2-naphthalen-1-yl-N-phenylacetamide | 80817-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthalen-1-yl-N-phenylacetamide
• 英文别名: 2-(1-naphthyl)-N-phenylacetamide；1-naphthylacetanilide；[1]naphthyl-acetic acid anilide；[1]Naphthyl-essigsaeure-anilid；α-Naphthylessigsaeure-anilid；Naphthyl-(1)-acetanilid
• CAS: 80817-92-1
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: ZWXQQJHQVLYBOC-UHFFFAOYSA-N

物化性质

• 溶解度：
  1.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  2-naphthalen-1-yl-N-phenylacetamide 在 四氯化钛 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1-(2-anilinoethyl)naphtalene
  参考文献：
  名称：

  方便，通用地将酰胺还原为低价钛的胺

  摘要：

  AbstractLow‐valent titanium readily prepared in situ from TiCl4 and Mg powder in THF is found to be an active agent for the reduction of amides which were previously considered to be inert towards low‐valent titanium. The reaction proceeds under very mild conditions, and is applicable to all types of amides, primary, secondary and tertiary, to produce the corresponding amines in good to excellent yields. This new finding provides a practical, convenient and general method for the important transformation of amides to amines. A plausible reaction mechanism is proposed.magnified image

  DOI：

  10.1002/adsc.201300355
• 作为产物：
  描述：

  1-萘乙酸 在 氯化亚砜 、 苯 作用下， 生成 2-naphthalen-1-yl-N-phenylacetamide
  参考文献：
  名称：

  Gilman; Kirby, Journal of the American Chemical Society, 1929, vol. 51, p. 3478

  摘要：

  DOI：

文献信息

• Carboxamides as <i>N</i> -Alkylating Reagents of Secondary Amines in Indium-Catalyzed Reductive Amination with a Hydrosilane
  作者：Yohei Ogiwara、Wataru Shimoda、Keisuke Ide、Takumi Nakajima、Norio Sakai

  DOI：10.1002/ejoc.201601629

  日期：2017.5.26

  N-alkylation of amines by using secondary amides as the alkyl source was developed. A versatile type of carboxamide functioned as an N-alkylation reagent in the presence of an indium(III) catalyst and a hydrosilane to provide alkylated tertiary amines efficiently. This amide-based catalytic N-alkylation strategy is considered to be a highly useful protocol to access unsymmetrical tertiary amines.

  开发了一种以仲酰胺为烷基源催化还原N-烷基化胺的方法。在铟 (III) 催化剂和氢硅烷的存在下，一种多功能的甲酰胺可用作 N-烷基化试剂，以有效地提供烷基化叔胺。这种基于酰胺的催化 N-烷基化策略被认为是获取不对称叔胺的非常有用的方案。
• New methods and reagents in organic synthesis. 17. Trimethylsilyldiazomethane(TMSCHN2) as a stable and safe substitute for hazardous diazomethane. Its application to the arndt-eistert synthesis.
  作者：TOYOHIKO AOYAMA、TAKAYUKI SHIOIRI

  DOI：10.1248/cpb.29.3249

  日期：——

  Although diazomethane is used in the Arndt-Eistert synthesis, it is both highly toxic and also explosive, and hence should be very carefully handled. In place of this hazardous diazomethane, stable and safe trimethylsilyldiazomethane (TMSCHN2) was found to be very useful for the Arndt-Eistert synthesis. TMSCHN2 was easily acylated with a carboxylic acid chloride in tetrahydrofuran-acetonitrile, and thermal treatment of the acylated product in benzyl alcohol and 2, 4, 6-trimethylpyridine smoothly gave the benzyl ester of a homologated acid. Nucleophiles other than benzyl alcohol could also be used. TMSCHN2 may also be able to replace diazomethane in other areas of chemistry.

