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√–‡∫’¬∫«‘∏’°“√»÷°…“ hydroboration-oxidation ‰¥â “√ D 147 ¡‘≈≈‘°√—¡
3
«‘∏’°“√‡μ√’¬¡ “√ D (65%) ¥—ß√Ÿª∑’Ë 3
“√ D ‡ªìπ “√∑’ˇªìπ‚§√ß √â“ßÀ≈—°¢Õß “√∑’Ë «‘∏’°“√‡μ√’¬¡ “√∑’ˇ°‘¥®“°ªØ‘°‘√‘¬“„πμ”√—∫¬“
‡°‘¥®“°ªØ‘°‘√‘¬“„πμ”√—∫¬“ª√– –‰æ≈∑—Èß 3 ™π‘¥ ª√– –‰æ≈ 3 ™π‘¥
°“√ —߇§√“–Àå®–„™â 4 ¢—ÈπμÕπ ¥—ßπ’È ªØ‘°‘√‘¬“·√° „π°“√»÷°…“§√—Èßπ’ȉ¥âπ”‡Õ“ªØ‘°‘√‘¬“ Steglich
6
§◊Õ°“√∑”ªØ‘°‘√‘¬“ aldol condensation √–À«à“ß 3,4- esterification ¡“„™â„π°“√‡μ√’¬¡ “√∑’ˇ°‘¥®“°
dimethoxybenzaldehyde °—∫ acetone „π¥à“ß ªØ‘°‘√‘¬“„πμ”√—∫¬“ª√– –‰æ≈∑—Èß 3 ™π‘¥ ‚¥¬‡ªìπ
‰¥â‡ªìπ “√ enone [5] ´÷ËßÀ¡Ÿà§’‚μπ®–∂Ÿ°‡ª≈’Ë¬π‰ª ªØ‘°‘√‘¬“∑’ˉ¡à„™â§«“¡√âÕπ º≈º≈‘μ¢Õߪؑ°‘√‘¬“¡’
‡ªìπÀ¡Ÿà·Õ≈°ÕŒÕ≈å ‚¥¬ NaBH ‰¥â‡ªìπ “√ alco- §«“¡·πàπÕπ°«à“«‘∏’ acid-catalyzed esterification
4
hol [6] ®“°π—Èπ “√ alcohol [6] ®–∂Ÿ°‡ª≈’Ë¬π‰ª‡ªìπ ‚¥¬ “√ D ®–∂Ÿ°π”¡“∑”ªØ‘°‘√‘¬“°—∫ linoleic acid,
diene [7] À√◊Õ “√ DMPBD ‚¥¬„™âªØ‘°‘√‘¬“ dehy- oleic acid ·≈– palmitic acid ‚¥¬¡’ “√ 4-dimethyl-
dration ¢—ÈπμÕπ ÿ¥∑⓬§◊Õ°“√‡μ‘¡À¡Ÿà‰Œ¥√Õ°´’ aminopyridine (DMAP) (1 equivalent) ·≈–
≈ßμ√ߪ≈“¬¢Õßæ—π∏–§Ÿà ´÷ËßμâÕßÕ“»—¬ªØ‘°‘√‘¬“ N,N(-dicyclohexyl-carbodiimide (DCC) (1.2
hydroboration ‚¥¬„™â 9-BBN ·≈–ÕÕ°´‘‰¥´å¥â«¬ equivalent) ‡ªìπ “√‡√àߪؑ°‘√‘¬“ ·≈–∑”ªØ‘°‘√‘¬“„π
H O „π¥à“ß ®–∑”„À≥⠓√ D À√◊Õ compound D dichloromethane ‡ªìπ‡«≈“ 24 ™—Ë«‚¡ß¿“¬„μâ
2 2
“√≈–≈“¬¢Õß DMPBD 221 ¡‘≈≈‘°√—¡ ∑”ªØ‘°‘√‘¬“ ∫√√¬“°“»¢Õß°ä“´‰π‚μ√‡®π∑’ËÕÿ≥À¿Ÿ¡‘ÀâÕß
√Ÿª∑’Ë 3 °√–∫«π°“√ —߇§√“–Àå “√ D