(R)-2-(4,5-dihydro-4-phenyloxazol-2-yl)quinoline

• 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: (R)-2-(4,5-dihydro-4-phenyloxazol-2-yl)quinoline
• 英文别名: 2-(4'-(R)-phenyloxazolin-2'-yl)quinoline；2-[4-(R)-phenyl-4,5-dihydrooxazolin-2-yl]quinoline；(R)-4-phenyl-2-(quinolin-2-yl)-4,5-dihydrooxazole；(4R)-4-phenyl-2-quinolin-2-yl-4,5-dihydro-1,3-oxazole
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: OIFADUQNTPUCKK-KRWDZBQOSA-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：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(4,5-dihydro-4-phenyloxazol-2-yl)quinoline 、 cobalt(II) chloride 以 四氢呋喃 为溶剂， 以82%的产率得到2-[4'-(R)-phenyloxazolin-2'-yl]quinoline cobalt(II) chloride
  参考文献：
  名称：

  Pyridine–oxazoline and quinoline–oxazoline ligated cobalt complexes: Synthesis, characterization, and 1,3-butadiene polymerization behaviors

  摘要：

  A series of cobalt complexes supported by pyridine-oxazoline (Pyox) and quinoline-oxazoline (Quox) were synthesized. Determined by single crystal X-ray crystallography, complexes 6a and 7c adopted distorted octahedron and trigonal bipyramid geometries, respectively, while complex 6b existed as an ion pair comprised of [CoL2](2+) and [CoCl4](2-), in which the cationic and anionic moieties displayed distorted octahedron and tetrahedral geometries, respectively. Upon activation with ethylaluminium sesquichloride (EASC), these cobalt complexes exhibited high catalytic activity and cis-1,4-selectivity toward 1,3-butadiene polymerization. The selectivity of the catalytic system could be switched from cis-1,4 to 1,2-fashion via the addition of PPh3. The effects of ligand environment, polymerization temperature, and [Al]/[Co] ratio on the polymerization were investigated in detail. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.07.013
• 作为产物：
  描述：

  喹哪啶酸 在 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 (R)-2-(4,5-dihydro-4-phenyloxazol-2-yl)quinoline
  参考文献：
  名称：

  Pyridine–oxazoline and quinoline–oxazoline ligated cobalt complexes: Synthesis, characterization, and 1,3-butadiene polymerization behaviors

  摘要：

  A series of cobalt complexes supported by pyridine-oxazoline (Pyox) and quinoline-oxazoline (Quox) were synthesized. Determined by single crystal X-ray crystallography, complexes 6a and 7c adopted distorted octahedron and trigonal bipyramid geometries, respectively, while complex 6b existed as an ion pair comprised of [CoL2](2+) and [CoCl4](2-), in which the cationic and anionic moieties displayed distorted octahedron and tetrahedral geometries, respectively. Upon activation with ethylaluminium sesquichloride (EASC), these cobalt complexes exhibited high catalytic activity and cis-1,4-selectivity toward 1,3-butadiene polymerization. The selectivity of the catalytic system could be switched from cis-1,4 to 1,2-fashion via the addition of PPh3. The effects of ligand environment, polymerization temperature, and [Al]/[Co] ratio on the polymerization were investigated in detail. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.07.013
• 作为试剂：
  描述：

  4-氯查耳酮 、 二苯基环丙烯酮 在 bis(1,5-cyclooctadiene)nickel (0) 、 (R)-2-(4,5-dihydro-4-phenyloxazol-2-yl)quinoline 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以55%的产率得到
  参考文献：
  名称：

  镍（0）催化的环戊烯酮和α，β-不饱和酮/亚胺的对映选择性[3 + 2]环状。

  摘要：

  描述了Ni 0催化的环丙烯酮的化学和对映选择性[3 + 2]环加成以及α，β-不饱和酮/亚胺。该反应整合了环丙烯酮的CC键裂解和羰基/亚胺基团的对映选择性官能化，通过分子间CC活化，以优异的对映选择性（88-98％ee）为γ-烯基丁烯内酯和内酰胺提供了温和的方法。

  DOI：

  10.1002/anie.201913130

文献信息

• Enantioselective Palladium(II)‐Catalyzed Oxidative Aminofluorination of Unactivated Alkenes with Et ₄ NF⋅3 HF as a Fluoride Source
  作者：Chuanqi Hou、Pinhong Chen、Guosheng Liu

  DOI：10.1002/anie.201913100

  日期：2020.2.10

  reaction provides easy access to a wide array of enantiomerically enriched β-fluoropiperidines in good yields and with excellent enantioselectivity. Notably, Et4 NF⋅3 HF as a readily accessible nucleophilic fluoride source was found to play an essential role in the enantioselective control, and CsOCF3 also acts a key additive to improve the excellent ee value of products.

