2-diazo-1-(4-nitrophenyl)ethan-1-one；Ethanone,2-diazo-(4-nitrophenyl)-
• CAS: 4203-31-0
• 化学式: C₈H₅N₃O₃
• 分子量: 191.146
• InChiKey: WGTLDEVOBZFRHV-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  2-重氮基-1-[4-硝基苯基]-乙酮 在 四丁基氟化铵 、 二甲基二环氧乙烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 nitrophenyl-DPD
  参考文献：
  名称：

  Altering the Communication Networks of Multispecies Microbial Systems Using a Diverse Toolbox of AI-2 Analogues

  摘要：

  There have been intensive efforts to find small molecule antagonists for bacterial quorum sensing (QS) mediated by the "universal" QS autoinducer, AI-2. Previous work has shown that linear and branched aryl analogues of AI-2 can selectively modulate AI-2 signaling in bacteria. Additionally, LsrK-dependent phosphorylated analogues have been implicated as the active inhibitory form against AI-2 signaling. We used these observations to synthesize an expanded and diverse array of AI-2 analogues, which included aromatic as well as cyclic C-1-alkyl analogues. Species-specific analogues that disrupted AI-2 signaling in Escherichia coli and Salmonella typhimurium were identified. Similarly, analogues that disrupted QS behaviors in Pseudomonas aeruginosa were found. Moreover, we observed a strong correlation between LsrK-dependent phosphorylation of these acyl analogues and their ability to suppress QS. Significantly, we demonstrate that these analogues can selectively antagonize QS in single bacterial strains in a physiologically relevant polymicrobial culture.

  DOI：

  10.1021/cb200524y
• 作为产物：
  描述：

  4-硝基苯甲酰甲醛一水合物 在 caesium carbonate 、 对甲苯磺酰肼 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以96%的产率得到2-重氮基-1-[4-硝基苯基]-乙酮
  参考文献：
  名称：

  One-pot synthesis of polyfunctional pyrazoles: an easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine

  摘要：

  A new and efficient method for the generation of alpha-diazoketones has been developed from arylglyoxal monohydrates and tosylhydrazine at room temperature. 1,3-Dipolar cycloaddition reactions were used to constructing polyfunctional pyrazole derivatives by the reaction of generated alpha-diazoketones in situ with electron-deficient alkenes, quinones and coumarins in one pot. The one-dimensional molecular packing of 1H-benzo[f]indazole-4,9-dione derivatives along the c direction demonstrated a helical chain formation via N-H center dot center dot center dot O hydrogen-bonding. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.044
• 作为试剂：
  描述：

  N-氰基二乙基胺 、 丁炔二酸二甲酯 在 2-重氮基-1-[4-硝基苯基]-乙酮 、 dirhodium tetraacetate 作用下， 反应 1.0h， 以12%的产率得到2-diethylamino-5-(p-nitrophenyl)oxazole
  参考文献：
  名称：

  Rh2(OAc)4催化分解腈中α-重氮羰基化合物制备酰基取代的腈叶立德

  摘要：

  在乙炔二羧酸二甲酯 (DMAD) 存在下，α-重氮羰基化合物在腈中的 Rh2(OAc)4 催化反应得到恶唑和吡咯衍生物。恶唑衍生物的形成通过酰基取代的腈叶立德中间体的 1,5-环化来解释，吡咯衍生物的形成通过相同中间体与 DMAD 的 1,3-偶极环加成来解释。酰基取代的腈叶立德与丙炔酸甲酯的环加成反应的区域化学表明，丙炔基型共振结构的贡献在酰基取代的腈叶立德反应中起重要作用。

  DOI：

  10.1246/bcsj.68.3469

文献信息

• The Acid-catalyzed Decomposition of Diazo Carbonyl Compounds. II. Synthesis of 2- or 5-Heteroatom-substituted Oxazoles
  作者：Toshikazu Ibata、Tsuyoshi Yamashita、Makoto Kashiuchi、Shyuji Nakano、Hiroyuki Nakawa

  DOI：10.1246/bcsj.57.2450

  日期：1984.9

  The BF3-catalyzed decomposition of m- and p-substituted α-diazoacetophenones in excess of methyl thiocyanate and ethyl thiocyanate gave the corresponding 2-methylthio-, and 2-ethylthio-5-aryloxazoles, respectively in good yields along with s-alkyl-n-aroylmethylthiocarbamates and α-ethoxyacetophenones. However, yields of 2-dimethylamino-5-aryloxazoles by the reaction of dimethylcyanamide with α-diazoacetophenones

