Unlock instant, AI-driven research and patent intelligence for your innovation.
Chirality n-heterocyclic carbine precursor compound with benzoglioxaline frameworks and preparation method and application thereof
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A technology of precursor compounds and chiral azapines, which is applied in the direction of hydrocarbons, hydrocarbons, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of benzimidazole carbene ligands, which are less researched and still exist. In the initial stage and other problems, to achieve the effect of superior reactivity
Active Publication Date: 2018-08-28
ZHEJIANG UNIV CITY COLLEGE
View PDF4 Cites 2 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
[0003] For now, whether it is monodentate or bidentate chiral NHC ligands developed by research groups at home and abroad, its basic structural units are mainly based on the structure of five-membered ring imidazole or dihydroimidazole, among which as one of the representative skeletons The research on benzimidazole carbene ligands is less and is still in its infancy
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 1
[0071] Preparation and characterization of compound Ⅱ-1:
[0072]
[0073] Compound Ⅰ-1 (521 μL, 4 mmol) and triethylamine (1112 μL, 8 mmol) were dissolved in dry dichloromethane (40 mL), and after stirring at room temperature for 5 minutes, tert-butyldimethylsilyl chloride (663 mg, 4.4 mmol), after stirring for 5 minutes, 4-dimethylaminopyridine (489 μL, 4 mmol) was added and reacted at room temperature for 3 hours. The reaction solution was evaporated to dryness under reduced pressure, and the mixture was separated by column chromatography (CH 2 Cl 2 :CH 3 OH=80:1~50:1), 656 mg of yellow oily substance II-1 was obtained with a yield of 71%. 1 H NMR (500MHz, CDCl 3 )δ: 3.76(dd, J=9.8, 3.2Hz, 1H), 3.40–3.31(m, 1H), 2.57(dd, J=8.8, 3.2Hz, 1H), 0.91(d, J=3.0Hz, 18H ), 0.07(s,6H).
Embodiment 2
[0075] Preparation and characterization of compound Ⅱ-2:
[0076]
[0077] The preparation conditions were the same as in Example 1, yellow oil, and the yield was 85%; 1 HNMR (500MHz, CDCl 3 )δ: 7.38 (dd, J = 8.3, 1.3Hz, 2H), 7.36–7.32 (m, 2H), 7.29–7.24 (m, 1H), 4.08 (dd, J = 8.4, 3.9Hz, 1H), 3.73 (dd, J=9.8, 4.0Hz, 1H), 3.53(dd, J=9.8, 8.4Hz, 1H), 0.94–0.86(m, 9H), 0.03(t, J=2.2Hz, 6H).
Embodiment 3
[0079] Preparation and characterization of compound Ⅱ-3:
[0080]
[0081] The preparation conditions were the same as in Example 1, yellow oil, and the yield was 88%; 1 HNMR (500MHz, CDCl 3 )δ: 7.33–7.28(m,2H),7.25–7.19(m,3H),3.59(dd,J=9.7,4.4Hz,1H),3.45(dd,J=9.7,6.5Hz,1H),3.10 (m,1H),2.80(dd,J=13.4,5.3Hz,1H),2.52(dd,J=13.4,8.4Hz,1H),0.94–0.91(m,9H),0.09–0.05(m,6H ).
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
Abstract
The invention discloses chirality n-heterocyclic carbine precursor compound with benzoglioxaline frameworks and a preparation method and application thereof. Five steps of reaction can simply and effectively compound a series of chirality benzoglioxaline carbine precursor compound with novel structures, oxygen-containing functional groups containing lone pair electrons are be introduced into substituent groups of chirality side chains, the ligands can serve as bi-dentate ligands to combine with a metal center to form a complex compound, excellent reactive activation can show up in a metalcatalysisreaction system, and a catalytic product with a high-mapping isomer can be hopefully obtained in an asymmetric reaction.
Description
technical field [0001] The invention relates to the field of organic synthesis, in particular to a chiral nitrogen-heterocyclic carbene precursor compound with a benzimidazole skeleton and a preparation method and application thereof. Background technique [0002] The research history of N-heterocyclic carbenes (NHCs) can be traced back to Wanzlick’s first report in 1962, but it was not until 1991 that Arduengo et al. first isolated and obtained stable NHC monomers—imidazole-2-carbene, NHCs Ligand research has attracted widespread attention. Compared with phosphine ligands, azacarbene ligands have the following characteristics: 1) Stronger σ-donating properties and weaker π-accepting properties enable NHC to form more stable metal complexes with transition metals, and exhibit Better air and thermodynamic stability; 2) Different from the spatial layout of the "edge-to-face" phosphine ligand, the five-membered nitrogen heterocyclic carbene ligand has a wedge-shaped near-plana...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More