Reactions of 2-guanidino-1-cyclohexanol with ketals and acetals.
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概要
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Reactions of 2-guanidino-1-cyclohexanols (<B>1</B>, <B>1</B><I><SUB>d</SUB></I>, <B>1</B><I><SUB>l</SUB></I>) with 1,1-dimethoxycyclohexane in <I>N</I>,<I>N</I>-dimethylformamide in the presence of <I>p</I>-toluenesulfonic acid gave the <I>N</I>,<I>O</I>-cyclohexylidene derivatives (<B>5</B>, <B>5</B><I><SUB>d</SUB></I>, <B>5</B><I><SUB>l</SUB></I>), respectively. Similar reactions of <B>1</B><I><SUB>l</SUB></I> with 2,2-dimethoxypropane and with dimethyl acetals of <I>p</I>-tolualdehyde and <I>p</I>-bromobenzaldehyde also gave an <I>N</I>,<I>O</I>-isopropylindene, <I>N</I>,<I>O</I>-(<I>p</I>-methylbenzylidene) and <I>N</I>,<I>O</I>-(<I>p</I>-brornobenzylidene) derivative (<B>8</B><I><SUB>l</SUB></I>, <B>9</B><I><SUB>l</SUB></I>, <B>10</B><I><SUB>l</SUB></I>), respectively. From IR and PMR spectral studies of <B>9</B><I><SUB>l</SUB></I> <I>p</I>-toluenesulfonate, seven-membered structures as exemplified by <B>9A</B> were assigned. The <I>N</I>,<I>O</I>-blocked derivatives (<B>5</B>,<B>9</B>) are stable in weakly acidic or alkaline media, but in stronger media, they are cleaved to <B>1</B>. The usefulness of the protective groups was also examined. <B>9</B> was found to resist tosylation or mesylation in pyridine but not acylation. The numerical values of optical rotations of the guanidinocyclohexanols were greatly enhanced by <I>N</I>, <I>O</I>-blocking.
- 公益社団法人 日本化学会の論文
著者
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Tsuchiya Tsutomu
Institute of Bioorganic Chemistry
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Umezawa Sumio
Institute of Bioorganic Chemistry
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Takagi Yasushi
Institute of Bioorganic Chemistry
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Kawashima Osamu
Institute of Bioorganic Chemistry
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Sano Hiroshi
Institute of Bioorganic Chemistry
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