乙基(2E)-3-(2,3-二氢-1-苯并呋喃-5-基)丙烯酸酯合成路线 （共 12 条）
反应条件
sodium hydrogencarbonate; acetic acid in methanol; water; toluene
参考文献
Takeda Chemical Industries, Ltd.
Patent: US6348485 B1, 2002 ;
反应条件
1: ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate With N-benzyl-trimethylammonium hydroxide in tetrahydrofuran; methanol T=-78°C; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; 2: 2,3-dihydrobenzo[b]furan-5-carboxaldehyde in tetrahydrofuran; methanol T=-78°C; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Overall yield = 78 percent; diastereoselective reaction;
参考文献
Phytochemistry, , vol. 96, p. 132 - 147
反应条件
1.1: 92 percent / TiCl4 / CH2Cl2 / 1 h 2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 2.2: 88 percent / tetrahydrofuran / 1 h / 20 °C View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 45, # 19 p. 4222 - 4239
反应条件
Condensation; Wittig olefination;
参考文献
Coleman, Paul J.; Hutchinson, John H.; Hunt, Cecilia A.; Lu, Ping; Delaporte, Enock; Rushmore, Tom
Tetrahedron Letters, 2000 , vol. 41, # 31 p. 5803 - 5806
反应条件
1.1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 2.1: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 3.1: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 4.1: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 5.1: SOCl2 / 75 °C 6.1: AlCl3 / 1,2-dichloro-ethane / 20 °C 7.1: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C 8.1: NaH / tetrahydrofuran / 20 °C 8.2: 60 percent / tetrahydrofuran / 20 °C 9.1: 81 percent / H2; ethanolic NH3 / Raney-nickel / 40 °C / 3600.36 Torr View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 2: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 3: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 4: 93 percent / aq. KOH / ethanol / 1 h / 90 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 2: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 3: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 4: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 5: SOCl2 / 75 °C 6: AlCl3 / 1,2-dichloro-ethane / 20 °C View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 45, # 19 p. 4222 - 4239
反应条件
1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 2: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 3: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C 4: 93 percent / aq. KOH / ethanol / 1 h / 90 °C 5: SOCl2 / 75 °C 6: AlCl3 / 1,2-dichloro-ethane / 20 °C 7: 89 percent / AcOH; H2 / 10percent Pd/C/H2O / 1 h / 20 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
反应条件
hydrogen; palladium on activated carbon in acetic acid T=50°C; P=1470.15 - 2205.22 Torr; 1 h;
参考文献
Takeda Pharmaceutical Company Limited
Patent: EP1792899 A1, 2007 ;
Location in patent: Page/Page column 11-12 ;
反应条件
1: 99 percent / H2 / 10percent Pd/C/H2O / ethanol / 2 h / 20 °C 2: 97 percent / NaOAc; AcOH; Br2 / 1 h / 20 °C 3: 53 percent / AcOH; Fe; Br2 / 5 h / 50 °C View Scheme
参考文献
Uchikawa, Osamu; Fukatsu, Kohji; Tokunoh, Ryosuke; Kawada, Mitsuru; Matsumoto, Kiyoharu; Imai, Yumi; Hinuma, Shuji; Kato, Koki; Nishikawa, Hisao; Hirai, Keisuke; Miyamoto, Masaomi; Ohkawa, Shigenori
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4222 - 4239
