• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】37700

【品名】7-ethylbicyclo[3.3.1]non-6-en-3-one

【CA登记号】

【 分 子 式 】C11H16O

【 分 子 量 】164.24744

【元素组成】C 80.44% H 9.82% O 9.74%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Condensation of diketone (I) with the organocerium reagent derived from ethylmagnesium bromide and CeCl3 afforded the oxaadamantanol (II), which was further converted to mesylate (III) upon reaction with methanesulfonyl chloride and Et3N. Subsequent fragmentation of (III) by treatment with silica gel in CH2Cl2 produced bicyclic enone (IV). This was condensed with 2-amino-4-methylbenzonitrile (V) in the presence of AlCl3 in refluxing 1,2-dichloroethane to furnish the target tetracyclic derivative. Resolution was then achieved by chiral MPLC.

1 Tetrahedron 1996, 51, 16, 5867-80.
2 El Achad, R.; Görbig, D.M.; Camps, P.; et al.; Synthesis, in vitro pharmacology, and molecular modeling of very potent tacrine - Huperzine A hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of Alzheimer's disease. J Med Chem 1999, 42, 17, 3227.
3 Contreras Lascorz, J.; El Achab, R.; Camps Garcia, P.; Baños Diez, J.E.; Muñoz-Torrero Lopez-Ibarra, D.; Badia Sancho, A.; Morral Cardoner, J.; Simon Fornell, M.; Görbig Romeu, M.; Vivas, N.M. (Medichem SA); Polycyclic aminopyridine cpds. which are acetylcholinesterase inhibitors, process for preparing them and their use. EP 0796849; ES 2100129; US 5965569; WO 9713754 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 37697 bicyclo[3.3.1]nonane-3,7-dione C9H12O2 详情 详情
(II) 37698 3-ethyl-2-oxatricyclo[3.3.1.1(3,7)]decan-1-ol C11H18O2 详情 详情
(III) 37699 3-ethyl-2-oxatricyclo[3.3.1.1(3,7)]dec-1-yl methanesulfonate C12H20O4S 详情 详情
(IV) 37700 7-ethylbicyclo[3.3.1]non-6-en-3-one C11H16O 详情 详情
(V) 37701 2-amino-4-methylbenzonitrile 26830-96-6 C8H8N2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

Condensation of diketone (I) with the organocerium reagent derived from methylmagnesium bromide and CeCl3 afforded the oxaadamantanol (II), which was further converted to mesylate (III) upon reaction with methanesulfonyl chloride and Et3N. Subsequent fragmentation of (III) by treatment with silica gel in CH2Cl2 produced bicyclic enone (IV). This was condensed with 2-amino-4-fluorobenzonitrile (V) in the presence of AlCl3 in refluxing 1,2-dichloroethane to furnish the target tetracyclic derivative. Resolution was then achieved by chiral MPLC.

1 Tetrahedron 1996, 51, 16, 5867-80.
2 El Achad, R.; Görbig, D.M.; Camps, P.; et al.; Synthesis, in vitro pharmacology, and molecular modeling of very potent tacrine - Huperzine A hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of Alzheimer's disease. J Med Chem 1999, 42, 17, 3227.
3 Contreras Lascorz, J.; El Achab, R.; Camps Garcia, P.; Baños Diez, J.E.; Muñoz-Torrero Lopez-Ibarra, D.; Badia Sancho, A.; Morral Cardoner, J.; Simon Fornell, M.; Görbig Romeu, M.; Vivas, N.M. (Medichem SA); Polycyclic aminopyridine cpds. which are acetylcholinesterase inhibitors, process for preparing them and their use. EP 0796849; ES 2100129; US 5965569; WO 9713754 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 37697 bicyclo[3.3.1]nonane-3,7-dione C9H12O2 详情 详情
(II) 37698 3-ethyl-2-oxatricyclo[3.3.1.1(3,7)]decan-1-ol C11H18O2 详情 详情
(III) 37699 3-ethyl-2-oxatricyclo[3.3.1.1(3,7)]dec-1-yl methanesulfonate C12H20O4S 详情 详情
(IV) 37700 7-ethylbicyclo[3.3.1]non-6-en-3-one C11H16O 详情 详情
(V) 37702 2-amino-4-fluorobenzonitrile C7H5FN2 详情 详情

合成路线3

该中间体在本合成路线中的序号:(IV)

Condensation of diketone (I) with the organocerium reagent derived from methylmagnesium bromide and CeCl3 afforded the oxaadamantanol (II), which was further converted to mesylate (III) upon reaction with methanesulfonyl chloride and Et3N. Subsequent fragmentation of (III) by treatment with silica gel in CH2Cl2 produced bicyclic enone (IV). This was condensed with 2-aminobenzonitrile (V) in the presence of AlCl3 in refluxing 1,2-dichloroethane to furnish the target tetracyclic derivative. Resolution was then achieved by chiral MPLC.

1 Awasthi, S.; Singhal, S.S.; Tetrahedron Asymmetry 1998, 9, 5, 835-849.
2 Tetrahedron 1996, 51, 16, 5867-80.
3 Muñoz-Torrero, D.; Gorbig, D.M.; Simon, M.; Contreras, J.; Camps, P.; Vivas, N.M.; Badia, A.; Banos, J.E.; Synthesis and evaluation of tacrine-huperzine A hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of Alzheimer's disease. Bioorg Med Chem 1998, 6, 4, 427-440.
4 El Achad, R.; Görbig, D.M.; Camps, P.; et al.; Synthesis, in vitro pharmacology, and molecular modeling of very potent tacrine - Huperzine A hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of Alzheimer's disease. J Med Chem 1999, 42, 17, 3227.
5 Contreras Lascorz, J.; El Achab, R.; Camps Garcia, P.; Baños Diez, J.E.; Muñoz-Torrero Lopez-Ibarra, D.; Badia Sancho, A.; Morral Cardoner, J.; Simon Fornell, M.; Görbig Romeu, M.; Vivas, N.M. (Medichem SA); Polycyclic aminopyridine cpds. which are acetylcholinesterase inhibitors, process for preparing them and their use. EP 0796849; ES 2100129; US 5965569; WO 9713754 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 37697 bicyclo[3.3.1]nonane-3,7-dione C9H12O2 详情 详情
(II) 37698 3-ethyl-2-oxatricyclo[3.3.1.1(3,7)]decan-1-ol C11H18O2 详情 详情
(III) 37699 3-ethyl-2-oxatricyclo[3.3.1.1(3,7)]dec-1-yl methanesulfonate C12H20O4S 详情 详情
(IV) 37700 7-ethylbicyclo[3.3.1]non-6-en-3-one C11H16O 详情 详情
(V) 19493 2-aminobenzonitrile 1885-29-6 C7H6N2 详情 详情
Extended Information