8-(2-methylphenyl)quinoline | 57479-11-5

• 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
• 英文名称: 8-(2-methylphenyl)quinoline
• CAS: 57479-11-5
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: LJNMSEZWDSYWIT-UHFFFAOYSA-N

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-(2-methylphenyl)quinoline 、 (2-溴乙炔基)三异丙基硅烷 在 potassium dihydrogenphosphate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 溶剂黄146 作用下， 反应 24.0h， 以81%的产率得到8-(2-methyl-6-((triisopropylsilyl)ethynyl)phenyl)quinoline
  参考文献：
  名称：

  Substrate‐Rhodium Cooperativity in Photoinduced ortho ‐Alkynylation of Arenes

  摘要：

  AbstractIn the realm of metallaphotocatalytic C−H activation strategy, the direct excitation of the transition metal which plays the dual role of light energy harnessing alongside performing the bond breaking and forming is a rare phenomenon. In this context we have developed the first photo‐induced Rh‐catalyzedortho‐alkynylation under ambient conditions without the requirement of silver salt, photocatalyst (PC) or any engineered substrate or catalyst. The transformation functions by the specific cooperative effect of a six‐membered rhodacycle which is the photo‐responsive species. The catalytic system allows the conjugation of arenes with sp3‐rich pharmacophoric fragments. The control experiments as well as the computational studies resolve the mechanistic intricacies for this transformation. An outer sphere electron transfer process from Rh to alkynyl radical is operative for the present photo‐induced transformation over the more common oxidative addition or 1,2‐migratory insertion pathways.

  DOI：

  10.1002/anie.202210492
• 作为产物：
  描述：

  8-巯基喹啉 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 16.5h， 生成 8-(2-methylphenyl)quinoline
  参考文献：
  名称：

  通过分子内自由基ipso取代反应合成联芳基

  摘要：

  使用磺酰胺和磺酸酯衍生的束缚链，通过分子内自由基[1,5] -ipso取代制备各种官能化的联芳基和杂联芳基。该方法的总效率由芳族受体环上适当定位的取代基决定。该方法的扩展来苄基磺酸酯和它们的相应Ñ -methylsulfonamide替代作为底物在潜在[1,6] -本位3'-取代反应引线主要以替代[1,7]加成产物。

  DOI：

  10.1016/j.tet.2015.07.048

文献信息

• Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations
  作者：Surendra Thapa、Santosh K. Gurung、Diane A. Dickie、Ramesh Giri

  DOI：10.1002/anie.201407586

  日期：2014.10.20

  An efficient copper(I)‐catalyzed coupling of triaryl and trialkylindium reagents with aryl iodides and bromides is reported. The reaction proceeds at low catalyst loadings (2 mol %) and generally only requires 0.33 equivalents of the triorganoindium reagent with respect to the aryl halide as all three organic nucleophilic moieties of the reagent are transferred to the products through consecutive transmetalations

  据报道，三芳基和三烷基铟试剂与芳基碘化物和溴化物的高效铜（I）催化偶联。反应在低催化剂负载量（2mol％）下进行，并且相对于芳基卤化物，通常仅需要0.33当量的三有机铟试剂，因为试剂的所有三个有机亲核部分都通过连续的重金属化作用转移到产物中。该反应耐受各种官能团和空间受阻的底物。此外，涉及潜在反应中间体的合成和表征的初步机理研究提供了构成催化循环的基本步骤的一瞥。
• Catalytic asymmetric hydrogenation of quinoline carbocycles: unusual chemoselectivity in the hydrogenation of quinolines
  作者：Ryoichi Kuwano、Ryuhei Ikeda、Kazuki Hirasada

  DOI：10.1039/c5cc01971k

  日期：——

  A chiral PhTRAP–ruthenium catalyst selectively hydrogenates the quinoline carbocycles to afford 5,6,7,8-tetrahydroquinolines with up to 91 : 9 er.

