(1'S)-N-(1'-methyl-2'-hydroxyethyl)-8-quinolinecarboxamide | 220628-86-4

• 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: (1'S)-N-(1'-methyl-2'-hydroxyethyl)-8-quinolinecarboxamide
• 英文别名: N-[(2S)-1-hydroxypropan-2-yl]quinoline-8-carboxamide
• CAS: 220628-86-4
• 化学式: C₁₃H₁₄N₂O₂
• mdl: MFCD21064756
• 分子量: 230.266
• InChiKey: LGTGVBHLGJRTHA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (1'S)-N-(1'-methyl-2'-hydroxyethyl)-8-quinolinecarboxamide 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以64%的产率得到(1'S)-N-(1'-methyl-2'-chloroethyl)-8-quinolinecarboxamide
  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 (1'S)-N-(1'-methyl-2'-hydroxyethyl)-8-quinolinecarboxamide
  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

• 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。
• 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.