Probes for narcotic receptor mediated phenomena.: Part 31:: Synthesis of rac-(3R,6aS,11aS)-2-methyl-1,3,4,5,6,11a-hexahydro-2H-3,6a-methanobenzofuro[2,3-c]azocine-10-ol, and azocine-8-ol, the ortho-c and the para-c oxide-bridged phenylmorphan isomers
Probes for narcotic receptor mediated phenomena.: Part 31:: Synthesis of rac-(3R,6aS,11aS)-2-methyl-1,3,4,5,6,11a-hexahydro-2H-3,6a-methanobenzofuro[2,3-c]azocine-10-ol, and azocine-8-ol, the ortho-c and the para-c oxide-bridged phenylmorphan isomers
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DOI：
10.1016/s0040-4020(03)00659-8
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发表时间：
2003-06-16
期刊：
影响因子：
2.1
通讯作者：
Rice, KC
中科院分区：
文献类型：
--
作者：
Tadic, D;Linders, JTM;Rice, KC
合成了12种可能的氧化物桥连苯基吗啉中的两种，外消旋-（3R，6aS，11 aS）-2-甲基-1，3，4，5，6，11 a-六氢2 H-3，6a-亚甲基苯并呋喃并[2，3-c]吖辛因-10-醇（7）（邻位-c化合物）和rac-（3R，6aS，11 aS）-2-甲基-1，3，4，5，6，11 a-六氢-2H-3，6a-亚甲基苯并呋喃并[2，3-c]吖辛因-8-醇（8）（对位-c化合物）。单晶X-射线衍射研究表明，在两个7（.）CHCl（3）和8（.）HBr为6.9度。两种化合物的C-12-C-6a-C-6 b-C-10a扭转角均为139.3 °。在与特定的阿片受体相互作用的苯吗啡类化合物中，作为激动剂或拮抗剂的酚环和哌啶环之间的角度关系具有相当大的理论意义。(C)2003爱思唯尔科技有限公司版权所有。
Two of the 12 possible oxide-bridged phenylmorphans, were synthesized, rac-(3R,6aS,11aS)-2-methyl-1,3,4,5,6,11a-hexahydro2H-3,6a-methanobenzofuro[2,3-c]azocine-10-ol (7) (the ortho-c compound), and rac-(3R,6aS, 11aS)-2-methyl-1,3,4,5,6,11a-hexahydro-2H-3,6a-methanobenzofuro[2,3-c]azocine-8-ol (8) (the para-c compound). Single-crystal X-ray diffraction studies indicated that the dihedral angle between the least squares planes through the phenyl ring and the atoms C-1, C-11a, C-12, and C-3 in the piperidine ring in both 7(.)CHCl(3) and 8(.)HBr was 6.9degrees. The C-12-C-6a-C-6b-C-10a torsion angle was found to be 139.3degrees for both compounds. The angular relationship between the phenolic ring and the piperidine ring in phenylmorphans that interact with specific opioid receptors as agonists or antagonists is of considerable theoretical interest. (C) 2003 Elsevier Science Ltd. All rights reserved.