1-溴-8-(四氢吡喃氧基)辛烷合成路线 （共 69 条）
反应条件
1: 1) Mg, 2) Li2CuCl4 / 1) THF, 2) THF, a) -70 deg C to 20 deg C over 45 min, b) 2 h at 20 deg C
2: 92 percent / TsOH*Py / methanol / 3 h / 45 °C
3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / 20 °C
View Scheme
参考文献
Cheskis, B. A.; Ivanova, N. M.; Moiseenkov, A. M.; Nefedov, O. M.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990 , vol. 39, # 11 p. 2296 - 2300
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990 , # 11 p. 2539 - 2544
反应条件
1.1: n-butyllithium / tetrahydrofuran
1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C
2.1: lithium; ethylamine / 1 h / -5 °C
3.1: p-toluenesulfonic acid / ethanol / 3 h / Heating
4.1: iodine; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 1 h / 0 °C
5.1: n-butyllithium / tetrahydrofuran
5.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C
6.1: lithium; ethylamine / 1 h / -5 °C
7.1: p-toluenesulfonic acid / ethanol / 3 h / Heating
8.1: 93 percent / pyridine / 0.5 h / 20 °C
View Scheme
参考文献
Naka, Hideshi; Nakazawa, Tomotake; Sugie, Mieko; Yamamoto, Masanobu; Horie, Yoshiteru; Wakasugi, Ryohei; Arita, Yutaka; Sugie, Hajime; Tsuchida, Koji; Ando, Tetsu
Bioscience, Biotechnology and Biochemistry, 2006 , vol. 70, # 2 p. 508 - 516
反应条件
1: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h
2: p-TsOH / methanol / 2 h / Heating
View Scheme
参考文献
Rossi, Renzo; Carpita, Adriano; Gaudenzi, Loretta; Quirici, Maria Grazia
Gazzetta Chimica Italiana, 1980 , vol. 110, # 4 p. 237 - 246
反应条件
1: 91 percent / NaI / acetone
2: 1.) (i-C3H7)2NLi / 1.) THF, n-hexane, room temp., 3 h, 2.) 55 deg C, 12 h
3: 92 percent / Amberlyst H-15 / methanol / 1 h / 45 °C
4: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating
5: MnO2 / CH2Cl2 / 6 h / Ambient temperature
View Scheme
参考文献
Cardillo, Giuliana; Orena, Mario; Porzi, Gianni; Sandri, Sergio
Gazzetta Chimica Italiana, 1980 , vol. 110, # 9/10 p. 523 - 526
反应条件
1: 1.) Li2CuCl4, 2.) PTSA / 1.) THF, room temperature, 12 h, 2.) CH3OH, room temperature, 6 h
2: pyridine / CH2Cl2 / 12 h / Ambient temperature
View Scheme
参考文献
Nakashima, Hideki; Hirata, Norihiko; Iwamura, Takeru; Yamagiwa, Yoshiro; Kamikawa, Tadao
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 19 p. 2849 - 2858
反应条件
sodium iodide in acetone
参考文献
Al Dulayymi, Juma'a R.; Baird, Mark S.; Roberts, Evan; Deysel, Madrey; Verschoor, Jan
Tetrahedron, 2007 , vol. 63, # 12 p. 2571 - 2592
反应条件
1.1: n-butyllithium / tetrahydrofuran
1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C
2.1: lithium; ethylamine / 1 h / -5 °C
View Scheme
参考文献
Naka, Hideshi; Nakazawa, Tomotake; Sugie, Mieko; Yamamoto, Masanobu; Horie, Yoshiteru; Wakasugi, Ryohei; Arita, Yutaka; Sugie, Hajime; Tsuchida, Koji; Ando, Tetsu
Bioscience, Biotechnology and Biochemistry, 2006 , vol. 70, # 2 p. 508 - 516
反应条件
1: 91 percent / NaI / acetone
2: 1.) (i-C3H7)2NLi / 1.) THF, n-hexane, room temp., 3 h, 2.) 55 deg C, 12 h
3: 92 percent / Amberlyst H-15 / methanol / 1 h / 45 °C
4: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating
View Scheme
参考文献
Cardillo, Giuliana; Orena, Mario; Porzi, Gianni; Sandri, Sergio
Gazzetta Chimica Italiana, 1980 , vol. 110, # 9/10 p. 523 - 526
反应条件
1: 40 percent
3: 2) NH4Cl, H2O / 1) THF -78 deg C, 2) r.t.
4: 62 percent / oxalylchloride, triethylamine, DMSO / CH2Cl2 / -60 °C
5: 52 percent / NaH / tetrahydrofuran / Ambient temperature
6: Jones' oxidation
View Scheme
参考文献
Altenbach, Hans-Josef; Holzapfel, Winfried; Smerat, Gerd; Finkler, Stefan H.
Tetrahedron Letters, 1985 , vol. 26, # 51 p. 6329 - 6332
