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[1]黄翔,黄强,周巍,等.1-(4′-乙炔基苯基)-4-正丙基-2,6,7-三氧杂双环［2.2.2］辛烷的合成[J].武汉工程大学学报,2011,(05):15-17.[doi:10.3969/j.issn.16742869.2011.05.005]
　HUANG Xiang,HUANG Qiang,ZHOU Wei,et al.Synthesis of 1-(4′-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo［2.2.2］octane[J].Journal of Wuhan Institute of Technology,2011,(05):15-17.[doi:10.3969/j.issn.16742869.2011.05.005]
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1-(4′-乙炔基苯基)-4-正丙基-2,6,7-三氧杂双环［2.2.2］
辛烷的合成(/HTML)
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《武汉工程大学学报》[ISSN:1674-2869/CN:42-1779/TQ]

卷:
期数:
2011年05期
页码:
15-17
栏目:
化学与化学工程
出版日期:
2011-05-31

文章信息/Info

Title:
Synthesis of 1-(4′-ethynylphenyl)-4-n-propyl-2,6,7-trioxabicyclo
［2.2.2］octane
文章编号:
16742869(2011)05001503
作者:
黄翔; 黄强; 周巍; 巨修练*
武汉工程大学化工与制药学院，绿色化工过程教育部重点实验室，
湖北省新型反应器与绿色化学工艺重点实验室，湖北 武汉 430074
Author(s):
HUANG Xiang;  HUANG Qiang;  ZHOU Wei;  JU Xiulian
Key Laboratory for Green Chemical Process of Ministry of Education,
Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology,
School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430074,China
关键词:
三氧杂双环辛烷; GABA受体; 非竞争性拮抗剂; 合成
Keywords:
trioxabicyclooctane;  GABA receptor; noncompetitive antagonist; synthesis
分类号:
TQ265.1
DOI:
10.3969/j.issn.16742869.2011.05.005
文献标志码:
A
摘要:
以正戊醛为原料经Cannizzaro反应，脱水，酯化，合环和引入炔基5步反应，总收率为5%，成功合成了1(4′乙炔基苯基)4正丙基2,6,7三氧杂双环［2.2.2］辛烷. 目标化合物的熔点及1H NMR谱, MS与文献报道一致.
Abstract:
1(4′ethynylphenyl)4npropyl2,6,7trioxabicyclo［2.2.2］octane (EBOB) was successfully synthesized from nvaleraldehyde as a starting material via Cannizzaro reaction, dehydration, esteration, cyclization and introducing the ethynyl group. The overall yield of it in five steps from nvaleraldehyde was 5%. The melting point, 1H NMR and MS spectra are consistent with the literature values.

参考文献/References:

［1］Cole L M, Casida J E. GABAgated chloride channel: Binding site 4′ethynyl4n［2,33H2］ propylbicycloorthobenzoate (［3H］EBOB) in vertebrate brain and insect head［J］. Pestic Biochem Physiol， 1992, 44: 18.
［2］Squires R F, Casida J E, Richardson M, Saederup E. ［35S］ tButylbicyclophosphorothionate binds with high afnity to brainspecific sites coupled to aminobutyric acidA and ion recognition sites［J］. Mol pharmacol， 1983, 23: 326336.
［3］Plamer J C, Cole L M, Larkin, P J, et al. 1(4Ethynylphenyl)4substituted2,6,7trioxabicyclo［2.2.2］ octanes: Effects of 4substituent on toxicity to houseflies and mice and potency at the GABAgated chloride channel［J］. J Agric Food Chem， 1991, 39: 13291334.
［4］Plamer J C, Cole L M, Larkin P J, et al. 1(4ethynylphenyl)2,6,7trioxabicyclo［2.2.2］ octanes: Structural featuresand mechanismsof proinsecticidalactionand selective toxicit［J］. Agric Food Chem， 1991, 39:1335.
［5］Corey J E, Raju N. A new general synthetic route to bridged carboxylic ortho esters［J］. Tetrahedron Lett， 1983, 24: 55715574.
［6］Plamer J C, Casida J E. 1,4Disubstituted 2,6,7trioxabicyclo［2.2.2］ octanes: A new class of insecticides［J］. J Agric Food Chem， 1985, 33: 976.
［7］Plamer J C, Casida J E. 1(4Ethynylphenyl)2,6,7trioxabicylo［2.2.2］ octanes: A new order of potency for insecticides acting at the GABA gated chloride channel［J］. J Agric Food Chem， 1989, 37: 213.
［8］Cole L M, Casida J E. Selective catalytic hydrogenation of an olefin moiety in the presence of a terminal alkyne function［J］. Tetrahedron Lett， 1990, 31: 2857.

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备注/Memo

备注/Memo:
收稿日期：20110323作者简介：黄翔（1985 ），男，汉族，湖北宜昌人，硕士研究生.研究方向：杂环化合物的合成.指导老师：巨修练，教授，博士，博士研究生导师.研究方向：新型农药的研发与合成.*
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