m-nitrophenylglyoxal monohydrate | 5000-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: m-nitrophenylglyoxal monohydrate
• 英文别名: 2,2-Dihydroxy-1-(3-nitrophenyl)ethanone；2,2-dihydroxy-1-(3-nitrophenyl)ethanone
• CAS: 5000-63-5
• 化学式: C₈H₇NO₅
• 分子量: 197.147
• InChiKey: HTIOVQDVWZALRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  m-nitrophenylglyoxal monohydrate 在 caesium carbonate 、 对甲苯磺酰肼 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以94%的产率得到2-diazo-1-(3-nitrophenyl)ethanone
  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
• 作为产物：
  描述：

  间硝基苯乙酮 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 m-nitrophenylglyoxal monohydrate
  参考文献：
  名称：

  生物活性化合物的加巴喷丁碱合成和理论研究：N-cyclohexyl-3-oxo-2-(3-oxo-2-azaspiro[4.5] decan-2-yl)-3-arylpropanamides 和 N-(tert-butyl) )-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)-2-芳基乙酰胺衍生物

  摘要：

  摘要 2-(1-(氨基甲基)环己基)乙酸（加巴喷丁）与乙二醛和异氰环己基或芳香醛和异氰叔丁酯在温和条件下在乙醇中进行分子间Ugi反应，制备了两类新型N-环己基- 3-(芳基)-3-氧代-2-(3-氧代-2-氮杂螺[4.5]癸烷-2-基)丙酰胺和N-(叔丁基)-2-(3-氧-2-氮杂螺[4.5] 4.5]癸烷-2-基)-2-芳基乙酰胺衍生物，产率良好至极好。这是关于加巴喷丁、乙二醛和异氰化物的分子间 Ugi 三组分反应的第一份报告。另外根据理论研究，给电子基团增加了分子内氢键的强度，吸电子基团降低了分子内氢键的强度。

  DOI：

  10.1016/j.molstruc.2017.09.061

文献信息

• Synthesis and solid-state luminescence of highly-substituted 6-amino-2H-pyran-2-one derivatives
  作者：Sergey Karpov、Yakov Kayukov、Arthur Grigor'ev、Oleg Nasakin、Olga Kayukova、Viktor Tafeenko

  DOI：10.1016/j.tetlet.2020.152084

  日期：2020.7

  A fast and convenient synthesis and solid-state luminescence properties of new highly-substituted 6-amino-2H-pyran-2-one derivatives is described. These compounds were obtained from inexpensive and available 2-acyl(aroyl)-1,3-dicyano-1,3-bis-methoxycarbonylpropenides via regioselective heterocyclization under the action of sulfuric and hydroiodic acid. Compounds containing 6-amino-2H-pyran-2-one moiety

  描述了一种新的高度取代的6-氨基-2H-吡喃-2-酮衍生物的快速，方便的合成和固态发光性能。这些化合物是在硫酸和氢碘酸的作用下，通过区域选择性杂环化从廉价且可得的2-酰基（芳酰基）-1,3-二氰基-1,3-双-甲氧基羰基丙烯化物获得的。几乎没有研究含有6-氨基-2H-吡喃-2-酮部分的化合物，但是对于基于该支架获得缩合的生物活性化合物是有意义的。
• Chemoselective synthesis of biheterocyclic skeletons tetrahydro-1H-pyrrolo[1,2-c]imidazole and tetrahydropyrrolo[1,2-c]thiazole derivatives via multicomponent self-sorting domino strategy
  作者：Qun Cai、Feng-Cheng Jia、Deng-Kui Li、Cheng Xu、Ke-Rong Ding、An-Xin Wu

  DOI：10.1016/j.tet.2015.06.104

  日期：2015.9

  A highly efficient chemoselective synthesis of multifunctionalized tetrahydro-1H-pyrrolo[1,2-c]imidazole and tetrahydropyrrolo[1,2-c]thiazole derivatives has been established from arylglyoxal monohydrates, nitriles, and thioureas. A series of control experiments suggested that this reaction proceeded through the convergent integration of two self-sorting domino sequences. This synthetic strategy is

