(1R,5S)-(+)-(2,3-b)-pineno-1,10-phenanthroline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: (1R,5S)-(+)-(2,3-b)-pineno-1,10-phenanthroline
• 英文别名: (1R,17R)-18,18-dimethyl-3,6-diazapentacyclo[15.1.1.02,15.04,13.05,10]nonadeca-2(15),3,5(10),6,8,11,13-heptaene
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: KXQGYTZHFQLASZ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)copper(I) perchlorate 、 (1R,5S)-(+)-(2,3-b)-pineno-1,10-phenanthroline 以 乙腈 为溶剂， 以96%的产率得到[Cu((1R,5S)-(2,3-b)-pineno-1,10-phenanthroline)2]ClO4
  参考文献：
  名称：

  非对映选择性形成和手性铜（I）菲咯啉配合物的光物理行为。

  摘要：

  （1R，5S）-（+）-和（1S，5R）-（-）-nopinone与8-氨基喹啉-7-甲醛的Friedländer缩合反应生成对映体纯的（2,3-b）-pineno- 1,10-菲咯啉。这些配体与Cu（I）的配位提供了不可相互转化的手性络合物，在其CD光谱中显示出相同和相反的Cotton效应，以及+0.37 V的相同半波氧化电位和442 nm处的MLCT吸收。两种络合物在298和77 K时均无发射。用光学纯的Delta-和Lambda- [Ru（bpy）（3）]（2+）和外消旋[Ru（dpb）（3）]进行Stern-Volmer猝灭研究。 （2+）作为供体（bpy = 2,2'-联吡啶和dpb = 4,4'-二苯基-bpy）。两项研究均未提供对映选择性淬灭的任何证据，

  DOI：

  10.1021/ic971267a

文献信息

• Metal-organic frameworks containing nitrogen-donor ligands for efficient catalytic organic transformations
  申请人：The University of Chicago

  公开号：US10647733B2

  公开（公告）日：2020-05-12

  Metal-organic framework (MOFs) compositions based on nitrogen donor-based organic bridging ligands, including ligands based on 1,3-diketimine (NacNac), bipyridines and salicylaldimine, were synthesized and then post-synthetically metalated with metal precursors, such as complexes of first row transition metals. Metal complexes of the organic bridging ligands could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

  基于以氮为供体的有机桥联配体，包括基于1,3-二酮亚胺（NacNac）、联吡啶和柳酸亚胺的金属-有机框架（MOFs）组成物被合成，然后用金属前驱体如第一行过渡金属的络合物进行后合成金属化。有机桥联配体的金属络合物也可以直接并入MOFs中。MOFs提供了一个多功能的、可回收和可重复使用的单点固体催化剂家族，用于催化各种不对称有机转化。这些固体催化剂也可以集成到流动反应器或超临界流体反应器中。
• Heterogeneous and homogeneous asymmetric electrocatalytic hydrogenation with rhodium(III) complexes containing chiral polypyridyl ligands
  作者：Jean-Claude Moutet、Liu Yao Cho、Carole Duboc-Toia、Ste´phane Me´nage、Elvira C. Riesgo、Randolph P. Thummel

  DOI：10.1039/a904477i

  日期：——

  of a rhodium complex containing a pyrrole-substituted chiral 2,2′-bipyridine ligand. The latter device gave the best results in terms of catalytic efficiency, turnover number (up to 4750) and asymmetric induction (up to 20% ee). From the viewpoint of catalytic efficiency and asymmetric induction, the electrocatalytic system compares well with asymmetric transfer hydrogenation catalyzed by rhodium complexes

  在均相介质或介质中研究了苯乙酮和2-丁酮与[Rh（L）2 Cl 2 ] +配合物（L为手性2,2'-联吡啶或1,10-菲咯啉）在水性电解质中的电催化氢化。在碳电极上涂覆有聚合物薄膜，该聚合物薄膜是通过含吡咯取代的手性2,2'-联吡啶配体的铑配合物的氧化电聚合制备的。后一种装置在催化效率，周转数（最高4750）和不对称感应（最高20％ee）方面给出了最佳结果。从催化效率和不对称诱导的角度来看，电催化体系与含相同配体的铑配合物催化的不对称转移氢化具有很好的比较。
• METAL-ORGANIC FRAMEWORKS CONTAINING NITROGEN-DONOR LIGANDS FOR EFFICIENT CATALYTIC ORGANIC TRANSFORMATIONS
  申请人：The University of Chicago

  公开号：US20170182486A1

  公开（公告）日：2017-06-29

  Metal-organic framework (MOFs) compositions based on nitrogen donor-based organic bridging ligands, including ligands based on 1,3-diketimine (NacNac), bipyridines and salicylaldimine, were synthesized and then post-synthetically metalated with metal precursors, such as complexes of first row transition metals. Metal complexes of the organic bridging ligands could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.
• CHIRAL LIGAND-BASED METAL-ORGANIC FRAMEWORKS FOR BROAD-SCOPE ASYMMETRIC CATALYSIS
  申请人：The University of Chicago

  公开号：US20170173572A1

  公开（公告）日：2017-06-22

  Metal-organic framework (MOFs) compositions based on chiral phosphine-, chiral oxazoline-, chiral pyridine-, and chiral diene-derived organic bridging ligands were synthesized and then post-synthetically metalated with metal precursors such as Ru and Rh complexes. The metal complexes could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations, including the addition of arylboronic acids to α,β-unsaturated ketones and alkimines, the hydrogenation of substituted alkene and carbonyl compounds, and cyclization reactions. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.
• Diastereoselective Formation and Photophysical Behavior of a Chiral Copper(I) Phenanthroline Complex
  作者：Elvira C. Riesgo、Alberto Credi、Luisa De Cola、Randolph P. Thummel

  DOI：10.1021/ic971267a

  日期：1998.5.1

  identical MLCT absorptions at 442 nm. Both complexes are nonemissive at 298 and 77 K. Stern-Volmer quenching studies were carried out with optically pure Delta- and Lambda-[Ru(bpy)(3)](2+) and racemic [Ru(dpb)(3)](2+) as donors (bpy = 2,2'-bipyridine and dpb = 4,4'-diphenyl-bpy). Neither study provides any evidence of enantioselective quenching, indicating that energy or electron transfer may be occurring

  （1R，5S）-（+）-和（1S，5R）-（-）-nopinone与8-氨基喹啉-7-甲醛的Friedländer缩合反应生成对映体纯的（2,3-b）-pineno- 1,10-菲咯啉。这些配体与Cu（I）的配位提供了不可相互转化的手性络合物，在其CD光谱中显示出相同和相反的Cotton效应，以及+0.37 V的相同半波氧化电位和442 nm处的MLCT吸收。两种络合物在298和77 K时均无发射。用光学纯的Delta-和Lambda- [Ru（bpy）（3）]（2+）和外消旋[Ru（dpb）（3）]进行Stern-Volmer猝灭研究。 （2+）作为供体（bpy = 2,2'-联吡啶和dpb = 4,4'-二苯基-bpy）。两项研究均未提供对映选择性淬灭的任何证据，