Preparation method of olefin and method for synthesizing chondriamidea and chondriamidec
An olefin and hydrocarbon-based technology, which is applied in the preparation of organic compounds, the preparation of amino compounds from amines, and the preparation of carbon-based compounds. It can solve the problems of high reaction temperature and environmental pollution, and achieve simple operation, cost reduction, and high-efficiency catalytic conversion. Effect
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[0045] The invention provides a kind of preparation method of olefin, comprising:
[0046] Mixing a compound of formula (I), a palladium catalyst, a phosphorus ligand, a base, and an organic solvent for light reaction at room temperature, to obtain an alkene having a structure of formula (II);
[0047]
[0048] Among them, R 1 C1-C50 alkyl group, C1-C50 heteroatom-containing alkyl group, C2-C50 unsaturated hydrocarbon group, C2-C50 heteroatom-containing unsaturated hydrocarbon group or C3-C50 aromatic group;
[0049] X is a hydrogen atom, methylene, oxygen or nitrogen;
[0050] When X is a hydrogen atom, R 2 group does not exist;
[0051] When X is methylene, oxygen or nitrogen, R 2 C1-C50 alkyl group, C1-C50 heteroatom-containing alkyl group, C2-C50 unsaturated hydrocarbon group, C2-C50 heteroatom-containing unsaturated hydrocarbon group, C3-C50 aromatic group or X and R 2 Form a five- or six-membered ring;
[0052] or R 1, X and their carbons form a ring;
[0053...
Embodiment 1
[0081] Embodiment 1, preparation 1-pentadecene
[0082] Reaction formula:
[0083]
[0084] The specific method is as follows:
[0085]Add photocatalyst palladium chloride (2mol%, 0.7mg), 4,5-bis-diphenyl Phosphine-9,9-dimethylxanthene (L1) (3mol%, 3.5mg), 2-(dicyclohexylphosphino)biphenyl (L2) (4mol%, 2.8mg) and active aliphatic NHPI Ester (0.2 mmol, 80.2 mg). The air in the tube was completely replaced with argon three times, and then 2,4,6-collidine (0.2 mmol, 24.2 mg) and 2 mL of N,N-dimethylacetamide (DMA) were added under argon atmosphere. The reaction system was continuously stirred at room temperature for 15 hours under the irradiation of a 36W blue LED lamp (IKA magnetic stirrer, RCT basic type, stirring speed 500 rpm). After the reaction is complete, use H 2 The reaction was quenched with O, and the reaction solution was extracted with ethyl acetate (3*10 mL), and then the combined organic phase was concentrated by rotary evaporation (BUCHI Co., Ltd., BUCHI r...
Embodiment 2
[0089] Embodiment 2, preparation Z-heptadeca-1,8-diene
[0090] Reaction formula:
[0091]
[0092] Method is with example 1, and productive rate sees figure 1 .
[0093] Utilize NMR to analyze the Z-heptadeca-1,8-diene obtained in embodiment 2, obtain the result:
[0094] 1 H NMR (400MHz, CD2Cl2) δ5.81 (ddt, J = 16.9, 10.2, 6.7Hz, 1H), 5.38–5.33 (m, 2H), 5.04–4.90 (m, 2H), 2.08–1.98 (m, 6H ),1.41–1.25(m,18H),0.88(t,J=6.9Hz,3H).
[0095] 13 C NMR(101MHz,CD2Cl2)δ139.2,130.0,129.8,114.2,33.8,31.9,29.8,29.6,29.5,29.3,28.9,28.8,27.2,27.1,22.7,14.1.(one carbon signal is overlapped)
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