1-(4-甲基-1(2H)-喹啉基)乙酮 | 402822-99-5

• 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
• 中文名称: 1-(4-甲基-1(2H)-喹啉基)乙酮
• 英文名称: 1-(4-methylquinolin-1(2H)-yl)ethanone
• 英文别名: 1-acetyl-4-methyl-1,2-dihydro-quinoline；1-Acetyl-4-methyl-1,2-dihydro-chinolin；1-acetyl-4-methyl-1,2-dihydroquinoline；1-(4-methyl-2H-quinolin-1-yl)ethanone
• CAS: 402822-99-5
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: GTILEMNEKQIPMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-甲基-1(2H)-喹啉基)乙酮 在 air 、 silica gel 作用下， 以 正己烷 为溶剂， 以55.6 mg的产率得到4-甲基喹啉
  参考文献：
  名称：

  A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

  摘要：

  A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2-dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.084
• 作为产物：
  描述：

  2-异丙烯苯基苯胺 在 tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 1-(4-甲基-1(2H)-喹啉基)乙酮
  参考文献：
  名称：

  A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

  摘要：

  A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2-dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.084

文献信息

• Iridium-catalyzed selective 1,2-hydrosilylation of N-heterocycles
  作者：Jinseong Jeong、Sehoon Park、Sukbok Chang

  DOI：10.1039/c6sc01037g

  日期：——

  excellent selectivity, and good functional group tolerance. The substrate scope was highly broad, including (iso)quinolines, substituted pyridines, pyrimidines, pyrazines, deazapurines, triazines, and benzimidazoles. Mechanistic studies such as a kinetic profile, rate-order assessment, and investigation of the electronic substituent effects on the initial rates were performed to access the detailed

  发现由 [Ir(coe) 2 Cl] 2和 Et 2 SiH 2原位生成的亚甲硅基桥联 Ir 二聚体可以催化 N-杂芳烃的氢化硅烷化，提供具有高活性（高达 1000 吨）的脱芳构氮杂环产物，优异的选择性和良好的官能团耐受性。底物范围非常广泛，包括（异）喹啉、取代吡啶、嘧啶、吡嗪、氮杂嘌呤、三嗪和苯并咪唑。进行了动力学概况、速率顺序评估和电子取代基对初始速率影响的研究等机理研究，以获取详细的途径。提出了一种途径涉及 C 的分子内插入 底物的 N 部分进入静止物质的 Ir-H 键，形成 Ir-酰胺基甲硅烷基中间体，然后进行还原消除。该合成实用性已通过金鸡纳生物碱的成功应用以及 1,2-二氢喹啉产品的轻松合成后转化得到证实。
• METHOD FOR MANUFACTURING OPTICALLY ACTIVE COMPOUND
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20170022162A1

  公开（公告）日：2017-01-26

  The present invention provides a method for manufacturing an optically active compound of formula (2), which contains bringing hydrogen into contact with a compound of formula (1) in the presence of a transition metal catalyst having an optically active ligand. In the formula, R 1 represents a hydrogen atom or an acetyl group, R 2 , R 3 , R 4 , and R 5 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a nitro group, an amino group, or an acyl group, R 6 represents an alkyl group, R 7 and R 8 each independently represents a hydrogen atom or an alkyl group, and a carbon atom marked with an asterisk (*) represents an asymmetric carbon atom.

  本发明提供了一种制备式（2）的光学活性化合物的方法，其中包括在具有光学活性配体的过渡金属催化剂存在下，将氢与式（1）的化合物接触。在该式中，R1代表氢原子或乙酰基，R2、R3、R4和R5各自独立地代表氢原子、卤素原子、烷基、烷氧基、羟基、硝基、氨基或酰基，R6代表烷基，R7和R8各自独立地代表氢原子或烷基，而用星号（*）标记的碳原子代表一个不对称碳原子。
• Tetrahydroquinoline derivatives
  申请人：Timmers Marius Cornelis

  公开号：US20060142334A1

  公开（公告）日：2006-06-29

  The present invention relates to tetrahydroquinoline derivatives having gene formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1 and R 2 are H or Me; R 3 is H, hydroxy, (1-4C)alkoxy, (di)(1-4C)alkylamino(2-4C)alkoxy or (2-6)heterocycloakl(2-4C)alkoxy; R 4 is H, OH, (1-4C)alkoxy or R 7 ; R 5 is H, OH, (1-4C)alkoxy or R 7 , with the proviso that if R 4 is H, R 5 is not H, OH or (1-4C)alkoxy and that if R 5 is H, R 4 is not H, OH or (1-4C)alkoxy; R 6 is (2-5C)heteroaryl, (6C)aryl, (3-8C)cycloalkyl, (2 6C)heterocycloalkyl or (1-6C)alkyl; R 7 is amino, (di)(1-4C)alkylamino, (6C)arylcarbonylamino, (6C)arylcarbonyloxy, (2-5C) heteroarylcarbonylamino, (2-5C)heteroarylcarbonyloxy, R 8 -(2-4C)alkylamino, R 8 -(2-4C)alkoxy, R 9 -methylamino or R 9 -methoxy; R 8 is hydroxy, amino, (-14C)alkoxy, (di)(1-4C)alkylamino, (2-6C)heterocycloalkyl, (2-6C) heterocycloalkylcarbonylamino, (di)(1-4C)alkylaminocarbonylamino, (1-4C)alkoxycarbonylamino and R 9 is aminocarbonyl, (di)(1-4C)alkylaminocarbonyl, (2-5C)heteroaryl or (6C)aryl. The present invention also relates to pharmaceutical compositions comprising said derivatives and the use of these derivatives to regulate fertility.

