4-phenylbenzo[h]quinolin-2(1H)-one | 64322-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-phenylbenzo[h]quinolin-2(1H)-one
• 英文别名: 4-Phenyl-1H-benzo[h]quinolin-2-one
• CAS: 64322-59-4
• 化学式: C₁₉H₁₃NO
• 分子量: 271.318
• InChiKey: GNARUJTZXQTRIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-phenylbenzo[h]quinolin-2(1H)-one 在 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 2-chloro-3-formyl-4-phenylbenzo[h]quinoline
  参考文献：
  名称：

  夹钳式4-官能化2-氨基甲基苯并[h]喹啉钌催化剂的制备

  摘要：

  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).

  DOI：

  10.1021/acs.organomet.5b00978
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 硫酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 9.0h， 生成 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

文献信息

• [EN] BENZO[H]QUINOLINE LIGANDS AND COMPLEXES THEREOF<br/>[FR] LIGANDS DE BENZO[H]QUINOLÉINE ET COMPLEXES DE CEUX-CI
  申请人：JOHNSON MATTHEY PLC

  公开号：WO2016193761A1

  公开（公告）日：2016-12-08

  The present invention provides substituted tridentate benzo[h]quinoline ligands and complexes thereof. The invention also provides the preparation of the ligands and the respective complexes, as well as to processes for using the complexes in catalytic reactions.

  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。
• Lactamization of sp²C−H Bonds with CO₂: Transition-Metal-Free and Redox-Neutral
  作者：Zhen Zhang、Li-Li Liao、Si-Shun Yan、Lei Wang、Yun-Qi He、Jian-Heng Ye、Jing Li、Yong-Gang Zhi、Da-Gang Yu

  DOI：10.1002/anie.201602095

  日期：2016.6.13

  The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C−H bonds to synthesize important 2‐quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition‐metal‐free and redox‐neutral process is eco‐friendly and desirable

  据报道，在烯基和杂芳基CH键的内酰胺化中首次直接使用二氧化碳以中等至极好的收率合成重要的2-喹啉酮和多杂环化合物。二氧化碳是一种无毒，廉价且易于获得的温室气体，是理想的羰基来源。重要的是，这种无过渡金属和氧化还原中性的工艺对生态友好，是制药业的理想之选。此外，这些反应具有广泛的底物范围，良好的官能团耐受性，简便的可扩展性和易于产品衍生化的特点。
• Compounds, Compositions and Methods of Inhibiting Alpha-Synuclein Toxicity
  申请人：Lindquist Susan L.

  公开号：US20080261953A1

  公开（公告）日：2008-10-23

  Compounds and compositions are provided for treatment or amelioration of one or more symptoms of α-synuclein toxicity, α-synuclein mediated diseases or diseases in which α-synuclein fibrils are a symptom or cause of the disease. In one embodiment, the compounds for use in the compositions and methods are heteroaryl acylguanidines, heteroarylhydrazones, dihy-dropyridones, heteroaryl and aryl styryl ketones, and heteroarylpyrazoles.

  提供了化合物和组合物，用于治疗或缓解α-突触核蛋白毒性、α-突触核蛋白介导的疾病或α-突触核蛋白纤维是疾病症状或病因的疾病中的一个或多个症状。在一种实施例中，用于组合物和方法的化合物是杂环基酰基胍、杂环基腙、二氢吡啶酮、杂环基和芳基苯乙酮以及杂环基吡唑。
• Compounds, compositions and methods of inhibiting alpha-synuclein toxicity
  申请人：Lindquist Susan L.

  公开号：US08440705B2

  公开（公告）日：2013-05-14

  Compounds and compositions are provided for treatment or amelioration of one or more symptoms of α-synuclein toxicity, α-synuclein mediated diseases or diseases in which α-synuclein fibrils are a symptom or cause of the disease. In one embodiment, the compounds for use in the compositions and methods are heteroaryl acylguanidines, heteroarylhydrazones, dihydropyridones, heteroaryl and aryl styryl ketones, and heteroarylpyrazoles.

  提供了化合物和组合物，用于治疗或缓解α-突触核蛋白毒性、α-突触核蛋白介导的疾病或α-突触核蛋白纤维是该疾病的症状或原因的疾病的一个或多个症状。在一种实施例中，用于组合物和方法的化合物为杂环基酰基胍、杂环基肼酮、二氢吡啶酮、杂环基和芳基苯乙酮以及杂环基吡唑。
• Compounds, compositions and methods of inhibiting a-synuclein toxicity
  申请人：The Whitehead Institute for Biomedical Research

  公开号：EP2433634A2

  公开（公告）日：2012-03-28

  Compounds and compositions are provided for treatment or amelioration of one or more symptoms of a-synuclein toxicity, a-synuclein mediated diseases or diseases in which a-synuclein fibrils are a symptom or cause of the disease. In one embodiment, the compounds for use in the compositions and methods are heteroaryl acylguanidines, heteroarylhydrazones, dihydropyridones, heteroaryl and aryl styryl ketones, and heteroarylpyrazoles.

  提供的化合物和组合物用于治疗或改善a-突触核蛋白毒性、a-突触核蛋白介导的疾病或a-突触核蛋白纤维是症状或病因的疾病的一种或多种症状。在一个实施方案中，用于组合物和方法的化合物是杂芳基酰基胍、杂芳基肼、二氢吡啶酮、杂芳基和芳基苯乙烯基酮以及杂芳基吡唑。