8-methyl-5-phenylquinoline | 113431-48-4

• 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: 8-methyl-5-phenylquinoline
• CAS: 113431-48-4
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: UGUKGCLMKLTYOX-UHFFFAOYSA-N

物化性质

• 熔点：
  57.5-58.0 °C
• 沸点：
  357.9±11.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-methyl-5-phenylquinoline 在 亚硝酸特丁酯 、 氧气 、 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以81%的产率得到8-(nitromethyl)-5-phenylquinoline
  参考文献：
  名称：

  Palladium-Catalyzed sp³ C–H Nitration of 8-Methylquinolines

  摘要：

  Palladium-Catalyzed nitration of 8-methylquinolines with t-BuONO to give 8-(nitromethyl)quinolines in moderate to excellent yields has been developed involving an sp(3) C-H bond activation. The resulting (nitromethyl)quinolines could be Selectively reduced to (1,2,3,4-tetrahydroquinolin-8-yl)-methanamines by NaBH4 in the presence of a catalytic amount of NiCl2 center dot 6H(2)O.

  DOI：

  10.1021/acs.joc.5b00735
• 作为产物：
  描述：

  5-溴-8-甲基喹啉 、 苯硼酸 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三甲氧基磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以57%的产率得到8-methyl-5-phenylquinoline
  参考文献：
  名称：

  Pd-Catalyzed C–H Fluorination with Nucleophilic Fluoride

  摘要：

  The palladium-catalyzed C-H fluorination of 8-methylquinoline derivatives with nucleophilic fluoride is reported. This transformation involves the use of AgF as the fluoride source in combination with a hypervalent iodine oxidant. Both the scope and mechanism of the reaction are discussed.

  DOI：

  10.1021/ol301739f

文献信息

• Rh(<scp>iii</scp>)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds
  作者：Bidhan Ghosh、Rajarshi Samanta

  DOI：10.1039/c9cc02391g

  日期：——

  A straightforward Rh(III)-catalyzed general strategy was developed for the introduction of naphthol/phenol moieties to the C(sp3)–H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides. The developed method was further extended towards the arylation of 8-formylquinolines to accomplish diarylketone derivatives. The method is simple, relatively rapid, and chemo and regioselective

  开发了一种简单的Rh（III）催化的一般策略，即使用重氮萘-2（1 H）-ones /醌二叠氮化物将萘酚/苯酚部分引入8-甲基喹啉的C（sp 3）-H键。所开发的方法进一步扩展到8-甲酰基喹啉的芳基化反应，以完成二芳基酮衍生物。该方法简单，相对快速，并且具有广泛的范围和功能基团耐受性，具有化学和区域选择性。通过克规模的合成和生物活性分子的建设建立了合成实用程序。
• Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp³)−H and C(sp²)−H under Rhodium(III) Catalysis
  作者：Songjie Yu、Guodong Tang、Yingzi Li、Xukai Zhou、Yu Lan、Xingwei Li

  DOI：10.1002/anie.201602224

  日期：2016.7.18

  nitrogenation suffered from simple amidation/amination with limited atom‐economy and is mostly limited to C(sp2)−H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp2)−H and C(sp3)−H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl. A tridendate rhodium(III) complex has been isolated as the

  以前的直接CH H氮化反应受简单的酰胺化/胺化作用和原子经济的限制，并且大多限于C（sp 2）-H底物。在这项工作中，将蒽醌设计为在铑（III）催化下同时用于C（sp 2）-H和C（sp 3）-H键的新型双功能胺化试剂，从而提供了拴接到亲电羰基的亲核苯胺。已经分离出三登酸盐铑（III）配合物作为催化剂的静止状态，DFT研究确定了亚硝基物质的中间体。
• Cp*Co(III)-Catalyzed C(sp³)–H Bond Activation: A Highly Stereoselective and Regioselective Alkenylation of 8-Methylquinoline with Alkynes
  作者：Malay Sen、Balakumar Emayavaramban、Nagaraju Barsu、J. Richard Premkumar、Basker Sundararaju

  DOI：10.1021/acscatal.6b00612

  日期：2016.5.6

  Efficient, atom-economical, highly regioselective C(sp3)–H bond alkenylation of 8-methylquinoline catalyzed by (Cp*)Co(III) is reported. A well-defined, air-stable, molecular cobalt catalyst, Cp*Co(III), is employed for the first time in C(sp3)–H bond activation. The developed methodology is broadly applicable and tolerates a variety of functional groups, under mild conditions. Experimental and density

  报道了由（Cp *）Co（III）催化的高效的，原子经济的，高度区域选择性的C（sp 3）–H键的8-甲基喹啉C链烯基化反应。定义明确的，空气稳定的分子钴催化剂Cp * Co（III）首次用于C（sp 3）–H键活化。所开发的方法具有广泛的适用性，并且在温和的条件下可以耐受各种官能团。实验和密度泛函理论（DFT）结果表明，最初的环金属化是通过外部碱基辅助的协同金属化去质子化途径发生的。
• Palladium(<scp>ii</scp>)-catalyzed oxidative C(sp³)–P bond formation <i>via</i> C(sp³)–H bond activation
  作者：Lijin Chen、Zhenfei Zhou、Saifei Zhang、Xiaoqian Li、Xuebing Ma、Jiaxing Dong

  DOI：10.1039/c9cc07637a

  日期：——

  Disclosed herein is a Pd(II)-catalyzed C(sp3)–H/P–H oxidative cross-coupling reaction between 8-methylquinolines with H-phosphonates or diarylphosphine oxides via chelation-assisted C(sp3)–H bond activation. The protocol exhibits a relatively broad functional-group tolerance and exclusive chemo- and regioselectivity. Furthermore, detailed mechanistic studies support the proposed reaction pathway.

  本文公开了通过螯合辅助的C（sp 3）-H键活化作用，Pd（II）催化的8-甲基喹啉与H-膦酸酯或二芳基膦氧化物之间的Pd（II）催化的C（sp 3）-H / P-H氧化交叉偶联反应。。该协议表现出相对广泛的功能组耐受性和排他性的化学和区域选择性。此外，详细的机理研究支持所提出的反应途径。
• Rhodium(<scp>iii</scp>)-catalyzed regio- and stereoselective benzylic α-fluoroalkenylation with gem-difluorostyrenes
  作者：Lingheng Kong、Bingxian Liu、Xukai Zhou、Fen Wang、Xingwei Li

  DOI：10.1039/c7cc06048c

  日期：——

  Rhodium(III)-catalyzed mild benzylic α-fluoroalkenylation of 8-methylquinolines with gem-difluorostyrenes has been developed. This reaction occurred via C–H activation and C–F cleavage and is applicable to a wide range of substrates, leading to the synthesis of Z-alkenyl fluorides under mild and redox-neutral conditions with high regio- and stereoselectivity.

  已经开发了铑（III）与宝石-二氟苯乙烯的8-甲基喹啉的轻度苄基α-氟烯基化。该反应通过C–H活化和C–F裂解发生，适用于多种底物，导致在温和和氧化还原中性条件下具有高区域和立体选择性的Z-烯基氟化物的合成。