N-(p-tolyl)-2-naphthamide | 67363-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(p-tolyl)-2-naphthamide
• 英文别名: N-(4-methylphenyl)naphthalene-2-carboxamide
• CAS: 67363-82-0
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: DWNGFVYSFJNAAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-萘甲腈 在 五氯化磷 、 potassium carbonate 、 苯 作用下， 生成 N-(p-tolyl)-2-naphthamide
  参考文献：
  名称：

  Vieth, Justus Liebigs Annalen der Chemie, 1876, vol. 180, p. 305

  摘要：

  DOI：

文献信息

• Catalyst-Free Singlet Oxygen-Promoted Decarboxylative Amidation of α-Keto Acids with Free Amines
  作者：Wen-Tao Xu、Bei Huang、Jian-Jun Dai、Jun Xu、Hua-Jian Xu

  DOI：10.1021/acs.orglett.6b01296

  日期：2016.7.1

  catalyst-free decarboxylative amidation of α-keto acids with amines under mild conditions has been developed. Advantages of the new protocol include avoidance of metal catalysts and high levels of functional group tolerance. In addition, the reaction can be scaled up and shows high chemoselectivity. Preliminary mechanistic studies suggest that singlet oxygen, generated from oxygen under irradiation, is the key

  已经开发了在温和条件下用胺进行的新型无催化剂的α-酮酸与胺的脱羧酰胺化反应。新协议的优点包括避免了金属催化剂和高水平的官能团耐受性。另外，该反应可以扩大规模并且显示出高的化学选择性。初步的机理研究表明，辐照下由氧气产生的单线态氧是这种无催化剂转化的关键促进剂。
• Silver-promoted decarboxylative amidation of α-keto acids with amines
  作者：Xiao-Lan Xu、Wen-Tao Xu、Ji-Wei Wu、Jian-Bo He、Hua-Jian Xu

  DOI：10.1039/c6ob01963c

  日期：——

  A general and effective method for the synthesis of amides through decarboxylative amidation of α-keto acids with amines has been developed. The reaction proceeded smoothly to afford the corresponding amide products in good yield under air and shows excellent functional group tolerance. In addition, the protocol can be further applied in the synthesis of heterocyclic compounds like benzimidazoles.

  已经开发了通过α-酮酸与胺的脱羧酰胺化来合成酰胺的通用且有效的方法。反应在空气中顺利进行，以高收率得到相应的酰胺产物，并显示出优异的官能团耐受性。另外，该方案可进一步应用于杂环化合物如苯并咪唑的合成。
• One-pot mechanosynthesis of aromatic amides and dipeptides from carboxylic acids and amines
  作者：Vjekoslav Štrukil、Boris Bartolec、Tomislav Portada、Ivica Đilović、Ivan Halasz、Davor Margetić

  DOI：10.1039/c2cc36613d

  日期：——

  Environmentally friendly one-pot synthesis of amides, bis-amides and dipeptides by mechanochemical carbodiimide-mediated coupling of carboxylic acids and amines is described; high reaction yields and simple aqueous work-up allow for the clean, practical and fast preparation of a variety of compounds containing the amide bond from readily accessible reagents.

  通过机械化学碳二亚胺介导的羧酸和胺的偶联，描述了环境友好的一锅合成酰胺，双酰胺和二肽。高反应产率和简单的水后处理使得可以从容易获得的试剂中清洁，实用，快速地制备各种含有酰胺键的化合物。
• Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O₂
  作者：Jie Liu、Qiang Liu、Hong Yi、Chu Qin、Ruopeng Bai、Xiaotian Qi、Yu Lan、Aiwen Lei

  DOI：10.1002/anie.201308614

  日期：2014.1.7

  visible‐light photoredox catalysis and radical reactions. A novel, simple, and efficient radical oxidative decarboxylative coupling with the assistant of the photocatalyst [Ru(phen)3]Cl2 is described. Various functional groups are well‐tolerated in this reaction and thus provides a new approach to developing advanced methods for aerobic oxidative decarboxylation. The preliminary mechanistic studies revealed

  光化学开创了化学发展的新纪元，光氧化还原催化已经成为一个热门话题，特别是在过去的五年中，结合了可见光光氧化还原催化和自由基反应。描述了一种新颖，简单，有效的与光催化剂[Ru（phen）3 ] Cl 2辅助的自由基氧化脱羧偶联。该反应中的各种官能团均具有良好的耐受性，因此为开发高级方法进行好氧氧化脱羧提供了一种新方法。初步的机理研究表明：1）[Ru（phen）3 ] 2+ *与苯胺之间的SET过程起重要作用；2）2激活可能是决定速率的步骤；3）脱羧步骤是不可逆且快速的过程。
• Nickel-catalyzed coupling of isocyanates with 1,3-iodoesters and halobenzenes: a novel method for the synthesis of imide and amide derivatives
  作者：Jen-Chieh Hsieh、Chien-Hong Cheng

  DOI：10.1039/b506903c

  日期：——

  Substituted imide and amide derivatives were conveniently prepared from the reaction of isocyanates with o-iodobenzoates and haloarenes catalyzed by the NiBr2(dppe)/dppe/Zn system in moderate to good yields with excellent tolerance of functional groups.

  通过异氰酸酯与邻碘苯甲酸酯和卤代芳烃的反应，采用NiBr2(dppe)/dppe/Zn体系催化，便捷地合成了取代的酰亚胺和酰胺衍生物，产率中等至良好，并且对功能团具有极好的耐受性。