  本发明涉及具有通式（I）或其药学上可接受的盐的四氢喹啉衍生物，其中R1和R2为H或Me；R3为H、羟基、（1-4C）烷氧基、（二）（1-4C）烷基氨基（2-4C）烷氧基或（2-6）杂环烷基（2-4C）烷氧基；R4为H、OH、（1-4C）烷氧基或R7；R5为H、OH、（1-4C）烷氧基或R7，但如果R4为H，则R5不是H、OH或（1-4C）烷氧基，如果R5为H，则R4不是H、OH或（1-4C）烷氧基；R6为（2-5C）杂环芳基、（6C）芳基、（3-8C）环烷基、（2-6C）杂环烷基或（1-6C）烷基；R7为氨基、（二）（1-4C）烷基氨基、（6C）芳基羰基氨基、（6C）芳基羰氧基、（2-5C）杂环芳基羰基氨基、（2-5C）杂环芳基羰氧基、R8-（2-4C）烷基氨基、R8-（2-4C）烷氧基、R9-甲基氨基或R9-甲氧基；R8为羟基、氨基、（-14C）烷氧基、（二）（1-4C）烷基氨基、（2-6C）杂环烷基、（2-6C）杂环烷基羰基氨基、（二）（1-4C）烷基氨基羰基氨基、（1-4C）烷氧基羰基氨基；R9为氨基羰基、（二）（1-4C）烷基氨基羰基、（2-5C）杂环芳基或（6C）芳基。本发明还涉及包含上述衍生物的制药组合物以及使用这些衍生物调节生育的方法。
• Tetrahydorquinoline derivatives and their use as fsh receptor modulators
  申请人：Timmers Marius Cornelis

  公开号：US20060167047A1

  公开（公告）日：2006-07-27

  The present invention relates to tetrahydroquinoline derivatives having general formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1 and R 2 are H, Me; R 3 is (2-6C)heterocycloalkyl(1-4C)alkyl, (2-5C)heteroaryl(1-4C)alkyl, (6C)aryl (1-4C)alkyl, (1-4C)(di)alkylaminocarbonylamino(2-4C)alkyl, (2-6C) heterocycloalkylcarbonylamino(2-4C)alkyl, R 5 -(2-4C)alkyl or R 5 -carbonyl(1-4C)alkyl; R 4 is (2-5C)heteroaryl, (6C)aryl, (3-8C)cycloalkyl, (2-6C)heterocycloalkyl or (1-6C) alkyl and R 5 is (di)(1-4C)alkylamino, (1-4C)alkoxy, amino, hydroxy, (6C)arylamino, (di)(3-4C)alkenylamino, (2-5C)heteroaryl(1-4C)alkylamino, (6C)aryl(1-4C) alkylamino, (di)[(1-4C)alkoxy(2-4C)alkyl]amino, (di)[(1-4C)alkylamino(2-4C) alkyl]amino, (di)[amino(2-4C)alkyl]amino or (di)[hydroxy(2-4C)alkyl]amino. The present invention also relates to pharmaceutical compositions comprising said derivatives and the use of these derivatives to regulate fertility.

  本发明涉及具有一般式（I）或其药学上可接受的盐的四氢喹啉衍生物，其中R1和R2为H，Me；R3为（2-6C）杂环脂肪环（1-4C）烷基，（2-5C）杂环芳基（1-4C）烷基，（6C）芳基（1-4C）烷基，（1-4C）（二）烷基氨基甲酰氨基（2-4C）烷基，（2-6C）杂环脂肪环甲酰氨基（2-4C）烷基，R5-（2-4C）烷基或R5-羰基（1-4C）烷基；R4为（2-5C）杂环芳基，（6C）芳基，（3-8C）环烷基，（2-6C）杂环脂肪环或（1-6C）烷基，R5为（二）（1-4C）烷基氨基，（1-4C）烷氧基，氨基，羟基，（6C）芳基氨基，（二）（3-4C）烯基氨基，（2-5C）杂环芳基（1-4C）烷基氨基，（6C）芳基（1-4C）烷基氨基，（二）[(1-4C）烷氧基（2-4C）烷基]氨基，（二）[(1-4C）烷基氨基（2-4C）烷基]氨基，（二）[氨基（2-4C）烷基]氨基或（二）[羟基（2-4C）烷基]氨基。本发明还涉及包含所述衍生物的制药组合物，以及使用这些衍生物调节生育能力的用途。
• TSH receptor antagonizing tetrahydroquinoline compounds
  申请人：Karstens Willem Frederik Johan

  公开号：US20110172267A1

  公开（公告）日：2011-07-14

  The present invention relates the use of a compound, a pharmaceutical composition, compounds and a kit for treating or preventing disorders in a mammal responsive to TSH receptor mediated pathways, including disorders such as hyperthyroidism, Graves' disease, Graves Ophthalmopathy, Graves' associated pretibial dermopathy, nodular goitre and thyroid cancer comprising administering to said mammal an effective amount of a tetrahydroquinoline compound of Formula (I) or an pharmaceutically acceptable salt thereof.

  本发明涉及使用一种化合物，一种药物组合物，化合物和用于治疗或预防哺乳动物中对TSH受体介导途径有反应的疾病的工具包，包括过度活跃甲状腺，格雷夫斯病，格雷夫斯眼病，格雷夫斯相关的胫骨前皮肤病，结节性甲状腺肿和甲状腺癌，其包括向该哺乳动物施加有效量的公式（I）的四氢喹啉化合物或其药学上可接受的盐。