  尽管偶氮甲烷在阿恩特-艾斯特合成中使用，但它具有高毒性和爆炸性，因此应该非常小心地处理。为了替代这种危险的偶氮甲烷，稳定且安全的三甲基硅烷偶氮甲烷（TMSCHN₂）被发现对于阿恩特-艾斯特合成非常有用。TMSCHN₂可以在四氢呋喃-乙腈中与卤代羧酸酰氯轻松进行酰化，酰化产物在苄醇和2,4,6-三甲基吡啶中的热处理顺利得到了一种同 homologated acid 的苄酯。除了苄醇之外，其他亲核试剂也可以使用。TMSCHN₂可能还能够替代偶氮甲烷在其他化学领域的应用。
• Synthesis of Polycyclic δ-Lactams with Bridged Benzomorphan Skeleton: Selectivity and Diversity Driven by Substituents
  作者：Jacek G. Sośnicki、Tomasz J. Idzik、Aleksandra Borzyszkowska、Gabriela Maciejewska、Łukasz Struk

  DOI：10.1021/acs.joc.7b02509

  日期：2018.2.16

  An efficient synthesis of bromofunctionalized 2,6-methano- and 1,5-methano-benzomorphanones, starting from easily available 6-benzyl-3,6-dihydropyridin-2(1H)-ones, is described. Furthermore, the synthesis of bridged benzomorphanones with hitherto not known polycyclic systems containing 2- or 3-azabicyclo[4.1.0]heptane units is developed upon treatment of both 2,6- and 1,5-methanobromobenzomorphans

  描述了从容易获得的6-苄基-3,6-二氢吡啶-2-2（1 H）-开始的溴官能化的2,6-甲基-和1,5-甲基-苯并吗啡酮的有效合成。此外，通过用t - BuOK处理2，6-和1，5-甲基溴代苯并吗啡酮，开发了具有迄今未知的含有2-或3-氮杂双环[4.1.0]庚烷单元的多环系统的桥连苯并吗啡酮的合成。研究了取代基对两种转化的多样性和立体选择性的影响。
• TETRAHYDRO-NAPHTHALENE DERIVATIVES
  申请人：Tajimi Masaomi

  公开号：US20110178088A1

  公开（公告）日：2011-07-21

  This invention relates to tetrahydro-naphthalene derivatives and salts thereof which are useful as an active ingredient of pharmaceutical preparations. The tetrahydro-naphthalene derivatives of the present invention have excellent activity as VR1 antagonist and useful for the prophylaxis and treatment of diseases associated with VR1 activity, in particular for the treatment of urinary incontinence, overactive bladder, urge urinary incontinence, chronic pain, neuropathic pain, post-operative pain, rheumatoid arthritic pain, neuralgia, neuropathies, algesia, nerve injury, ischaemia, neurodegeneration, stroke, inflammatory disorders, asthma and COPD.

  本发明涉及四氢萘衍生物及其盐，其作为药物制剂的活性成分非常有用。本发明的四氢萘衍生物具有优异的VR1拮抗剂活性，可用于预防和治疗与VR1活性相关的疾病，特别是用于治疗尿失禁、过度活动的膀胱、强烈的尿失禁、慢性疼痛、神经痛、术后疼痛、类风湿关节炎疼痛、神经痛、神经病、疼痛、神经损伤、缺血、神经退行性疾病、中风、炎症性疾病、哮喘和COPD。
• Lanthanide-catalyzed deamidative cyclization of secondary amides and ynones through tandem C–H and C–N activation
  作者：Junxi Zhang、Yitu Wang、Xigeng Zhou

  DOI：10.1039/d3cc00216k

  日期：——

  We report a new cyclization reaction of amides with ynones via tandem amide α-C–H and C–N activation enabled by a non-redox rare earth catalyst.

  我们报道了一种新的环化反应，使用非氧化还原罕见土壤金属催化剂，通过串联酰胺α-C-H和C-N活化，使酰胺与炔酮发生环化反应。