N-1-萘-3-氧代-3-苯基丙酰胺 | 20653-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-1-萘-3-氧代-3-苯基丙酰胺
• 中文别名: N-萘-1-基-3-氧代-3-苯基丙酰胺；3-氧代-N-(1-萘基)-3-苯基-丙酰胺；N-(1-萘基)-3-氧代-3-苯基丙酰胺；N-萘-1-基-3-氧代-3-苯基-丙酰胺
• 英文名称: N-(naphthalene-1-yl)-3-oxo-3-phenylpropanamide
• 英文别名: N-(naphthalen-1-yl)-3-oxo-3-phenylpropanamide；Benzoylessigsaeure-N-(1-naphthylamid)；N-α-Naphthyl-benzoylacetamid；Benzenepropanamide, N-1-naphthalenyl-beta-oxo-；N-naphthalen-1-yl-3-oxo-3-phenylpropanamide
• CAS: 20653-04-7
• 化学式: C₁₉H₁₅NO₂
• mdl: MFCD11974641
• 分子量: 289.334
• InChiKey: VZTJKEXGPHAIKK-UHFFFAOYSA-N

物化性质

• 沸点：
  559.3±33.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-1-萘-3-氧代-3-苯基丙酰胺 在 硫酸 作用下， 以 neat (no solvent) 为溶剂， 反应 5.5h， 以87%的产率得到4-phenylbenzo[h]quinolin-2(1H)-one
  参考文献：
  名称：

  [EN] BENZO[H]QUINOLINE LIGANDS AND COMPLEXES THEREOF
  [FR] LIGANDS DE BENZO[H]QUINOLÉINE ET COMPLEXES DE CEUX-CI

  摘要：

  本发明提供了取代的三齿苯并[h]喹啉配体及其配合物。该发明还提供了配体和相应配合物的制备方法，以及使用配合物进行催化反应的过程。

  公开号：

  WO2016193761A1
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以87 %的产率得到N-1-萘-3-氧代-3-苯基丙酰胺
  参考文献：
  名称：

  NaOH 促进 α-氧乙烯酮-N,S-缩醛的水解：有效合成 β-酮酰胺

  摘要：

  通过 NaOH 促进 α-氧乙烯酮-N,S-缩醛的水解，开发了一种有效且新颖的 β-酮酰胺合成方法。研究发现，α-氧代乙烯酮-N,S-缩醛在p...

  DOI：

  10.1080/00397911.2023.2300643

文献信息

• Cooperative Heterogeneous Organocatalysis and Homogeneous Metal Catalysis for the One-Pot Regioselective Synthesis of 2-Pyridones
  作者：Christophe Allais、Olivier Baslé、Jean-Marie Grassot、Maxime Fontaine、Stéphane Anguille、Jean Rodriguez、Thierry Constantieux

  DOI：10.1002/adsc.201200367

  日期：2012.8.13

  A direct, one-pot and regioselective access to N-alkyl- and N-aryl-substituted 2-pyridones is described from readily available β-keto amides and either primary or secondary propargylic alcohols. This approach involves the combination of two different cooperative homogeneous and heterogeneous catalytic systems based on a transition metal oxide and a supported organocatalyst, respectively.

  从容易获得的β-酮酰胺和伯或仲炔丙醇描述了直接，一锅和区域选择性地获得N-烷基-和N-芳基取代的2-吡啶酮的方法。该方法涉及分别基于过渡金属氧化物和负载型有机催化剂的两种不同的协同均相和非均相催化体系的组合。
• A Facile Synthesis of 5-Phenyl-Dibenzo[<i>b</i>,<i>g</i>][1,8]Napthyridines
  作者：Natarajan Sampathkumar、Arumugam Murugesh、Subramaniam Parameswaran Rajendran

  DOI：10.1002/jhet.2256

  日期：2016.5

  The Vilsmeier Haack heterocyclization of 2‐aryl amino‐4‐phenyl quinolines quinoline yielded the hitherto unknown 5‐phenyl‐dibenzo[b,g][1,8]naphthyridines in quantitative yield. The synthesis of aryl amines was achieved by the action of anilines on 2‐chloro‐4‐phenyl quinoline, which in turn was sourced through the combes reaction of benzoyl acetanilides.

