(4S)-4,5-dihydro-2-(8'-quinolinyl)-4-benzyl-oxazole | 220628-97-7

• 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: (4S)-4,5-dihydro-2-(8'-quinolinyl)-4-benzyl-oxazole
• 英文别名: (4'R)-8-(3',4'-dihydro-4'-benzyl-2'-oxazolyl)quinoline；Quinoline, 8-[(4S)-4,5-dihydro-4-(phenylmethyl)-2-oxazolyl]-；(4S)-4-benzyl-2-quinolin-8-yl-4,5-dihydro-1,3-oxazole
• CAS: 220628-97-7
• 化学式: C₁₉H₁₆N₂O
• 分子量: 288.349
• InChiKey: UJADDXAPWQSGKQ-INIZCTEOSA-N

物化性质

• 沸点：
  479.5±18.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  ammonium hexafluorophosphate 、 (2-methylallyl)palladium-chloride dimer 、 (4S)-4,5-dihydro-2-(8'-quinolinyl)-4-benzyl-oxazole 以 乙醇 为溶剂， 以47%的产率得到(η(3)-2-methylallyl)[(4'R)-8-(3',4'-dihydro-4'-benzyl-2'-oxazolyl)quinoline-N,N]palladium(II) hexafluorophosphate
  参考文献：
  名称：

  Palladium Complexes with Chiral Oxazoline Ligands. Effect of Chelate Size on Catalytic Allylic Substitutions

  摘要：

  Mono- and bimetallic allylic palladium complexes (1L-5L) with L being chiral bidentate oxazoline ligands (from pyridine (a-d), quinoline (e-g), and piperazine (h)), containing different kinds of allyl groups (1-5), were easily obtained, and their structures in solution were elucidated by NMR spectroscopy. Complex 1d was also characterized by X-ray diffraction. The activity of these complexes in palladium-catalyzed allylic alkylation for acyclic and cyclic substrates was tested. For catalytic systems with ligands a-g, the activity was very high, although the enantioselectivity was low for pyridine derivatives and moderate for quinolino-oxazoline ligands, showing the beneficial effect of chelate size in the latter case. In contrast, the palladium tetraaza catalytic system (Pd/h) exhibited a low activity and a low asymmetric induction. Allylic complexes 1a, 1d, and 1e were also active in the Pd-catalyzed allylic amination, but the activity of these systems was lower than for the alkylations. Under in situ catalytic conditions, the coordination competition of the benzylamine with the bidentate ligand led to different results than using previously isolated precursors.

  DOI：

  10.1021/om990625+
• 作为产物：
  描述：

  (1'S)-N-(1'-benzyl-2'-hydroxyethyl)-8-quinolinecarboxamide 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 16.0h， 生成 (4S)-4,5-dihydro-2-(8'-quinolinyl)-4-benzyl-oxazole
  参考文献：
  名称：

  Chiral quinolinyl-oxazolines as ligands for copper(I)-catalyzed asymmetric cyclopropanation

  摘要：

  Chiral quinolinyl-oxazoline compounds have been synthesized from enantiomerically pure amino alcohols and 8-quinoline-carboxylic acid using a convenient procedure. Asymmetric cyclopropanation of styrene with diazo-acetates in the presence of 1 mol% of CuOTf and quinolinyl-oxazolines gave 2-phenylcyclopropane carboxylates in moderate enantiomeric excesses. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00455-8
• 作为试剂：
  描述：

  降冰片烯 、 4-碘甲苯 在 三乙胺 甲酸 、 palladium diacetate 、 (4S)-4,5-dihydro-2-(8'-quinolinyl)-4-benzyl-oxazole 作用下， 以 二甲基亚砜 为溶剂， 反应 60.0h， 以79%的产率得到2-(4-methylphenyl)bicyclo[2.2.1]heptane
  参考文献：
  名称：

  手性喹啉基-恶唑啉的钯配合物催化降冰片烯衍生物的不对称加氢芳基化

  摘要：

  已发现手性喹啉基-恶唑啉是降冰片烯及其衍生物的对映选择性钯催化的Heck型加氢芳基化反应中的有效配体。在恶唑啉环上具有中等大小烷基的配体提供更高的对映选择性。芳基碘化物上供电子性取代基的存在增加了反应的选择性和产率。（-）-外-2-基苯基二环[2.2.1]庚烷的构型已被指定为（1 R，2 R）。

  DOI：

  10.1016/s0957-4166(01)00436-0

文献信息

• Chiral quinolinyl-oxazolines as ligands for copper(I)-catalyzed asymmetric cyclopropanation
  作者：Xin-Yan Wu、Xiang-Hong Li、Qi-Lin Zhou

  DOI：10.1016/s0957-4166(98)00455-8

  日期：1998.12

  Chiral quinolinyl-oxazoline compounds have been synthesized from enantiomerically pure amino alcohols and 8-quinoline-carboxylic acid using a convenient procedure. Asymmetric cyclopropanation of styrene with diazo-acetates in the presence of 1 mol% of CuOTf and quinolinyl-oxazolines gave 2-phenylcyclopropane carboxylates in moderate enantiomeric excesses. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Palladium Complexes with Chiral Oxazoline Ligands. Effect of Chelate Size on Catalytic Allylic Substitutions
  作者：Josep Maria Canal、Montserrat Gómez、Francisco Jiménez、Mercè Rocamora、Guillermo Muller、Elisabet Duñach、Delphine Franco、Alicia Jiménez、F. H. Cano

  DOI：10.1021/om990625+

  日期：2000.3.1

  Mono- and bimetallic allylic palladium complexes (1L-5L) with L being chiral bidentate oxazoline ligands (from pyridine (a-d), quinoline (e-g), and piperazine (h)), containing different kinds of allyl groups (1-5), were easily obtained, and their structures in solution were elucidated by NMR spectroscopy. Complex 1d was also characterized by X-ray diffraction. The activity of these complexes in palladium-catalyzed allylic alkylation for acyclic and cyclic substrates was tested. For catalytic systems with ligands a-g, the activity was very high, although the enantioselectivity was low for pyridine derivatives and moderate for quinolino-oxazoline ligands, showing the beneficial effect of chelate size in the latter case. In contrast, the palladium tetraaza catalytic system (Pd/h) exhibited a low activity and a low asymmetric induction. Allylic complexes 1a, 1d, and 1e were also active in the Pd-catalyzed allylic amination, but the activity of these systems was lower than for the alkylations. Under in situ catalytic conditions, the coordination competition of the benzylamine with the bidentate ligand led to different results than using previously isolated precursors.