N-叔丁基萘-2-甲酰胺 | 82740-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-叔丁基萘-2-甲酰胺
• 英文名称: N-(tert-butyl)-2-naphthamide
• 英文别名: N-tert-butylnaphthalene-2-carboxamide
• CAS: 82740-58-7
• 化学式: C₁₅H₁₇NO
• mdl: MFCD00751511
• 分子量: 227.306
• InChiKey: GNUOLOZPACRWMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.266
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

SDS

N-tert-butylnaphthalene-2-carboxamideMSDS英文版

反应信息

• 作为反应物：
  描述：

  N-叔丁基萘-2-甲酰胺 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以96%的产率得到萘-2-甲酰胺
  参考文献：
  名称：

  Convenient removal of N-tert-butyl from amides with scandium triflate

  摘要：

  Scandium triflate has been used as a convenient and efficient catalyst for removal of N-tert-butyl from amide groups. A variety of N-tert-butyl aryl and alkyl amides under these conditions gave the corresponding primary amide in high yields. With the use of microwave heating the deprotection reaction could be completed within I h. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.010
• 作为产物：
  描述：

  2-萘甲酰氯 在 叔丁胺 作用下， 生成 N-叔丁基萘-2-甲酰胺
  参考文献：
  名称：

  Amide therapeutics for the treatment of inflammatory bowel disease

  摘要：

  本发明揭示了使用酰胺及相关化合物治疗或预防炎症性肠病（IBD）的方法。还揭示了含有酰胺化合物的药物组成物，其对于治疗或预防IBD有用。

  公开号：

  US06271265B1

文献信息

• Experimental and Theoretical Studies on Ru(II)-Catalyzed Oxidative C–H/C–H Coupling of Phenols with Aromatic Amides Using Air as Oxidant: Scope, Synthetic Applications, and Mechanistic Insights
  作者：Luoqiang Zhang、Lei Zhu、Yuming Zhang、Yudong Yang、Yimin Wu、Weixin Ma、Yu Lan、Jingsong You

  DOI：10.1021/acscatal.8b02816

  日期：2018.9.7

  synthesis of Palomid 529, a drug in development for the treatment of glioblastoma and neovascular age-related macular degeneration. With a combination of experimental and theoretical methods, we get more insight into the essential issues of strategy determining the reaction process. The stronger coordinating ability of 2-aryloxypyridine and the less steric hindrance of amide are pivotal to the high chemoselectivity

  我们在本文中说明了借助Zn（OTf）2的Ru（II）催化的酚与（杂）芳族酰胺的氧化邻位-C-H / C-H交叉偶联的双重螯合辅助策略。，可快速组装2'-羟基联苯-2-羧酸衍生物的丰富文库。该方案具有广泛的底物范围，优异的官能团耐受性，空气作为末端氧化剂，偶联剂的摩尔比低以及按比例放大的合成。特别是，该方法可以耐受更复杂的天然产物衍生物，从而为后期功能化提供了机会。该方案还被用作简明合成Palomid 529的关键步骤，Palomod 529是一种正在开发的用于治疗胶质母细胞瘤和新血管性年龄相关性黄斑变性的药物。结合实验和理论方法，我们对决定反应过程的策略的基本问题有更多的了解。2-芳氧基吡啶的较强的配位能力和酰胺的空间位阻较小，这是交叉偶联相对于均相偶联的高化学选择性的关键。第一个C–H键活化步骤发生在酰胺底物上，随后在2-芳氧基吡啶上的C–H键活化反应参与速率确定的步骤。
• Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon
  作者：Zhiqiang Liu、Xinglu Zhang、Jianxiong Li、Feng Li、Chunju Li、Xueshun Jia、Jian Li

  DOI：10.1021/acs.orglett.6b01928

  日期：2016.8.19

  An unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst is disclosed. The experimental results and mechanistic study show that the isocyano group acts formally as an N1 synthon during the transformation, thus expanding the reactivity profile of isocyanide.

  公开了使用碘化四丁铵（TBAI）作为催化剂的异氰酸酯和甲苯衍生物的不寻常的氧化偶联反应。实验结果和机理研究表明，异氰酸酯基团在转化过程中正式作为N1合成子起作用，从而扩大了异氰酸酯的反应活性。
• Synthesis of Amides via Palladium-Catalyzed Amidation of Aryl Halides
  作者：Huanfeng Jiang、Bifu Liu、Yibiao Li、Azhong Wang、Huawen Huang

  DOI：10.1021/ol103081y

  日期：2011.3.4

  A new and efficient method for the synthesis of amides via palladium-catalyzed C−C coupling of aryl halides with isocyanides is reported, by which a series of amides were formed from readily available starting materials under mild conditions. This transformation could extend its use to the synthesis of natural products and significant pharmaceuticals.

  报道了通过钯催化的芳基卤化物与异氰酸酯的C-C偶联合成酰胺的一种新的有效方法，通过该方法在温和的条件下由易于获得的起始原料形成了一系列酰胺。这种转变可以将其用途扩展到天然产物和重要药物的合成。
• Carboxylate-Assisted Iridium-Catalyzed C−H Amination of Arenes with Biologically Relevant Alkyl Azides
  作者：Tao Zhang、Xuejiao Hu、Zhen Wang、Tiantian Yang、Hao Sun、Guigen Li、Hongjian Lu

  DOI：10.1002/chem.201504880

  日期：2016.2.24

  wide substrate scope is reported. Benzamides with electron‐donating and ‐withdrawing groups and linear, branched, and cyclic alkyl azides are all applicable. Cesium carboxylate is crucial for both reactivity and regioselectivity of the reactions. Many biologically relevant molecules, such as amino acid, peptide, steroid, sugar, and thymidine derivatives can be introduced to arenes with high yields and

  据报道，铱催化的芳烃CHH胺化具有广泛的底物范围。具有给电子和吸电子基团以及线性，支化和环状烷基叠氮化物的苯甲酰胺均适用。羧酸铯对于反应的反应性和区域选择性都至关重要。许多生物学上相关的分子，例如氨基酸，肽，类固醇，糖和胸苷衍生物，都可以高收率和100％手性保留率引入芳烃。
• Ruthenium-Catalyzed Direct CH Amidation of Arenes Including Weakly Coordinating Aromatic Ketones
  作者：Jiyu Kim、Jinwoo Kim、Sukbok Chang

  DOI：10.1002/chem.201301025

  日期：2013.6.3

  CH activation: The ruthenium‐catalyzed direct sp2 CH amidation of arenes by using sulfonyl azides as the amino source is presented (see scheme). A wide range of substrates were readily amidated including arenes bearing weakly coordinating groups. Synthetic utility of the thus obtained products was demonstrated in the preparation of biologically active heterocycles.

  Ç  ħ激活：所述的钌催化直接SP 2 ç  ħ酰胺化，通过使用叠氮化物磺酰作为氨基源被呈现（参见方案）的芳烃。各种基材容易酰胺化，包括带有弱配位基团的芳烃。由此获得的产物的合成效用在生物活性杂环的制备中得到证明。