十八碳-9,12-二炔酸合成路线 （共 19 条）
反应条件
1: KI / acetone; H2O / Heating
2: (i) NaOEt, (ii) KOH, MeOH, H2O
3: (i) EtMgBr, THF, (ii) CuCN, /BRN= 1744118/
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参考文献
de Gaudemaris,M.; Arnaud,P.
Bulletin de la Societe Chimique de France, 1962 , p. 315 - 325
反应条件
tetrahydrofuran; ethylmagnesium bromide
anschliessenden Erwaermen des Reaktionsgemisches mit 1-Brom-oct-2-in und Kupfer(I)-cyanid;
参考文献
Osbond; Wickens
Chemistry and Industry (London, United Kingdom), 1959 , p. 1288
Journal of the Chemical Society, 1961 , p. 2779,2786
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Osbond et al.
Journal of the Chemical Society, 1961 , p. 2779,2783
反应条件
1: diethyl ether
2: acetone; sodium iodide
3: ethanol / Behandeln des Reaktionsgemisches mit wss.-methanol.Kalilauge und Erhitzen des nach dem Ansaeuern erhaltenen Reaktionsprodukts unter 0.0001 Torr auf 140grad
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参考文献
Raphael; Sondheimer
Journal of the Chemical Society, 1950 , p. 2100
反应条件
1: (i) Na, liq. NH3, (ii) /BRN= 1756104/, ether
2: (i) EtMgBr, THF, (ii) CuCN, (iii) /BRN= 1744118/
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参考文献
Kraevskii,A.A. et al.
Zhurnal Organicheskoi Khimii, 1965 , vol. 1, p. 44 - 46,42 - 44
反应条件
1: (i) NaOEt, (ii) KOH, MeOH, H2O
2: (i) EtMgBr, THF, (ii) CuCN, /BRN= 1744118/
View Scheme
参考文献
de Gaudemaris,M.; Arnaud,P.
Bulletin de la Societe Chimique de France, 1962 , p. 315 - 325
反应条件
1: 95 percent / diethyl ether / 0 °C
2: 53 percent / NaBD4, 2-methylbut-2-ene, BF3*OEt2 / bis-(2-methoxy-ethyl) ether / 1) 0 deg C, 30 min, 2) RT, 2h
3: 70 percent / KOH / ethanol; H2O / 1.5 h / Heating
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参考文献
Crombie, Leslie; Morgan, David O.; Smith, Elisabeth H.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 3 p. 567 - 575
反应条件
1: 82 percent
2: 1.) sodium borotritide, sodium borohydride, 2-methylbut-2-ene, boron trifluoride-diethyl ether; 3.) tritiated acetic acid / 1.) diglyme, 2 h, 0 deg C; 2.) diglyme, 30 min, 0 deg C -> r.t, 2 h; 3.) 20 deg C, overnight
3: potassium hydroxyde / ethanol / Heating
View Scheme
参考文献
Crombie, Leslie; Holloway, Stephen J.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985 , p. 2425 - 2434
反应条件
in diethyl ether
T=0°C;
参考文献
Crombie, Leslie; Morgan, David O.; Smith, Elisabeth H.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 3 p. 567 - 575
参考文献
Bascetta, Emanuele; Gunstone, Frank D.; Walton, John C.
Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983 , p. 603 - 614
