N,N-二乙基苯甲酰胺-4-羧醛 | 58287-77-7

• 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: N,N-二乙基苯甲酰胺-4-羧醛
• 英文名称: N,N-diethyl-4-formylbenzamide
• 英文别名: 4-formyl-N,N-diethylbenzamide；N,N-diethylbenzamide-4-carboxaldehyde
• CAS: 58287-77-7
• 化学式: C₁₂H₁₅NO₂
• mdl: MFCD16306014
• 分子量: 205.257
• InChiKey: OTGRTWQLBHAZFG-UHFFFAOYSA-N

物化性质

• 沸点：
  368.2±25.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二乙基苯甲酰胺-4-羧醛 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 生成 (+)-4-[(ΑR)-Α-((2S,5R)-4-烯丙基-2,5-二甲基-1-哌嗪基)-3-甲氧基苄基]-N,N-二乙基苯酰胺
  参考文献：
  名称：

  Probes for Narcotic Receptor-Mediated Phenomena. 27. Synthesis and Pharmacological Evaluation of Selective δ-Opioid Receptor Agonists from 4-[(αR)-α-(2S,5R)-4-Substituted-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]- N,N-diethylbenzamides and Their Enantiomers

  摘要：

  Potent, selective, and efficacious delta-opioid receptor agonists such as (+)-4-[(alpha R)-alpha-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide [SNC80, (+)-2] have been found to be useful tools for exploring the structural requirements which are necessary for ligands which interact with the delta-receptor. To determine the necessity for the 4-allyl moiety in (+)-2, this substituent was replaced with a variety of 4-alkyl, 4-arylalkyl, and 4-alkenyl substituents. The corresponding enantiomers of these compounds were also synthesized. The binding affinities for the mu-, delta-, and kappa-opioid receptors and efficacies in the functional GTP gamma S binding assay were determined for the (+)-2 related compounds and their enantiomers. The 4-crotyl analogue was found to have similar delta-receptor affinity and efficacy as (+)-2, but the 4-cyclopropylmethyl analogue, in the functional assay, appeared to be a partial agonist with little antagonist activity.

  DOI：

  10.1021/jm0001222
• 作为产物：
  描述：

  对醛基苯甲酸 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N,N-二乙基苯甲酰胺-4-羧醛
  参考文献：
  名称：

  二芳基甲胺的不对称合成：选择性阿片类δ受体配体的制备

  摘要：

  两种不同的方法用于构建旋光性二芳基甲胺。非对映选择性上烷基化的醛亚胺/恶唑烷2A / 2B从（派生- [R）/（小号）-phenylglycinol或对映选择性还原的4- [η 6使用手性oxazoborolidine随后胺引入，得到光学活性diarylmethylamines -铬tricarbonylbenzoyl]溴苯。

  DOI：

  10.1016/s0957-4166(98)00419-4

文献信息

• Chemoselective Schmidt Reaction Mediated by Triflic Acid: Selective Synthesis of Nitriles from Aldehydes
  作者：Balaji V. Rokade、Kandikere Ramaiah Prabhu

  DOI：10.1021/jo3008258

  日期：2012.6.15

  An excellent utility of Schmidt reaction of aldehydes to access corresponding nitriles in an instantaneous reaction is demonstrated. The reaction of aldehydes with NaN3 and TfOH furnishes the corresponding nitriles in near quantitative yields and tolerates a variety of electron-withdrawing and electron-donating substituents on the substrates. Formanilides, a common side product in Schmidt reaction

  已证明醛的Schmidt反应在瞬时反应中能很好地利用相应的腈。醛与NaN 3和TfOH的反应以接近定量的产率提供了相应的腈，并且可以承受底物上的各种吸电子和供电子取代基。在施密特反应中常见的副产物甲虫胺未在该反应中观察到。除了这些优点之外，该反应的显着特征是它显示出显着的化学选择性，因为在反应条件下对酸和酮的官能度具有很好的耐受性。该反应易于扩展，高收率并且几乎是瞬时的。
• Method of treating sexual dysfunctions with delta opioid receptor agonist compounds
  申请人：——

  公开号：US20030186872A1

  公开（公告）日：2003-10-02

  Compositions and methods for treatment of sexual dysfunctions by administering to a subject a pharmaceutical composition comprising a delta opioid receptor agonist in an amount effective to delay the onset of ejaculation in the subject during sexual stimulation.

  通过向受试者施用含有δ阿片受体激动剂的药物组合物，以延迟受试者在性刺激过程中射精的发生，用于治疗性功能障碍的组合物和治疗方法。
• A novel oxidative transformation of alcohols to nitriles: an efficient utility of azides as a nitrogen source
  作者：Balaji V. Rokade、Sanjeev K. Malekar、Kandikere Ramaiah Prabhu

  DOI：10.1039/c2cc31256e

  日期：——

  An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN3 as a source of nitrogen in the presence of a catalytic amount of Cu(ClO4)2·6H2O.

  已开发出一种高效的方法论，能够将苄醇和肉桂醇氧化为其相应的腈类化合物，并获得极佳的产率。该方法论采用DDQ作为氧化剂，TMSN3作为氮源，在微量Cu(ClO4)2·6H2O催化剂存在下进行反应。
• Controlled and Chemoselective Reduction of Secondary Amides
  作者：Guillaume Pelletier、William S. Bechara、André B. Charette

  DOI：10.1021/ja105194s

  日期：2010.9.22

  presence of 2-fluoropyridine. The electrophilic activated amide can then be reduced to the corresponding iminium using triethylsilane, a cheap, rather inert, and commercially available reagent. Imines can be isolated after a basic workup or readily transformed to the aldehydes following an acidic workup. The amine moiety can be accessed via a sequential reductive amination by the addition of silane and

  该通讯描述了一种不含金属的方法，该方法涉及在环境压力和温度下以良好至极好的收率将仲酰胺有效且受控地还原为亚胺、醛和胺。该方法包括在 2-氟吡啶存在下用三氟甲磺酸酐对仲酰胺进行化学选择性活化。然后可以使用三乙基硅烷（一种廉价、惰性且可商购的试剂）将亲电活化的酰胺还原为相应的亚胺鎓。亚胺可以在碱性处理后分离，也可以在酸性处理后容易地转化为醛。通过在一锅反应中加入硅烷和 Hantzsch 酯氢化物，可以通过顺序还原胺化获得胺部分。而且，
• Nickel-Catalyzed Carboalkenylation of 1,3-Dienes with Aldehydes and Alkenylzirconium Reagents: Access to Skipped Dienes
  作者：Cheng-Gang Wang、Yunxing Zhang、Simin Wang、Bin Chen、Yang Li、Hai-Liang Ni、Yuanji Gao、Ping Hu、Bi-Qin Wang、Peng Cao

  DOI：10.1021/acs.orglett.0c04059

  日期：2021.1.15

  three-component coupling reaction of aldehydes, 1,3-dienes, and alkenylzirconium reagents was realized. The ligand- and additive-free protocol afforded a convenient approach to the synthesis of skipped diene compounds bearing various functionals (e.g., hydroxyl, carbonyl, halide) and heterocyclic groups. The products were readily transformed into structurally diverse polyenes. The utility of this reaction was

  实现了区域和立体选择性镍催化的醛，1,3-二烯和烯基锆试剂的三组分偶联反应。不含配体和不含添加剂的方案为合成带有各种官能团（例如羟基，羰基，卤化物）和杂环基团的跳过的二烯化合物提供了一种简便的方法。产物容易转变成结构上不同的多烯。一锅操作和按比例放大制备也证明了该反应的实用性。