  BF3 催化的 m-和 p-取代的 α-重氮苯乙酮在硫氰酸甲酯和硫氰酸乙酯过量时分解，分别得到相应的 2-甲硫基-和 2-乙硫基-5-芳基恶唑以及 s-烷基- n-芳酰基甲基硫代氨基甲酸酯和α-乙氧基苯乙酮。然而，通过二甲基氰胺与α-重氮苯乙酮反应产生的2-二甲氨基-5-芳基恶唑的产率很低。5-二甲氨基-或5-烷氧基-4-芳基-2-甲基恶唑是通过N,N-二甲基-α-(对硝基苯基)重氮乙酰胺或重氮乙酸烷基芳基酯与腈反应制备的。当使用苯基重氮乙酸乙酯或对氯苯基重氮乙酸甲酯时，烷基芳基乙醛酸的酮嗪与恶唑一起获得。
• Ketene Reactions with Tertiary Amines
  作者：Annette D. Allen、John Andraos、Thomas T. Tidwell、Sinisa Vukovic

  DOI：10.1021/jo402438w

  日期：2014.1.17

  zwitterions, and these undergo amine catalyzed dealkylation forming N,N-disubstituted amides. Reactions of N-methyldialkylamines show a strong preference for methyl group loss by displacement, as predicted by computational studies. Loss of ethyl groups in reactions with triethylamine also occur by displacement, but preferential loss of isopropyl groups in the phenylketene reaction with diisopropylethylamine

  叔胺在乙腈中与芳基烯酮快速可逆地反应，形成可观察到的两性离子，并且这些胺经历胺催化的脱烷基化反应，形成N，N-二取代的酰胺。N-甲基二烷基胺的反应显示出对取代引起的甲基损失的强烈偏好，如计算研究所预测的那样。与三乙胺反应中乙基的损失也可通过置换而发生，但苯乙烯酮与二异丙基乙胺反应中异丙基的优先损失显然涉及消除。奎尼丁与芳基乙烯酮迅速形成长寿命的两性离子，为金鸡纳和相关生物碱在乙烯酮的立体选择性加成中提供了催化模型。
• Facile and efficient preparation of α-halomethyl ketones from α-diazo ketones catalyzed by iron(III) halides and silica gel
  作者：Xinxia Shi、Lingqiong Zhang、Pengfei Yang、Han Sun、Yilan Zhang、Chunsong Xie、Zhen Ou-yang、Min Wang

  DOI：10.1016/j.tetlet.2018.02.024

  日期：2018.3

  An efficient and mild method for the synthesis of α-halomethyl ketones from α-diazo ketones was developed using ferric chloride or bromide as the halogen source and silica gel as the hydrogen source, with good to excellent yields.

  以氯化铁或溴​​化物为卤素源，硅胶为氢源，开发了一种由α-重氮酮合成α-卤代甲基酮的高效温和方法。
• Geminal bisphosphonic acids and derivatives as anti-arthritic agents
  申请人：The Upjohn Company

  公开号：US05220021A1

  公开（公告）日：1993-06-15

  Unsaturated geminal phosphonates (III) ##STR1## either as the esters, free acids or salts are useful in the treatment of arthritis.

  不饱和的磷酰亚磷酸(III)无论是作为酯、游离酸还是盐，在治疗关节炎方面都有用。
• Novel <i>N</i>-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
  作者：Guan-Han Lu、Tzu-Chia Huang、Hsiao-Chin Hsueh、Shin-Cherng Yang、Ting-Wei Cho、Ho-Hsuan Chou

  DOI：10.1039/d1cc01285a

  日期：——

  direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides from N-terminal dipeptides (32 examples, up to 91%)

  开发了一种新型通用N-转移试剂，可在温和的碱性条件下直接有效地将 α-氨基酮、乙酰胺和酯转化为相应的 α-重氮产物。这种一步合成方法不仅允许从 α-氨基酸衍生物生成 α-取代-α-重氮羰基化合物，而且允许从N-末端二肽制备 α-重氮二肽（32 个例子，高达 91%） .