4-methyl-2-(4-(trifluoromethyl)phenyl)quinoline | 863487-46-1

• 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-methyl-2-(4-(trifluoromethyl)phenyl)quinoline
• 英文别名: 2-[4-(Trifluoromethyl)phenyl]-4-methylquinoline；4-methyl-2-[4-(trifluoromethyl)phenyl]quinoline
• CAS: 863487-46-1
• 化学式: C₁₇H₁₂F₃N
• 分子量: 287.284
• InChiKey: CXOCSORWAOWHAG-UHFFFAOYSA-N

物化性质

• 沸点：
  365.7±37.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(4-(trifluoromethyl)phenyl)quinoline 、 碳酸二甲酯 在 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到methyl {2-[4-(trifluoromethyl)phenyl]quinolin-4-yl}acetate
  参考文献：
  名称：

  WO2008/85301

  摘要：

  公开号：
• 作为产物：
  描述：

  2-羟基-4-甲基喹啉 在 4-二甲氨基吡啶 、 bis(triphenylphosphine)nickel(II) chloride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 4-methyl-2-(4-(trifluoromethyl)phenyl)quinoline
  参考文献：
  名称：

  Practical Ni-Catalyzed Cross-Coupling of Unsaturated Zinc Pivalates with Unsaturated Nonaflates and Triflates

  摘要：

  A practical nickel-catalyzed cross-coupling of (hetero)aryl or alkynylzinc pivalates with various unsaturated nonaflates or triflates is described. Organozinc pivalates allow these cross-couplings to take place with high yields and a low catalyst loading (0.5 mol %). Couplings with (E)- and (Z)-alkenyl triflates proceed with retention of configuration.

  DOI：

  10.1021/acs.orglett.8b03417

文献信息

• Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines
  作者：Mingbing Zhong、Song Sun、Jiang Cheng、Ying Shao

  DOI：10.1021/acs.joc.6b01910

  日期：2016.11.18

  An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C–H activation process under external-oxidant-free conditions.

  已开发了铁的芳基硝基酮与双取代的乙酸乙烯酯的铁催化的分子间[4 + 2]环化反应，用于合成2,4-二取代的喹啉，产率中等至良好，且具有良好的官能团相容性。初步的机理研究表明，在无外部氧化剂的条件下，铁催化的CH活化过程似乎是合理的。
• Nickel complexes supported by quinoline-based ligands: synthesis, characterization and catalysis in the cross-coupling of arylzinc reagents and aryl chlorides or aryltrimethylammonium salts
  作者：Qiang Zhang、Xue-Qi Zhang、Zhong-Xia Wang

  DOI：10.1039/c2dt30886j

  日期：——

  Lithium and nickel complexes bearing quinoline-based ligands have been synthesized and characterized. Reaction of 8-azidoquinoline with Ph2PNHR (R = p-MeC6H4, But) affords N-(8-quinolyl)iminophosphoranes RNHP(Ph2)N(8-C9H6N) (1a, R = p-MeC6H4; 1b, R = But. C9H6N = quinolyl)). Reaction of 1a with (DME)NiCl2 generates a nickel complex [NiCl2N(8-C9H6N)P(Ph2)NH(p-MeC6H4)}] (2a). Treatment of 1b with (DME)NiCl2 and following with NaH produces [NiCl(1,2-C6H4)P(Ph)(NHBut)N(8-C9H6N)}] (4). Complex 4 was also obtained by reaction of (DME)NiCl2 with [Li(1,2-C6H4)P(Ph)(NHBut)N(8-C9H6N)}] (5) prepared through lithiation of 1b. Reaction of 2-PyCH2P(Ph2)N(8-C9H6N) (6, Py = pyridyl) and PhNC(Ph)CH2P(Ph2)N(8-C9H6N) (8), respectively, with (DME)NiCl2 yields two five-coordinate N,N,N-chelate nickel complexes, [NiCl22-PyCH2P(Ph2)N(8-C9H6N)}] (7) and [NiCl2PhNC(Ph)CH2P(Ph2)N(8-C9H6N)}] (9). Similar reaction between Ph2PCH2P(Ph2)N(8-C9H6N) (10) and (DME)NiCl2 results in five-coordinate N,N,P-chelate nickel complex [NiCl2Ph2PCH2P(Ph2)N(8-C9H6N)}] (11). Treatment of [(8-C9H6N)NP(Ph2)]2CH2 (12) [prepared from (Ph2P)2CH2 and 2 equiv. of 8-azidoquinoline] with LiBun and (DME)NiCl2 successively affords [NiCl(8-C9H6N)NP(Ph2)}2CH] (13). The new compounds were characterized by 1H, 13C and 31P NMR spectroscopy (for the diamagnetic compounds), IR spectroscopy (for the nickel complexes) and elemental analysis. Complexes 2a, 4, 7, 9, 11 and 13 were also characterized by single-crystal X-ray diffraction techniques. The nickel complexes were evaluated for the catalysis in the cross-coupling reactions of arylzinc reagents with aryl chlorides and aryltrimethylammonium salts. Complex 7 exhibits the highest activity among the complexes in catalyzing the reactions of arylzinc reagents with either aryl chlorides or aryltrimethylammonium bromides.

