2-oxetanone derivative and process for production thereof
View Patent ↗An aldehyde derivative represented by the general formula (2) is reacted with ketene in the presence of a Lewis acid catalyst to produce a novel 2-oxetanone derivative (1), which is then purified to a 2-oxetanone derivative having a high trans-isomer purity, and then converted to a vinyl derivative (3) through decarboxylation reaction.
1. A 2-oxetanone derivative represented by the general formula (1):
wherein R 1 is hydrogen, alkyl having 1 to 20 carbons, halogen, —C≡N, —C≡C—C≡N, —N═C═O or —N═C═S, wherein arbitrary hydrogen may be replaced by halogen in the alkyl;
A 1 , A 2 , A 3 and A 4 are each independently 1,4-cyclohexylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, decahydronaphthalen-2,6-diyl, 1,2,3,4-tetrahydronaphthalen-2,6-diyl or naphthalen-2,6-diyl, provided that when A 1 , A 2 and A 3 are each 1,4-cyclohexylene, the steric configuration thereof is trans, and when A 4 is 1,4-cyclohexylene, the steric configuration thereof may be trans, cis or a mixture of trans and cis;
Z 1 , Z 2 , Z 3 and Z 4 are each independently a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH 2 O— or —OCH 2 —;
j and k are each independently 0 or 1; l and m are 1; and n is an integer of from 0 to 6.
2. The 2-oxetanone derivative according to claim 1 which is represented by the general formula (1-1):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N;
A 1 , A 2 and A 3 are each independently trans-1,4-cyclohexylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, decahydronaphthalen-2,6-diyl, 1,2,3,4-tetrahydronaphthalen-2,6-diyl or naphthalen-2,6-diyl;
Z 1 , Z 2 and Z 3 are each independently a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH 2 O— or —OCH 2 —;
j and k are each independently 0 or 1; and l is 1.
3. A 2-oxetanone derivative represented by the general formula (1-2):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkoxy having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
4. A 2-oxetanone derivative represented by the general formula (1-3):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkoxy having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
5. A 2-oxetanone derivative represented by the general formula (1-4):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkoxy having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
6. A 2-oxetanone derivative represented by the general formula (1-5):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkoxy having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
7. A 2-oxetanone derivative represented by the general formula (1-6):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkoxy having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
8. A 2-oxetanone derivative represented by the general formula (1-7):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkoxy having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
9. A 2-oxetanone derivative represented by the general formula (1-8):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkenyl having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
10. The 2-oxetanone derivative according to claim 1 which is represented by the general formula (1-9):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N;
A 1 , A 2 and A 3 are each independently trans-1,4-cyclohexylene, 1,4-phenylene in which arbitrary hydrogen may be replaced by fluorine, decahydronaphthalen-2,6-diyl, 1,2,3,4-tetrahydronaphthalen-2,6-diyl or naphthalen-2,6-diyl;
Z 1 , Z 2 and Z 3 are each independently a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH 2 O— or —OCH 2 —;
j and k are each independently 0 or 1; and l is 1.
11. A 2-oxetanone derivative represented by the general formula (1-10):
wherein R 1 is hydrogen, alkyl having 1 to 15 carbons, alkoxy having 1 to 15 carbons, halogenated alkyl having 1 to 15 carbons, halogenated alkoxy having 1 to 15 carbons, alkenyl having 2 to 10 carbons, halogen or —C≡N.
12. 4-(4-(trans-4-propylcyclohexyl)cyclohexyl)-2-oxetanone, 4-(4-(trans-4-butylcyclohexyl)cyclohexyl)-2-oxetanone or 4-(4-(trans-4-pentylcyclohexyl)cyclohexyl)-2-oxetanone.