Synthesis and conformational studies of 9-benzyloxy-18-substituted [3.3]metacyclophanes
Synthesis and conformational studies of 9-benzyloxy-18-substituted [3.3]metacyclophanes
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9-苄氧基-18-取代的[3.3]间环芳烷的合成和构象研究
DOI：
10.1139/cjc-2015-0174
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发表时间：
2015
影响因子：
1.1
通讯作者：
T. Yamato
中科院分区：
文献类型：
--
作者：
Md. Monarul Islam;Tomiyasu Hirotsugu;Taisuke Matsumoto;J. Tanaka;T. Yamato
通过改进的TosMIC偶联反应，经酸处理和Wolff-Kishner还原，合成了一系列含内取代苯氧基的Synn-[3.3]偏环芳烃(MCPs)。由甲氧基[3.3]MCPs与BBr3在室温下脱甲基化得到相应的羟基[3.3]MCPs，再经O-苄基化反应合成了反一元和二苯甲氧基[3.3]MCPs。当syn-6，15-di-tert-butyl-9-methoxy-18-methyl[3.3]MCP-2，11-dione被TMSI处理后，通过亲核的分子内环化反应形成二氢苯并呋喃环，得到了一个有趣而有趣的结果。通过对6a的~1H核磁共振和X-射线分析，确定其在溶液和固体中均为SYN构象。
A series of syn-[3.3]metacyclophanes (MCPs) containing internal substituted benzyloxy group have been synthesized by the modified TosMIC coupling reaction followed by acid treatment and Wolff–Kishner reduction. anti-Mono- and di-benzyloxy[3.3]MCPs are synthesized by O-benzylation of the corresponding hydroxy[3.3]MCPs, which are obtained by demethylation of methoxy[3.3]MCPs with BBr3 at room temperature. An interesting and intriguing result was obtained when syn-6,15-di-tert-butyl-9-methoxy-18-methyl[3.3]MCP-2,11-dione was treated with TMSI to afford the formation of a dihydrobenzofuran ring by a nucleophilic intramolecular cyclization reaction. The 1H NMR and X-ray analysis of 6a confirms that it adopts a syn (chair–chair) conformation in both solution and solid state.
用 BBr3 对 5,n-二叔丁基-8,n-二甲氧基[2.n]间环芬-1-炔进行脱甲基化，得到新型[n]苯并呋喃芬
影响因子：
3.8
作者：
Akther T
通讯作者：
Akther T