Synthesis of substituted tetrahydronaphthalene

FU Bing-yue; TANG Hui; ZHENG Can-hui; LIU Jia; ZHOU Feng; ZHOU You-jun; ZHU Ju; LV Jia-guo

doi:10.3969/j.issn.1006-0111.2012.01.009

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Objective To optimize the synthesis of substituted tetrahydronaphthalene and investigate the influence of 10% Pd/C catalyst in the synthesis of key intermediate. Methods A parallel test was carried out to compare the catalytic activity of triethyl silicane and the 10% Pd/C catalyst, including the total analysis of experimental result . And orthogonal experimental design was used and the influence of solvent and reactant ratio on the yield were investigated. Results The cost of the 10% Pd/C catalyst was obviously lower than that of triethyl silicane,with high yield, little impurity easy effluent disposal. Orthogonal test confirms that the ratio of reactant and catalystthe was the most significant factor. Conclusion The experiments proved that the optimal preparation procedure was much more available for industrial production using the 10% Pd/C as a catalyst.

Synthesis of substituted tetrahydronaphthalene

1. Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

2. Provincial Hospital Affiliated to Shandong University, Jinan 250021, China

Received Date: 2011-01-20

Rev Recd Date: 2011-09-29

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Abstract: Objective To optimize the synthesis of substituted tetrahydronaphthalene and investigate the influence of 10% Pd/C catalyst in the synthesis of key intermediate. Methods A parallel test was carried out to compare the catalytic activity of triethyl silicane and the 10% Pd/C catalyst, including the total analysis of experimental result . And orthogonal experimental design was used and the influence of solvent and reactant ratio on the yield were investigated. Results The cost of the 10% Pd/C catalyst was obviously lower than that of triethyl silicane,with high yield, little impurity easy effluent disposal. Orthogonal test confirms that the ratio of reactant and catalystthe was the most significant factor. Conclusion The experiments proved that the optimal preparation procedure was much more available for industrial production using the 10% Pd/C as a catalyst.

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Reference (6)

[1]	周有骏,姚斌,朱驹. 具有抗真菌活性的N-取代-2-氨基-1 ,2 ,3 ,4-四氢萘化合物及其盐类:中国, 1817851A[P]. 20062102241.
[2]	Paull KD, Zee-Cheng RK, Cheng CC. Some substituted naphthazarins as potential anticancer agents[J]. J Med Chem, 1976, 19(2):337.
[3]	Hamdy NA, Gamal-Eldeen AM, Abdel-Aziz HA, et al. Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives[J]. Eur J Med Chem, 2010, 45(2):463.
[4]	Varella MH, de Mello FG, Linden R. Evidence for an antiapoptotic role of dopamine in developing retinal tissue[J]. J Neurochem, 1999, 73(2):485.
[5]	Tang H, Zhou YJ, Li YW, et al. Design, synthesis and antifungal activities in vitro of novel tetralin compounds[J].Chinese Chemical Letters, 2008, 19(3): 264.
[6]	Norlander JE, Payne MJ, Njoroge FG, et al. A short enantiospecific synthesis of 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN) [J] . J Org Chem,1985, 50, 3619.

[1]	周有骏,姚斌,朱驹. 具有抗真菌活性的N-取代-2-氨基-1 ,2 ,3 ,4-四氢萘化合物及其盐类:中国, 1817851A[P]. 20062102241.
[2]	Paull KD, Zee-Cheng RK, Cheng CC. Some substituted naphthazarins as potential anticancer agents[J]. J Med Chem, 1976, 19(2):337.
[3]	Hamdy NA, Gamal-Eldeen AM, Abdel-Aziz HA, et al. Modulation of carcinogen metabolizing enzymes by new fused heterocycles pendant to 5,6,7,8-tetrahydronaphthalene derivatives[J]. Eur J Med Chem, 2010, 45(2):463.
[4]	Varella MH, de Mello FG, Linden R. Evidence for an antiapoptotic role of dopamine in developing retinal tissue[J]. J Neurochem, 1999, 73(2):485.
[5]	Tang H, Zhou YJ, Li YW, et al. Design, synthesis and antifungal activities in vitro of novel tetralin compounds[J].Chinese Chemical Letters, 2008, 19(3): 264.
[6]	Norlander JE, Payne MJ, Njoroge FG, et al. A short enantiospecific synthesis of 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN) [J] . J Org Chem,1985, 50, 3619.

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Synthesis of substituted tetrahydronaphthalene

doi: 10.3969/j.issn.1006-0111.2012.01.009

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通讯作者: 陈斌, [email protected]

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