1-(3-nitrophenyl)-2-(piperidin-1-yl)ethane-1,2-dione | 1415049-18-1

• 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-(3-nitrophenyl)-2-(piperidin-1-yl)ethane-1,2-dione
• 英文别名: 1-(3-Nitrophenyl)-2-piperidin-1-ylethane-1,2-dione；1-(3-nitrophenyl)-2-piperidin-1-ylethane-1,2-dione
• CAS: 1415049-18-1
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: AJMRMRYCWQAPKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-硝基苯乙烯 在 碘 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 16.5h， 生成 1-(3-nitrophenyl)-2-(piperidin-1-yl)ethane-1,2-dione
  参考文献：
  名称：

  Metal free one-pot synthesis of α-ketoamides from terminal alkenes

  摘要：

  从末端烯烃合成α-酮酰胺的实用方法已经开发出来，使用I₂/IBX在一锅反应条件下。

  DOI：

  10.1039/c5ra05671c

文献信息

• Cu(<scp>i</scp>)-Functionalized SBA-16: an efficient catalyst for the synthesis of α-ketoamides under moderate conditions
  作者：Xueyao Zhang、Honglei Yang、Yong Huo、Jing Li、Jianxin Ma、Jiantai Ma

  DOI：10.1039/c5dt04969e

  日期：——

  An efficient catalyst based on the cage-like mesoporous material SBA-16 as the support and Cu(I) as active sites has been successfully prepared. The catalyst demonstrated high catalytic activity (up to 88%) in the direct oxidative synthesis of α-ketoamides between acetophenone and piperidine, employing O2 from open air as the oxidant without other additives. A heterogeneous catalyst was applied in this reaction for the first time, and the catalyst could be easily separated from the reaction system by filtration and reused several times without a significant loss of activity.

  一种高效催化剂已成功制备，以笼状介孔材料SBA-16作为载体，以Cu(I)作为活性位点。该催化剂在乙酰苯与哌啶的直接氧化合成α-酮酰胺中表现出高催化活性（高达88%），采用开空气中的O2作为氧化剂，无需其他添加剂。这种反应首次使用了异相催化剂，催化剂可以通过过滤轻松从反应体系中分离，并在未显著失活的情况下多次重复使用。
• Metal free synthesis of α-keto amides from 2-hydroxy acetophenones through domino alcohol oxidation–oxidative amidation reaction
  作者：Surya Srinivas Kotha、Govindasamy Sekar

  DOI：10.1016/j.tetlet.2015.09.053

  日期：2015.11

  An efficient method for the synthesis of α-keto amides using 2-iodoxybenzoic acid (IBX) promoted domino alcohol oxidation and oxidative amidation reaction sequence between 2-oxoalcohols and amines under metal-free conditions is developed. In this protocol, IBX is used as an oxidizing agent to synthesize the α-keto amides, which makes this methodology highly efficient, practical, and environmentally

  开发了一种在无金属条件下利用2-碘氧基苯甲酸（IBX）促进多米诺骨牌醇氧化和2-氧代醇与胺类之间的氧化酰胺化反应顺序合成α-酮酰胺的有效方法。在该协议中，IBX用作氧化剂来合成α-酮酰胺，这使该方法高效，实用且对环境无害。
• Copper-catalyzed aerobic oxidative synthesis of α-ketoamides from methyl ketones, amines and NIS at room temperature
  作者：Juan Zhang、Ying Wei、Shaoxia Lin、Fushun Liang、Pengjun Liu

  DOI：10.1039/c2ob26586a

  日期：——

  A simple, efficient and practical copper-catalyzed aerobic oxidative synthesis of α-ketoamides from aryl methyl ketones, aliphatic amines and N-iodosuccinimide (NIS) has been developed. The one-pot reaction may proceed smoothly at room temperature in the open air. The possible mechanism for the formation of α-ketoamides was proposed. Molecular oxygen in air functions as both an oxidant and an oxygen

  由芳基甲基酮，脂肪族胺和三价胺简单，高效，实用地铜催化需氧氧化合成α-酮酰胺 N-碘琥珀酰亚胺（NIS）已开发。一锅法反应可以在室温下在露天条件下平稳进行。提出了形成α-酮酰胺的可能机理。空气中的分子氧既充当氧化剂又充当氧气源。
• Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides
  作者：Jingming Zhang、Chengkou Liu、Man Yang、Zheng Fang、Kai Guo

  DOI：10.1016/j.tetlet.2020.152555

  日期：2020.11

  A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism

  已经开发了一种新的由铜催化的氢肉桂醛的好氧氧化C（sp3）–C（sp3）键裂解合成α-酮酰胺的方法。易获得且对环境无害的氧气用作氧化剂。该反应避免使用贵金属催化剂或专门的氧化剂，并且化学选择性地产生α-酮酰胺。此外，基于各种控制实验，提出了一种合理的机制。
• Iodine–TBHP mediated efficient synthesis of α-ketoamides from vinyl azides and amines under mild conditions
  作者：Swadhapriya Bhukta、Rana Chatterjee、Rambabu Dandela

  DOI：10.1039/d2ob00458e

  日期：——

  for α-ketoamides has been developed under mild conditions. The facile synthesis of α-ketoamides has been accomplished using aryl vinyl azides and secondary amines at room temperature. The inexpensive and readily available iodine and TBHP easily promoted the oxidative amidation process to afford diketoamide derivatives in high yields. This method involves the synthesis of ketoamide compounds via sequential

  在温和条件下开发了一种方便实用的α-酮酰胺合成方法。使用芳基乙烯基叠氮化物和仲胺在室温下轻松合成了 α-酮酰胺。廉价且容易获得的碘和 TBHP 很容易促进氧化酰胺化过程，以高产率提供二酮酰胺衍生物。该方法涉及通过连续的 C-O 和 C-N 键形成合成酮酰胺化合物。此外，无金属和有氧条件以及广泛的底物范围是该协议的显着优势。