N-allyl-1-naphthamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-allyl-1-naphthamide
• 英文别名: N-allyl-[1]naphthamide；N-Allyl-[1]naphthamid；1-Naphthamide, N-allyl-；N-prop-2-enylnaphthalene-1-carboxamide
• 化学式: C₁₄H₁₃NO
• mdl: MFCD03394402
• 分子量: 211.263
• InChiKey: MNDXIAYSFXOWKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-1-naphthamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以53%的产率得到5-(bromomethyl)-2-(naphthalen-2-yl)oxazole
  参考文献：
  名称：

  Catalyst-Free Intramolecular Oxidative Cyclization of N-Allylbenzamides: A New Route to 2,5-Substituted Oxazoles

  摘要：

  A catalyst-free intramolecular oxidative cyclization reaction of N-allylbenzamides has been developed to prepare 2,5-disubstituted oxazoles with good yields. This reaction gives an efficient synthetic strategy to form an oxazole nucleus directly from easily accessible substrates under temperate conditions.

  DOI：

  10.1021/ol302031z
• 作为产物：
  描述：

  1-萘甲酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-allyl-1-naphthamide
  参考文献：
  名称：

  Pd(II)-Catalyzed, Picolinamide-Assisted, Z-Selective γ-Arylation of Allylamines To Construct Z-Cinnamylamines

  摘要：

  Investigations of Pd(II)-catalyzed, picolinamide-assisted, gamma-C(sp(2))-H activation and Z-selective arylation of allylamines are reported. The reactions of N-allylpicolinamides with various aryl iodides in the presence of the catalyst Pd(OAc)(2) and additive AgOAc have led to the selective gamma-arylation of allylamines to construct various cinnamylamines with moderate to good yields and good to high E/Z ratios. To obtain good E/Z ratios, the Pd(II)-catalyzed arylation reaction of N-allylpicolinamides was probed using different additives, directing groups, and reaction conditions. The Pd(II)-catalyzed arylation of an allylamine containing both gamma-C(sp(2))-(H) and gamma-C(sp(3)) H bonds afforded moderate yields of the gamma-C(sp(2)) H and gamma-C(sp3) H bisarylated cinnamylamines. Although Heck-type gamma-arylations of allylamines have generally afforded the E-cinnamylamines, the bidentate directing group picolinamide-directed arylations of allylamines were found to be Z-selective. A plausible mechanism was proposed for the observed regioselectivity and Z-selective arylation of N-allylpicolinamides. Additionally, the Pd(II)-catalyzed arylation of an N-allyl-5-methylisoxazole-3-carboxamide afforded the E-cinnarnylamines plausibly via a ligand-free Heck-type reaction mechanism.

  DOI：

  10.1021/acs.joc.7b00535

文献信息

• Metal-Free Oxidative Functionalization of C(sp³)–H Bond Adjacent to Oxygen and Radical Addition to Olefins
  作者：Wei Zhou、Ping Qian、Jincan Zhao、Hong Fang、Jianlin Han、Yi Pan

  DOI：10.1021/acs.orglett.5b00088

  日期：2015.3.6

  A DTBP-promoted oxidative functionalization of a C(sp3)–H bond adjacent to oxygen and intermolecular radical addition to olefins without use of any metal catalyst or photoredox catalysis is reported. The reaction has a wide scope of olefin, alcohol, and cycloether substrates, which provides an easy way for direct preparation of α,ω-amino alcohols.

  据报道，在不使用任何金属催化剂或光氧化还原催化的情况下，DTBP促进了与氧相邻的C（sp 3）-H键的氧化功能化以及将分子间自由基加成至烯烃。该反应具有广泛的烯烃，醇和环醚底物范围，这为直接制备α，ω-氨基醇提供了简便的方法。
• Mercurial Diuretics. II. Methoxymercuration of N-Allyl Amides
  作者：R. L. Rowland、Wendell L. Perry、Samuel Gerstein

  DOI：10.1021/ja01145a033

  日期：1951.1
• Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides
  作者：Qing-Bao Zhang、Pan-Feng Yuan、Liang-Lin Kai、Kai Liu、Yong-Liang Ban、Xue-Yang Wang、Li-Zhu Wu、Qiang Liu

  DOI：10.1021/acs.orglett.8b03738

  日期：2019.2.15

  The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group tolerance, atom economy, and high sustainability, since ambient air and visible light are adequate for the clean construction of five- and six membered heterocycles in yields of up to 98%.
• Pd(II)-Catalyzed, Picolinamide-Assisted, <i>Z</i>-Selective γ-Arylation of Allylamines To Construct <i>Z</i>-Cinnamylamines
  作者：Ramarao Parella、Srinivasarao Arulananda Babu

  DOI：10.1021/acs.joc.7b00535

  日期：2017.7.7

  Investigations of Pd(II)-catalyzed, picolinamide-assisted, gamma-C(sp(2))-H activation and Z-selective arylation of allylamines are reported. The reactions of N-allylpicolinamides with various aryl iodides in the presence of the catalyst Pd(OAc)(2) and additive AgOAc have led to the selective gamma-arylation of allylamines to construct various cinnamylamines with moderate to good yields and good to high E/Z ratios. To obtain good E/Z ratios, the Pd(II)-catalyzed arylation reaction of N-allylpicolinamides was probed using different additives, directing groups, and reaction conditions. The Pd(II)-catalyzed arylation of an allylamine containing both gamma-C(sp(2))-(H) and gamma-C(sp(3)) H bonds afforded moderate yields of the gamma-C(sp(2)) H and gamma-C(sp3) H bisarylated cinnamylamines. Although Heck-type gamma-arylations of allylamines have generally afforded the E-cinnamylamines, the bidentate directing group picolinamide-directed arylations of allylamines were found to be Z-selective. A plausible mechanism was proposed for the observed regioselectivity and Z-selective arylation of N-allylpicolinamides. Additionally, the Pd(II)-catalyzed arylation of an N-allyl-5-methylisoxazole-3-carboxamide afforded the E-cinnarnylamines plausibly via a ligand-free Heck-type reaction mechanism.
• Catalyst-Free Intramolecular Oxidative Cyclization of <i>N</i>-Allylbenzamides: A New Route to 2,5-Substituted Oxazoles
  作者：Wei Zhou、Chen Xie、Jianlin Han、Yi Pan

  DOI：10.1021/ol302031z

  日期：2012.9.21

  A catalyst-free intramolecular oxidative cyclization reaction of N-allylbenzamides has been developed to prepare 2,5-disubstituted oxazoles with good yields. This reaction gives an efficient synthetic strategy to form an oxazole nucleus directly from easily accessible substrates under temperate conditions.