  含喹啉基配体的锂和镍配合物已被合成和表征。8-叠氮喹啉与Ph2PNHR(R = p-MeC6H4, But)反应得到N-(8-喹啉基)亚氨基膦烷RNHP(Ph2)N(8-C9H6N)(1a, R = p-MeC6H4; 1b, R = But. C9H6N = 喹啉基))。1a与(DME)NiCl2反应生成镍配合物[NiCl2N(8-C9H6N)P(Ph2)NH(p-MeC6H4)}] (2a)。1b与(DME)NiCl2反应后，再用NaH处理得到[NiCl(1,2-C6H4)P(Ph)(NHBut)N(8-C9H6N)}] (4)。配合物4也可通过(DME)NiCl2与[Li(1,2-C6H4)P(Ph)(NHBut)N(8-C9H6N)}] (5)反应得到，后者是通过1b的锂化制备的。2-吡啶基甲基P(Ph2)N(8-C9H6N)(6, Py = 吡啶基)和PhNC(Ph)CH2P(Ph2)N(8-C9H6N)(8)分别与(DME)NiCl2反应，得到两个五配位的N,N,N-螯合镍配合物[NiCl22-PyCH2P(Ph2)N(8-C9H6N)}] (7)和[NiCl2PhNC(Ph)CH2P(Ph2)N(8-C9H6N)}] (9)。Ph2PCH2P(Ph2)N(8-C9H6N)(10)与(DME)NiCl2的类似反应生成五配位的N,N,P-螯合镍配合物[NiCl2Ph2PCH2P(Ph2)N(8-C9H6N)}] (11)。[(8-C9H6N)NP(Ph2)]2CH2(12)[由(Ph2P)2CH2和2当量的8-叠氮喹啉制备]依次与LiBun和(DME)NiCl2反应得到[NiCl(8-C9H6N)NP(Ph2)}2CH] (13)。新化合物通过1H、13C和31P NMR光谱(对于抗磁性化合物)、IR光谱(对于镍配合物)和元素分析进行表征。配合物2a、4、7、9、11和13还通过单晶X射线衍射技术进行表征。这些镍配合物被评估用于芳基锌试剂与芳基氯和芳基三甲基铵盐的交叉偶联反应的催化活性。在催化芳基锌试剂与芳基氯或芳基三甲基溴化铵的反应中，配合物7显示出最高的活性。
• Synthesis of Substituted 1,2-Dihydroquinolines and Quinolines from Aromatic Amines and Alkynes by Gold(I)-Catalyzed Tandem Hydroamination−Hydroarylation under Microwave-Assisted Conditions
  作者：Xin-Yuan Liu、Pan Ding、Jie-Sheng Huang、Chi-Ming Che

  DOI：10.1021/ol070814l

  日期：2007.7.1

  A method to efficiently prepare substituted 1,2-dihydroquinolines and quinolines by Au(I)-catalyzed tandem hydroamination-hydroarylation under microwave irradiation was developed. This method requires short reaction time (10-70 min) and has a broad substrate scope.

  开发了一种在微波辐射下通过Au（I）催化的串联加氢胺化-氢芳基化反应有效制备取代的1,2-二氢喹啉和喹啉的方法。该方法需要较短的反应时间（10-70分钟），并且具有广泛的底物范围。
• The synthesis of quinolines <i>via</i> denitrogenative palladium-catalyzed cascade reaction of <i>o</i>-aminocinnamonitriles with arylhydrazines
  作者：Jing Xie、Hang Huang、Tong Xu、Renhao Li、Jiuxi Chen、Xueting Ye

  DOI：10.1039/d0ra01043j

  日期：——

  example of the palladium-catalyzed cascade reaction of o-aminocinnamonitriles with arylhydrazines has been achieved, providing an efficient synthetic pathway to access quinolines with moderate to good yields. Preliminary mechanistic experiments indicate that this cascade process involves sequential denitrogenative addition followed by an intramolecular cyclization.

  已经实现了邻氨基肉桂腈与芳基肼的钯催化级联反应的第一个例子，为以中等至高产率获得喹啉提供了一种有效的合成途径。初步机械实验表明，这种级联过程涉及顺序脱氮加成，然后是分子内环化。
• Convenient Synthesis of Quinolines from α-2-Nitroaryl Alcohols and Alcohols via a Ruthenium-catalyzed Hydrogen Transfer Strategy
  作者：Feng Xie、Min Zhang、Mengmeng Chen、Wan Lv、Huanfeng Jiang

  DOI：10.1002/cctc.201402832

  日期：2015.1

  A new and straightforward method for convenient synthesis of quinolines via a ruthenium‐catalyzed hydrogen‐transfer strategy has been demonstrated. By employing a commercially available ruthenium catalyst system, different α‐2‐nitroaryl alcohols were efficiently converted in combination with a variety of alcohols into various substituted products in reasonable to good yields upon isolation. The synthetic

  已经证明了一种新的直接方法，可通过钌催化的氢转移策略方便地合成喹啉。通过使用可商购的钌催化剂体系，不同的α-2-硝基芳基醇与各种醇结合后，可以有效地转化成各种取代的产物，并在分离时以合理的收率得到良好的收率。合成规程操作简单，具有广泛的底物范围，并且不需要使用专门的还原剂，这使其成为用于多种喹啉衍生物的通用制备的实用方法。