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Furan 4alpha-methylol polyhydro naphthalene compound and its synthesis and use

A synthesis method and compound technology, applied in steroids, organic chemistry, etc., can solve problems such as failure to obtain target products, severe ozonation reaction conditions, and functional group effects.

Inactive Publication Date: 2005-11-30
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, in the process of synthesizing (±) spiniferin-1 and its analogues, the target product could not be obtained when using the same strategy. The main problem is that the ozonation reaction conditions are too severe, which has an impact on the functional groups in other parts of the molecule.

Method used

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  • Furan 4alpha-methylol polyhydro naphthalene compound and its synthesis and use
  • Furan 4alpha-methylol polyhydro naphthalene compound and its synthesis and use
  • Furan 4alpha-methylol polyhydro naphthalene compound and its synthesis and use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The synthesis of embodiment 1 compound 2a

[0069]

[0070] 0.26ml (2mmol) of diisopropylamine was dissolved in 1ml of tetrahydrofuran, cooled to -78°C, and 1.0ml of 2M (2mmol) n-BuLi was added dropwise. Stir for 15 minutes after addition.

[0071] A solution of 220 mg (1 mmol) of compound 1a in 2 ml of tetrahydrofuran was slowly added dropwise thereto at -78°C. After stirring the reaction at -78°C for 2 hours, add 2mmol (2eq) ZnCl 2 , stirred for 5min, added 2mmol (2eq) THPOCH 2 CHO was added and reacted for 1 hour. saturated NH 4 Cl solution quenched the reaction. Dichloromethane extraction. Combine the organic phases, wash with water, wash with saturated NaCl solution, Na 2 SO 4 dry. The solvent was removed, and 320 mg of compound 2a was obtained by passing through the column (90% yield).

[0072] Compound 2a: C20H30O6 (366.45)

[0073] 1 H-NMR (CDCl 3 , 300MHz): δ5.94 (m, 1H), 4.61 (m, 1H), 3.5-4.3 (m, 8H), 1.3-1.8 (m, 17H) 1.28 (m, ...

Embodiment 2

[0074] The synthesis of embodiment 2 compound 3a

[0075]

[0076] 200mg (0.8mmol) of compound 2a was dissolved in 4ml of THF, 20mg of p-toluenesulfonic acid was added, and stirred at 60°C for 3hr. The solvent was removed, and the residue was columned to obtain 130 mg (77%) of colorless oil 3a.

[0077] Compound 3a: C15H18O3 (246.30)

[0078] 1 H-NMR (CDCl 3 300MHz): δ7.17(d, 1H, J=1.8Hz), 6.24(s, 1H), 6.19(d, 1H, J=1.8Hz), 4.0-4.2(m, 2H), 3.20(d, 1H , J=16.5Hz), 2.59(d, 1H, J=16.2Hz), ), 1.3-2.5(m, 8H), 1.19(t, 3H, J=7.2Hz).

Embodiment 3

[0079] The synthesis of embodiment 3 compound 4a

[0080]

[0081] 100 mg (0.4 mmol) of compound 3a were dissolved in 2 ml THF. Add 40mg (2.5eq) LiAlH dropwise at room temperature 4 In 5ml THF suspension, react for 0.5hr. A small amount of water was used to quench the reaction, filtered, the solvent was evaporated, and the residue was separated by column chromatography to obtain 88 mg of compound 4a (100%).

[0082] Compound 4a: C13H16O2 (204.26)

[0083] m.p.92-93℃

[0084] 1 H-NMR (CDCl 3 300MHz) δ7.17(d, 1H, J=1.8Hz), 6.19(d, 1H, J=1.8Hz), 6.15(d, 1H, J=0.9Hz), 3.46(m, 2H), 2.89(d , 1H, J=16.8Hz), 2.36(d, 1H, J=16.5Hz), ), 1.2-2.3(m, 8H).

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Abstract

The present invention is furan 4a-methylol polyhydro naphthalene compound and its synthesis and use. The structure expression is given. The present invention has simple synthesis process suitable for industrial production and may be used in synthesizing marine naturla produce (minus or plus) spiniferin-1 and its analog.

Description

technical field [0001] The invention relates to various furo-4a hydroxymethyl polyhydronaphthalene compounds, a synthesis method and applications thereof. This type of compound can be synthesized under acid catalyzed conditions and by carbocation rearrangement reaction method induced by fluorosulfonyl fluoride (see CN 97106576.4). The above compound can efficiently synthesize the marine natural product spiniferin-1 and its analogues. Background technique [0002] Natural spiniferin-1 is a furan sesquiterpene (Tetra.Lett.1975(45), 3727) isolated from a sponge organism pleraplysilla in the Bay of Naples by Italian professor G.Cimino. In 1980, the J.A.Marshall group determined its structure by synthesizing the dihydro derivative (±)dihydrospiniferin-1 of spiniferin-1 as follows (see J.Amer.Chem.Soc.1980(102), 4274): [0003] [0004] (±)spiniferin-1 (±)dihydrospiniferin-1 [0005] It is well known that there are a large number of natural products containing benzofuran st...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/91C07D307/94C07J71/00
Inventor 田伟生丁凯
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI