9-epi-O-1,10-phenanthrolin-2-ylquinine | 1502715-18-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: 9-epi-O-1,10-phenanthrolin-2-ylquinine
• 英文别名: 2-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]-1,10-phenanthroline
• CAS: 1502715-18-5
• 化学式: C₃₂H₃₀N₄O₂
• 分子量: 502.616
• InChiKey: RINLBCUHPBVAKG-VXATVOGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  60.37
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-氯-1,10-菲咯啉 、 9-epiquinine 在 lithium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 25.0h， 以67%的产率得到9-epi-O-1,10-phenanthrolin-2-ylquinine
  参考文献：
  名称：

  模块化手性支架的简单方法：将功能性硫亲核试剂与金鸡纳生物碱结合

  摘要：

  在金鸡纳生物碱支架上选择性和立体选择性地连接了一系列功能模块。硫醇盐与生物碱甲磺酸盐和环氧化物的S N 2反应引入了金属络合部分，包括吡啶和1,10-菲咯啉的杂环系统。在另外的步骤中形成了各自的氢键供体的硫脲和萨拉烷基序。在金属催化的亨利和Tsuji-Trost反应中测试了改性的金鸡纳生物碱。

  DOI：

  10.1016/j.tet.2015.05.035
• 作为试剂：
  描述：

  反式肉桂醛 、 硝基甲烷 在 N-甲基吗啉 、 copper(II) choride dihydrate 、 9-epi-O-1,10-phenanthrolin-2-ylquinine 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 17.0h， 以86%的产率得到
  参考文献：
  名称：

  Synthesis and computation of diastereomeric phenanthroline–quinine ligands and their application in asymmetric Henry reaction

  摘要：

  A class of chiral ligands has been developed by combining phenanthroline with quinine in a one-step method that does not require resolution. The synthesized three ligands were then coordinated with Cu-(II) and the performance of the resultant chiral catalysts in the asymmetric Henry reaction was evaluated. Moderate to good yields (up to 86%) with high enantioselectivities (up to 99% ee) were observed in the reactions catalyzed by one of the three catalysts. Theoretical calculations were performed to analyze the catalytic activities of the different Cu-(II)-ligand catalysts. Three different ligands were investigated and one ligand was found to adopt an unexpected five-coordinated mode; the second coordinated with two nitrogen atoms of phenanthroline to give a complex, which activated both substrates of Henry reaction; the third was unable to form a complex with Cu-(II). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.010

文献信息

• Synthesis and computation of diastereomeric phenanthroline–quinine ligands and their application in asymmetric Henry reaction
  作者：Lili Zhang、Hao Wu、Zhongyue Yang、Xiufang Xu、Haitao Zhao、Yaodong Huang、Yongmei Wang

  DOI：10.1016/j.tet.2013.10.010

  日期：2013.12

  A class of chiral ligands has been developed by combining phenanthroline with quinine in a one-step method that does not require resolution. The synthesized three ligands were then coordinated with Cu-(II) and the performance of the resultant chiral catalysts in the asymmetric Henry reaction was evaluated. Moderate to good yields (up to 86%) with high enantioselectivities (up to 99% ee) were observed in the reactions catalyzed by one of the three catalysts. Theoretical calculations were performed to analyze the catalytic activities of the different Cu-(II)-ligand catalysts. Three different ligands were investigated and one ligand was found to adopt an unexpected five-coordinated mode; the second coordinated with two nitrogen atoms of phenanthroline to give a complex, which activated both substrates of Henry reaction; the third was unable to form a complex with Cu-(II). (C) 2013 Elsevier Ltd. All rights reserved.
• Simple approach to modular chiral scaffolds: binding functional sulfur nucleophiles to Cinchona alkaloids
  作者：Mariola Zielińska-Błajet、Przemysław J. Boratyński、Łukasz Sidorowicz、Jacek Skarżewski

  DOI：10.1016/j.tet.2015.05.035

  日期：2016.5

  stereoselectively attached to the Cinchona alkaloid scaffolds. The SN2 reactions of thiolates with alkaloid mesylate and epoxide introduced metal-complexing moieties, including the heterocyclic systems of pyridine and 1,10-phenanthroline. The respective H-bond donating thiourea and salane motifs were formed in an additional step. The modified Cinchona alkaloids were tested in the metal-catalyzed Henry and

  在金鸡纳生物碱支架上选择性和立体选择性地连接了一系列功能模块。硫醇盐与生物碱甲磺酸盐和环氧化物的S N 2反应引入了金属络合部分，包括吡啶和1,10-菲咯啉的杂环系统。在另外的步骤中形成了各自的氢键供体的硫脲和萨拉烷基序。在金属催化的亨利和Tsuji-Trost反应中测试了改性的金鸡纳生物碱。