(S)-N-(1-hydroxy-3,3-dimethylbutan-2-yl)quinoline-8-carboxamide | 220628-90-0

• 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: (S)-N-(1-hydroxy-3,3-dimethylbutan-2-yl)quinoline-8-carboxamide
• 英文别名: N-[(2S)-1-hydroxy-3,3-dimethylbutan-2-yl]quinoline-8-carboxamide
• CAS: 220628-90-0
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: SAVNWWOBXTXNIE-CYBMUJFWSA-N

物化性质

• 沸点：
  508.5±30.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-hydroxy-3,3-dimethylbutan-2-yl)quinoline-8-carboxamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1'S)-N-(1'-tert-butyl-2'-chloroethyl)-8-quinolinecarboxamide
  参考文献：
  名称：

  Chiral pyridylmethyl- and quinolinyl-oxazolines as ligands for enantioselective palladium-catalyzed allylic alkylation

  摘要：

  Chiral pyridylmethyl- and quinolinyl-oxazolines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enylacetate with dimethyl malonate. Enantioselectivities up to 77% were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00114-7
• 作为产物：
  描述：

  8-喹啉甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 32.0h， 生成 (S)-N-(1-hydroxy-3,3-dimethylbutan-2-yl)quinoline-8-carboxamide
  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

文献信息

• Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated γ-Lactam
  作者：Xianqing Wu、Jingping Qu、Yifeng Chen

  DOI：10.1021/jacs.0c07126

  日期：2020.9.16

  Herein, we report a nickel-catalyzed reductive cross-coupling reaction of easily accessible 3-butenyl carbamoyl chloride with primary alkyl iodide to access the chiral α-alkylated pyrrolidinone with broad substrate scope and high ee. The current art of synthesis still remains challenging on the enantioselective α-monoalkylation of pyrrolidinones. The newly designed chiral 8-quinoline imidazoline ligand

  在此，我们报告了镍催化的 3-丁烯基氨基甲酰氯与伯烷基碘的还原交叉偶联反应，以获得具有广泛底物范围和高 ee 的手性 α-烷基化吡咯烷酮。目前的合成技术对吡咯烷酮的对映选择性 α-单烷基化仍然具有挑战性。新设计的手性 8-喹啉咪唑啉配体（Quinim）对于保持反应性和对映选择性至关重要，以确保单取代烯烃的还原环化，从而前所未有地合成手性非芳香杂环。
• Nickel‐Catalyzed Enantioselective Reductive Alkyl‐Carbamoylation of Internal Alkenes
  作者：Xianqing Wu、Aneta Turlik、Baixue Luan、Feng He、Jingping Qu、K. N. Houk、Yifeng Chen

  DOI：10.1002/anie.202207536

  日期：2022.9.5

  The enantioselective reductive dicarbofunctionalization of internal alkenes has been developed to enable the formation of vicinal stereogenic centers. This protocol allows for facile synthesis of chiral pyrrolidinones bearing vicinal or quaternary stereocenters with excellent enantio- and diastereoselectivities. DFT calculations suggest that the enantiodetermining step is intramolecular migratory insertion

  内部烯烃的对映选择性还原二碳官能化已被开发以能够形成邻位立体中心。该方案可以轻松合成带有邻位或四元立体中心的手性吡咯烷酮，具有优异的对映选择性和非对映选择性。 DFT 计算表明对映决定步骤是氨基甲酰基-Ni 中间体的分子内迁移插入。
• Nickel/Quinim Enabled Asymmetric <scp>Carbamoyl‐Acylation</scp> of Unactivated Alkenes
  作者：Xianqing Wu、Haiyan Li、Feng He、Jingping Qu、Yifeng Chen

  DOI：10.1002/cjoc.202200856

  日期：——

  difunctionalization of tethered alkene has emerged as a prevailing tool for the expedient construction of synthetically valuable cyclic compounds. However, most efforts have been devoted to the reaction of styrene-type substrates due to their rigid scaffold and high reactivity. With respect to the difunctionalization of nonaromatic tethered olefin, especially the mono-substituted alkene, still remains largely

  过渡金属催化的系链烯烃双官能化已成为快速构建具有合成价值的环状化合物的常用工具。然而，由于苯乙烯类底物的刚性支架和高反应性，大多数努力都集中在苯乙烯类底物的反应上。关于非芳族系链烯烃，特别是单取代烯烃的双官能化，仍然很大程度上尚未开发。在此，我们公开了镍/奎宁络合物以及TBADT辅助催化的未活化烯烃与不同醛系在非芳族氨基甲酰氯上的不对称氨基甲酰酰化。该反应具有广泛的底物范围、良好的官能团耐受性、以及高反应效率和对映选择性。均为单取代且 1，在当前方案下，1-取代的烯烃可以与脂肪族或芳香族醛很好地合作，从而方便地获得一系列具有可转换酰基官能团的药用手性γ-内酰胺衍生物。该反应展示了手性Quinim配体在未来不对称催化转化中的更多应用可能性。
• 手性喹啉-咪唑啉配体的合成方法及其应用
  申请人：华东理工大学

  公开号：CN111925356B

  公开（公告）日：2023-04-28
• Chiral pyridylmethyl- and quinolinyl-oxazolines as ligands for enantioselective palladium-catalyzed allylic alkylation
  作者：Giorgio Chelucci、Serafino Gladiali、Antonio Saba

  DOI：10.1016/s0957-4166(99)00114-7

  日期：1999.4

  Chiral pyridylmethyl- and quinolinyl-oxazolines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enylacetate with dimethyl malonate. Enantioselectivities up to 77% were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.