  从芳基乙二醛一水合物，腈和硫脲建立了多官能化四氢-1 H-吡咯并[1,2- c ]咪唑和四氢吡咯并[1,2 - c ]噻唑衍生物的高效化学选择性合成。一系列对照实验表明，该反应是通过两个自排序多米诺骨牌序列的融合整合而进行的。这种合成策略有望用于生物碱类似物的多样性导向合成。
• Survey reactivity of 2-aminopyridine and Meldrum’s acid in the presence of aryl glyoxals or aryl aldehydes; ethyl 2-(3-aryl imidazo[1,2-a]pyridin-2-yl)acetates versus ethyl 3-aryl-3-(pyridin-2-ylamino)propanoates
  作者：Sara Asadi、Maedeh Zebarjad、Hamidreza Masoudi、Hossein Mehrabi

  DOI：10.1007/s11164-021-04554-z

  日期：2022.1

  survey reactivity of 2-aminopyridine and Meldrum’s acid in the presence of aryl glyoxals or aryl aldehydes. The ethyl 2-(3-aryl imidazo[1,2-a]pyridin-2-yl)acetates were successfully synthesized by reaction of 2-aminopyridine, Meldrum’s acid, and aryl glyoxals, while the ethyl 3-aryl-3-(pyridin-2-ylamino)propanoates were synthesized in the presence of aryl aldehydes. The reactions are performed in ethanol

  本研究的目的是调查 2-氨基吡啶和 Meldrum 酸在芳基乙二醛或芳基醛存在下的反应性。2-(3-芳基咪唑并[1,2 - a ]吡啶-2-基)乙酸乙酯是通过2-氨基吡啶、Meldrum酸和芳基乙二醛反应成功合成的，而3-芳基-3-(在芳基醛的存在下合成了吡啶-2-基氨基）丙酸酯。反应在乙醇中进行，在回流和微波条件下由乙酸催化。 图形摘要
• Acid-Promoted Multicomponent Tandem Cyclization to Synthesize Fully Substituted Oxazoles via Robinson–Gabriel-Type Reaction
  作者：Rong-Rong Zhou、Qun Cai、Deng-Kui Li、Shi-Yi Zhuang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.joc.7b00763

  日期：2017.6.16

  An acid-promoted multicomponent reaction for the synthesis of diverse fully substituted oxazole derivatives from simple and readily available arylglyoxal monohydrates, nitriles, and various C-nucleophiles has been developed. This protocol features wide functional group diversity which is capable of installing 4-hydroxycoumarin, 2-naphthol, and 1,3-cyclohexanedione motifs to oxazoles. Mechanistic analysis

  已经开发了一种由酸促进的多组分反应，用于从简单易得的芳基乙二醛一水合物，腈和各种C-亲核试剂中合成各种完全取代的恶唑衍生物。该协议具有广泛的官能团多样性，能够将4-羟基香豆素，2-萘酚和1,3-环己二酮基序安装到恶唑类化合物上。机理分析表明，经典的Robinson-Gabriel反应是这种串联转化的关键步骤。
• One-pot, three-component synthesis of pyranocoumarins containing an aroyl group
  作者：Saeed Khodabakhshi、Fariba Jafari、Farzaneh Marahel、Mojtaba Baghernejad

  DOI：10.1515/hc-2014-0099

  日期：2014.10.1

  An expeditious method to prepare pyranocoumarins containing an aroyl group by the three-component reaction of 4-hydroxycoumarin with arylglyoxals and malononitrile is described. The reaction is efficiently catalyzed by Mohr’s salt, and the products were obtained in good to excellent yields with high purity. The method is simple, inexpensive, and environmentally friendly.

  摘要：描述了一种快速制备含有芳酰基的吡喃香豆素的方法，通过4-羟基香豆素与芳基甘氧醛和丙二腈的三组分反应。该反应在莫尔氏盐的高效催化下进行，产物收率良好至优良，纯度高。该方法简单、廉价且环保。