  一个手性PhTRAP-钌催化剂选择性地加氢喹啉环，生成了5,6,7,8-四氢喹啉，其对映选择性高达91:9。
• METHOD FOR PRODUCING UNSATURATED ORGANIC COMPOUND
  申请人：Asaumi Taku

  公开号：US20110046380A1

  公开（公告）日：2011-02-24

  A method for producing an unsaturated organic compound represented by the formula (3): (Y 1 ) m-1 —R 1 —R 2 —(Y 2 ) n-1 (3) wherein Y 1 represents R 2 or X 1 , and Y 2 represents R 1 or B(X 2 ) 2 , which comprises reacting a compound represented by the formula (1): R 1 (X 1 ) m (1) wherein R 1 represents an aromatic group or the like, X 1 represents a leaving group and m represents 1 or 2, with a compound represented by the formula (2): R 2 B(X 2 ) 2 } n (2) wherein R 2 represents an aromatic group or the like, X 2 represents a hydroxyl group or the like, and n represents 1 or 2, in the presence of (a) a nickel compound selected from a nickel carboxylate, nickel nitrate and a nickel halide, (b) a phosphine compound such as 1,4-bis(dicyclohexylphosphino) butane, (c) an amine selected from a primary amine and a diamine such as N,N,N′,N′-tetramethyl-1,2-ethanediamine, and (d) an inorganic base.

  一种用于生产由公式(3)表示的不饱和有机化合物的方法：(Y1)m-1—R1—R2—(Y2)n-1(3)，其中Y1代表R2或X1，Y2代表R1或B(X2)2，包括在以下条件下反应由公式(1)表示的化合物：R1(X1)m(1)，其中R1代表芳香族基团或类似物，X1代表离开基团，m代表1或2，与由公式(2)表示的化合物反应：R2B(X2)2}n(2)，其中R2代表芳香族基团或类似物，X2代表羟基或类似物，n代表1或2，在存在(a)选择自镍羧酸盐、硝酸镍和卤化镍的镍化合物，(b)膦化合物，如1,4-双(二环己基膦基)丁烷，(c)选择自一次胺和二胺的胺，如N,N,N′,N′-四甲基-1,2-乙二胺，和(d)无机碱。
• Enantioselective Synthesis of Biaryl Atropisomers by Pd‐Catalyzed C−H Olefination using Chiral Spiro Phosphoric Acid Ligands
  作者：Jun Luo、Tao Zhang、Lei Wang、Gang Liao、Qi‐Jun Yao、Yong‐Jie Wu、Bei‐Bei Zhan、Yu Lan、Xu‐Feng Lin、Bing‐Feng Shi

  DOI：10.1002/anie.201902126

  日期：2019.5.13

  in the field of enantioselective C−H activation. Herein, we reported the synthesis of axially chiral biaryls by Pd‐catalyzed atroposelective C−H olefination. A novel chiral spiro phosphoric acid, STRIP, was identified as a superior ligand for this transformation. A broad range of axially chiral quinoline derivatives were synthesized in good yields with excellent enantioselectivities (up to 98 % ee)

  同时调节反应性和有效控制立体选择性的合适配体的发现是对映选择性CH活化领域的中心课题。在本文中，我们报道了通过Pd催化的Atrooselective CH烯化合成轴向手性联芳基。新型手性螺磷酸STRIP被确定为该转化的优良配体。以高收率和优异的对映选择性（高达98％ee）合成了多种轴向手性喹啉衍生物。使用密度泛函理论来获得对该反应中对映选择性的理论理解。
• Suzuki−Miyaura Coupling of Aryl Tosylates Catalyzed by an Array of Indolyl Phosphine−Palladium Catalysts
  作者：Chau Ming So、Chak Po Lau、Albert S. C. Chan、Fuk Yee Kwong

  DOI：10.1021/jo8014819

  日期：2008.10.3

  A family of indolyl phosphine ligands was applied to Suzuki-Miyaura cross-coupling of aryl tosylates. Catalyst loading can be reduced to 0.2 mol % for coupling of nonactivated aryl tosylate. A challenging example for room temperature coupling is realized. The scope of this highly active Pd/L2 system can be extended to other boron nucleophiles, including trifluoroborate salts and boronate esters. The ligand structural comparisons toward the reactivity in tosylate couplings are also described.