  已经开发出使用手性喹啉-恶唑啉（Quox）作为配体的未活化烯烃的第一种不对称PdII催化的氨基氟化。该反应可容易地以良好的收率和优异的对映选择性接近大量对映体富集的β-氟哌啶。值得注意的是，已发现Et4NF⋅3HF作为一种易于获得的亲核氟化物源，在对映选择性控制中起着至关重要的作用，而CsOCF3也是提高产品ee值的关键添加剂。
• Pyridine- and Quinoline-Based Gold(III) Complexes: Synthesis, Characterization, and Application
  作者：Ann Christin Reiersølmoen、Anne Fiksdahl

  DOI：10.1002/ejoc.202000139

  日期：2020.5.22

  Gold(III) complexes of a series of polydentate pyridine‐ and quinoline‐based ligands are prepared. The coordination ability of the pyridine and quinoline nitrogen atoms are different. All complexes are catalytically active in cyclopropanation of propargyl ester and styrene and outperform KAuCl4. Pyridine‐N decoordination may be a crucial step for generation of catalytic activity.

  制备了一系列多齿吡啶和喹啉基配体的金（III）配合物。吡啶和喹啉氮原子的配位能力不同。所有的配合物在炔丙基酯和苯乙烯的环丙烷化中均具有催化活性，其性能优于KAuCl 4。吡啶-N去配位可能是产生催化活性的关键步骤。
• Enantioselective Palladium-Catalyzed Diamination of Alkenes Using <i>N</i>-Fluorobenzenesulfonimide
  作者：Erica L. Ingalls、Paul A. Sibbald、Werner Kaminsky、Forrest E. Michael

  DOI：10.1021/ja4043406

  日期：2013.6.19

  An enantioselective Pd-catalyzed vicinal diamination of unactivated alkenes using N-fluorobenzenesulfonimide as both an oxidant and a source of nitrogen is reported. The use of Ph-pybox and Ph-quinox ligands afforded differentially protected vicinal diamines in good yields with high enantioselectivities. Mechanistic experiments revealed that the high enantioselectivity arises from selective formation

  报道了使用 N-氟苯磺酰亚胺作为氧化剂和氮源对未活化烯烃进行对映选择性 Pd 催化的邻位二胺化。Ph-pybox 和 Ph-quinox 配体的使用以良好的收率和高对映选择性提供了差异保护的邻二胺。机理实验表明，高对映选择性仅源于手性 Pd 配合物的四种可能的非对映异构氨基钯化产物中的一种的选择性形成。氨基钯络合物通过 X 射线晶体学表征。
• Steric effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation using chiral oxazolinylpyridines
  作者：Giorgio Chelucci、Serenella Medici、Antonio Saba

  DOI：10.1016/s0957-4166(99)00023-3

  日期：1999.2

  Eight new chiral oxazolinylpyridines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. Catalytic activity and enantioselectivity were found to be highly dependent upon the steric requirement of the substituent on the pyridine ring: enantioselectivity up to 92% has been obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Palladium-catalyzed allylic alkylation using pyridino-oxazolines and quinolino-oxazolines as ligands—influence of steric factors
  作者：Ulf Bremberg、Fredrik Rahm、Christina Moberg

  DOI：10.1016/s0957-4166(98)00346-2

  日期：1998.10

  Four new chiral pyridino- and quinolino-oxazolines were subjected to the palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate. The enantioselectivity varied (82-88% ee) with the steric properties of the ligands. The results are discussed in connection with results previously obtained using analogous ligands. (C) 1998 Elsevier Science Ltd. All rights reserved.