A class of nad(p)h mimetics with a chiral cycloaryl alkanoline skeleton and its synthesis method and application

A synthetic method and simulant technology, applied in organic chemical methods, organic compound/hydride/coordination complex catalysts, chemical instruments and methods, etc., can solve problems such as poor stability, difficulty, cumbersome synthesis, etc.

Active Publication Date: 2021-07-06
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its ferrocene skeleton, the compound has poor stability, relatively cumbersome and difficult synthesis, and ideal reactivity

Method used

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  • A class of nad(p)h mimetics with a chiral cycloaryl alkanoline skeleton and its synthesis method and application
  • A class of nad(p)h mimetics with a chiral cycloaryl alkanoline skeleton and its synthesis method and application
  • A class of nad(p)h mimetics with a chiral cycloaryl alkanoline skeleton and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of compound 2

[0047]

[0048] Under nitrogen protection, compound 1 (1.900g, 7.16mmol), NIS (1.933g, 8.59mmol), Pd(OAc) were added to a 250mL reaction flask 2 (0.322g, 1.43mmol), AgCO 2 CF 3 (0.316g, 1.43mmol), 120mL 1,2-dichloroethane. The temperature was raised to 110°C and the reaction was stirred. Diatomaceous earth assisted filtration, and column chromatography gave 2.269 g of a yellow solid, with a yield of 81%. 1 HNMR (400MHz, CDCl 3 )δ8.05(d,J=1.1Hz,1H),7.01(d,J=7.8Hz,1H),6.59(dd,J=9.1,4.5Hz,2H),6.52(dd,J=12.6,4.8 Hz,2H),6.46(d,J=7.7Hz,1H),4.03(d,J=0.8Hz,3H),3.84–3.73(m,1H),3.46(t,J=10.6Hz,1H), 3.21–2.94(m,5H),2.87(m,1H); 13 C NMR (100MHz, CDCl 3 )δ153.5,143.8,140.7,139.6,138.8,135.0,134.3,133.5,133.2,132.9,130.0,128.6,110.1,62.2,39.98,35.0,34.7,33.1. HRMS: Calculated for C 18 h 19 INO[M+H] + 392.0506,found 392.0507.

Embodiment 2

[0049] Embodiment 2: the synthesis of compound 2

[0050]

[0051] Under nitrogen protection, compound 1 (200mg, 0.76mmol), NBS (163mg, 0.91mmol), Pd(OAc) were added to the 50mL reaction flask 2 (34mg, 0.15mmol), AgCO 2 CF 3 (34mg, 0.15mmol), 15mL 1,2-dichloroethane. The temperature was raised to 110°C and the reaction was stirred. Diatomaceous earth assisted filtration, and column chromatography gave 145 mg of white solid, yield 55%.

Embodiment 3

[0052] Embodiment 3: the synthesis of compound 3

[0053]

[0054] Compound 2 (1.200 g, 3.07 mmol), p-benzenemethanesulfonic acid monohydrate (1.168 g, 6.14 mmol), aqueous formaldehyde (4.6 mL, 61.40 mmol), 10 mL tetrahydrofuran and 1 mL water were added to a sealed 25 mL tube. The temperature was raised to 130° C., and the reaction was carried out for 72 hours. Cool to room temperature, add 10mL H 2 O, dichloromethane extraction, anhydrous Na 2 SO 4 Drying and column chromatography gave 1.046 g of a yellow solid with a yield of 94%. 1 H NMR (400MHz, CDCl 3 )δ9.79(s,1H),6.98(dd,J=7.9,1.8Hz,1H),6.68–6.56(m,3H),6.49(dd,J=7.9,1.8Hz,1H),6.38(dd ,J=7.9,1.8Hz,1H),3.88(m,1H),3.63–3.49(m,1H),3.25–3.15(m,3H),3.09–2.96(m,2H),2.81(m,1H ). 13 C NMR (100MHz, CDCl 3 )δ197.8,144.6,144.2,139.8,138.8,137.0,135.4,135.3,133.2,132.8,131.1,128.8,111.1,39.2,35.0,34.3,33.1. HRMS: Calculated for C 17 h 16 IO[M+H] + 363.0240,found 363.0244.

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Abstract

Design and synthesis of a class of NAD(P)H mimics with a chiral cycloarkanoquinoline skeleton: using optically pure cycloaryl alkanoxime ethers as starting materials, o-iodine can be obtained by carbon-hydrogen bond activation Cycloaryl alkanes aldoxime ethers, acid-promoted hydrolysis can give o-iodocycloaryl carboxaldehydes, followed by reduction methods to give o-iodocycloaranemethanols, followed by palladium-catalyzed coupling reactions with o-aminophenylboronic acids Or cross-coupling of boronic esters, and finally realize oxidative ring closure under oxidative conditions to obtain a class of NAD(P)H mimics with a chiral cycloaryl-alkanoquinoline skeleton. The present invention can effectively synthesize optically pure NAD(P)H mimics of the chiral ring alkane quinoline skeleton, and the NAD(P)H mimics of the chiral ring alkane quinoline skeleton can be synthesized under hydrogen Under certain conditions, it can be used as a recyclable chiral NAD(P)H mimic to realize C=N, asymmetric hydrogenation of aromatic heterocyclic compounds.

Description

technical field [0001] The invention relates to a class of NAD(P)H simulants with a chiral cycloarkanoquinoline skeleton and a synthesis method and application thereof, belonging to the field of organic synthesis and biomimetic asymmetric catalytic reduction. Background technique [0002] Biomimetic science is an ancient and young subject, which mainly studies the structure and working principle of living things. Based on these principles, new technologies and equipment have been developed to improve people's living standards and quality of life. In living organisms, nicotinamide adenine dinucleotide (NADH) and nicotinamide adenine dinucleotide phosphate (NADPH) are a very important class of coenzymes that play a crucial role in the transfer of protons and electrons . The process mainly depends on the interconversion between reduced NAD(P)H and oxidized NAD(P)+. NADPH is mainly produced in the pentose phosphate pathway and participates in the synthesis of nucleic acids an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/22B01J31/02C07D215/06C07D241/44
CPCB01J31/0244B01J2231/646C07B2200/07C07D215/06C07D221/22C07D241/44
Inventor 周永贵朱周豪王杰陈木旺孙蕾
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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