  2芳基氨基-4-苯基喹啉的Vilsmeier Haack杂环化喹啉以定量收率产生了迄今未知的5苯基二苯并[ b，g ] [1,8]萘啶。芳基胺的合成是通过苯胺在2-氯-4-苯基喹啉上的作用而实现的，苯喹啉又是通过苯甲酰乙酰苯胺的梳理反应获得的。
• Silver(<scp>i</scp>)/base-promoted propargyl alcohol-controlled regio- or stereoselective synthesis of furan-3-carboxamides and (<i>Z</i>)-enaminones
  作者：Sabera Sultana、Jae-Jin Shim、Sung Hong Kim、Yong Rok Lee

  DOI：10.1039/c8ob01791c

  日期：——

  A novel and facile regioselective synthesis of furan-3-carboxamides by a silver(I)/base-promoted reaction of propargyl alcohol with 3-oxo amides has been demonstrated. This one-pot protocol provides a rapid synthetic approach to diverse trisubstituted furan-3-carboxamides via cascade nucleophilic addition, intramolecular cyclization, elimination, and isomerization reactions. Employing a substituted

  已经证明了通过炔丙醇与3-氧代酰胺的银（I）/碱促进的反应的呋喃-3-甲酰胺的新颖且容易的区域选择性合成。这一一锅方案通过级联亲核加成，分子内环化，消除和异构化反应，为多种三取代呋喃-3-羧酰胺提供了一种快速的合成方法。通过使用取代的炔丙醇，由3-氧代酰胺经C–N键断裂，通过Ag 2 CO 3促进的反应，具有高立体选择性的（Z）-烯胺酮。
• Processes for preparing and using ruthenium and osmium complexes
  申请人：JOHNSON MATTHEY PUBLIC LIMITED COMPANY

  公开号：US10428098B2

  公开（公告）日：2019-10-01

  The present invention relates to improved processes for the preparation of ruthenium or osmium complexes comprising acetate ligands, in particular, ruthenium complexes.

  本发明涉及制备包含醋酸配体的钌或锇络合物，特别是钌络合物的改进工艺。
• Preparation of Pincer 4-Functionalized 2-Aminomethylbenzo[<i>h</i>]quinoline Ruthenium Catalysts for Ketone Reduction
  作者：Sarah Facchetti、Vaclav Jurcik、Salvatore Baldino、Steven Giboulot、Hans Günter Nedden、Antonio Zanotti-Gerosa、Andrew Blackaby、Richard Bryan、Adrian Boogaard、David B. McLaren、Eduardo Moya、Steven Reynolds、Karl S. Sandham、Paolo Martinuzzi、Walter Baratta

  DOI：10.1021/acs.organomet.5b00978

  日期：2016.1.25

  Reaction of 1-naphthylamine with ethyl benzoylacetate gives the corresponding benzoyl acetamide derivative 1, which undergoes cyclization to 4-phenylbenzo[h]quinolin-2(1H)-one (2) in the presence of H2SO4. Bromination with POBr3, followed by reaction with n-BuLi and DATE, gives 4-phenylbenzo[h]quinoline-2-carbaldehyde (4), which is converted to the corresponding oxime hydrochloride 5 with NH2OH center dot HCL. Hydrogenation of 5 catalyzed by 10% Pd/C (type 338) leads to 4-phenyl-2-aminomethylbenzo[h]quinoline hydrochloride (HCNNPh center dot HCl, 6) isolated in high yield. Similarly, the 4-methyl-2-aminomethylbenzo[h]quinoline derivative (HCNNMe center dot HCl, 12) is prepared starting from 1-naphthylamine and 2,2,6-trimethyl-4H-1,3-dioxin-4-one, following the route for 6. Reaction of RuCl2(PPh3)(3) with a diphosphine (PP), the HCl salt 6, and NEt3 in 2-propanol leads to the pincer complexes RuCl(CNNPh)(PP) (PP = Ph2P(CH2)(3)PPh2, 13; Ph2P(CH2)(4)PPh2, 14; 1,1'-bis(diphenylphosphino)ferrocene, 15). The methyl derivatives RuCl(CNNMe) (PP) (PP = Ph2P(CH2)(3)PPh2, 16; Ph2P(CH2)(4)PPh2, 17; 1,1'-bis(diphenylphosphino)ferrocene, 18) are obtained in a similar way using 12 in place of 6. Treatment of [RuCl2(p-cymene)](2) with rac-BINAP, 6, and NEt3 affords RuCl(CNNPh)(BINAP) (19), isolated as a mixture of two diastereoisomers (3:4 molar ratio). The chiral RuCl(CNNPh)[(S,R)-JOSIPHOS] (20) is obtained as a single isomer from [RuCl2(p-cymene)](2), (S,R)-JOSIPHOS, and 6. Complexes 13-20 efficiently catalyze the transfer hydrogenation of acetophenone in 2-propanol at reflux in the presence of NaOiPr (2 mol%) with S/C = 5000-20 000 and at high rate (TOF up to 6.7 X 10(3) min(-1)). With complexes 13, 15, 17, and 18 several ketones of commercial-grade purity have been reduced to alcohols, including the bulky RCO(tBu) (R = Me, Ph) substrates. With 20 acetophenone is reduced to (S)-1-phenylethanol with 85% ee. The pincer complexes 13-15 and 18 are also found highly active in the hydrogenation of ketones at 40 degrees C with an S/C = 10 000, under 5 bar of dihydrogen in methanol and in the presence of 2 mol % of a base (NaOH, KOH, NaOMe).