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US4029683A Expired / Lapsed US ⏱️ 0.0 years remaining

Copper complex

Assignee: Sumitomo Chemical Co Ltd
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Filing: 1975-12-29
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Granted: 1977-06-14
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Expires: 1995-12-29
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Abstract

Abstract A copper complex coordinated with a Schiff base is provided herein, which complex is especially advantageous to catalyze the asymmetric synthesis of alkyl chrysanthemates. The specific complex of the present invention is a copper complex coordinated with a chiral Schiff base of the formula: <IMAGE> wherein C* is an asymmetric carbon atom, R1 is selected from (a) alkyl groups whose carbon atom number is 1-10, and (b) aralkyl groups with or without alkoxy substituent(s), whose total carbon atom number is 7-20, R2 is selected from aryl groups with alkoxy substituent(s), whose total carbon atom number is 7-30, X is selected from (a) hydrogen, (b) alkyl groups having 1-10 carbon atoms, (c) a phenyl group, (d) alkoxy groups having 1-10 carbon atoms, (e) halogen atoms, (f) nitro, or X is benzo which together with the ring to which it is attached forms a naphthalene ring, and Y is a hydrogen atom.

Inventors

  • 👤 Tadatoshi Aratani
  • 👤 Shuzo Nakamura
  • 👤 Tsuneyuki Nagase
  • 👤 Yukio Yoneyoshi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 00:28
CPC Classifications
C; C07; C07F; C07F1/00; C07F1/08

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 131 words
A compound which is a copper complex coordinated with a chiral Schiff base of the formula: ##STR8## wherein C is an asymmetric carbon atom, R 1 is selected from the group consisting of (a) alkyl groups whose carbon atom number is 1-10, and (b) aralkyl groups with or without alkoxy substituent(s), whose total carbon atom number is 7-20, R 2 is selected from aryl groups with alkoxy substituent(s), whose total carbon atom number is 7-30, X is selected from the group consisting of (a) hydrogen, (b) alkyl groups having 1-10 carbon atoms, (c) phenyl group, (d) alkoxy groups having 1-10 carbon atoms, (e) halogen atoms, (f) nitro, or X is benzo which together with the ring to which it is attached forms a naphthalene ring, and Y is a hydrogen atom.
Claim 2
Dependent Claim 131 words
A compound which is a copper complex coordinated with a chiral Schiff base of the formula: ##STR8## wherein C is an asymmetric carbon atom, R 1 is selected from the group consisting of (a) alkyl groups whose carbon atom number is 1-10, and (b) aralkyl groups with or without alkoxy substituent(s), whose total carbon atom number is 7-20, R 2 is selected from aryl groups with alkoxy substituent(s), whose total carbon atom number is 7-30, X is selected from the group consisting of (a) hydrogen, (b) alkyl groups having 1-10 carbon atoms, (c) phenyl group, (d) alkoxy groups having 1-10 carbon atoms, (e) halogen atoms, (f) nitro, or X is benzo which together with the ring to which it is attached forms a naphthalene ring, and Y is a hydrogen atom.
Claim 3
Dependent Claim 30 words
A compound of claim 1 in which said copper complex has the following structure: ##STR9## wherein R 1 R 2 , X and Y are defined as in claim 1.
Claim 4
Dependent Claim 32 words
The compound of claim 1 in which said copper complex has the following structure: ##STR10## wherein C, R 1 , R 2 , X and Y are defined as in claim 1.
Claim 5
Dependent Claim 29 words
The compound of claim 1 in which R 1 is a. benzyl, b. 4-methoxyphenylmethyl, c. 4-isopropoxyphenylmethyl, d. 4-butoxyphenylmethyl, e. 4-benzyloxyphenylmethyl, f. methyl, g. isopropyl, h. isobutyl, or i. cyclohexylmethyl.
Claim 6
Dependent Claim 32 words
The compound of claim 1 in which R 2 is a. 2-methoxyphenyl, b. 2-ethoxyphenyl, c. 2-isopropoxyphenyl, d. 2-butoxyphenyl, e. 2-octyloxyphenyl, f. 2-benzyloxy-5-methylphenyl, p1 g. 2-butoxy-5-t-butylphenyl, h. 5-t-butyl-2-octyloxyphenyl, i. 4-butoxybiphenyl-3-yl, or j. 2,5-dibutoxyphenyl.
Claim 7
Dependent Claim 71 words
The compound of claim 2 in which said chiral Schiff base is either an (R)- or (S)-enantiomer of the following: a. N-salicylidene-2-amino-1,1-di(2-isopropoxyphenyl)-3-phenyl-1-propanol, b. N-salicylidene-2-amino-1,1-di(2-butoxy-5-t-butylphenyl)-3-phenyl-1-propanol, c. N-salicylidene-2-amino-1,1-di(2-methoxyphenyl)-3-phenyl-1-propanol, d. N-salicylidene-2-amino-1,1-di(2-ethoxyphenyl)-3-phenyl-1-propanol, e. N-salicylidene-2-amino-1,1-di(2-butoxyphenyl)-3-phenyl-1-propanol, f. N-salicylidene-2-amino-1,1-di(2-octyloxy-phenyl)-3-phenyl-1-propanol, g. N-salicylidene-2-amino-1,1-di(2-phenoxyphenyl)-3-phenyl-1-propanol, h. N-salicylidene-2-amino-1,1-di(2-benzyloxy-5-methylphenyl)-3-phenyl-1-propanol, i. N-salicylidene-2-amino-1,1-di(5-t-butyl-2-isopropoxyphenyl)-3-phenyl-1-propanol, j. N-salicylidene-2-amino-1,1-di(5-t-butyl-2-octyloxyphenyl)-3-phenyl-1-propanol, k. N-salicylidene-2-amino-1,1-di(4-butoxybiphenyl-3-yl)-3-phenyl-1-propanol, l. N-salicylidene-2-amino-1,1-di(2,5-dibutoxy-phenyl)-3-phenyl-1-propanol, m. N-salicylidene-2-amino-1,1-di(2-isopropoxyphenyl)-3-(4-isopropoxyphenyl)-1-propanol, n. N-salicylidene-2-amino-1,1-di(5-t-butyl-2-octyloxyphenyl)-3-(4-isopropoxyphenyl)-1-propanol, o. N-salicylidene-2-amino-1,1-di(2-butoxyphenyl)-3-cyclohexyl-1-propanol, p. N-salicylidene-2-amino-1,1-di(2-methoxyphenyl)-4-methyl-1-pentanol, q. N-salicylidene-2-amino-1,1-di(2-butoxy-5-t-butylphenyl)-4-methyl-1-pentanol, r. N-salicylidene-2-amino-1,1-di(2-benzyloxy-5-t-butylphenyl)-4-methyl-1-pentanol, s. N-salicylidene-2-amino-1,1-di(2-butoxy-5-t-butylphenyl)-1-propanol, t. N-salicylidene-2-amino-1,1-di(2-butoxyphenyl)-3-methyl-1-butanol, u. N-salicylidene-2-amino-1,1-di(2-butoxyphenyl)-1-propanol, v. N-(3,5-dibromosalicylidene)-2-amino-1,1-di(2-isopropoxyphenyl)-3-phenyl-1-propanol, w. N-(3-ethoxysalicylidene)-2-amino-1,1-di(2-isopropoxyphenyl)-3-phenyl-1-propanol, x. N-(2-hydroxy-1-naphthylmethylene)-2-amino-1,1-di(2-isopropoxyphenyl)-3-phenyl-1-propanol, or y. N-salicylidene-2-amino-1,1-di(4-butoxybiphenyl-3-yl)-1-propanol.
Claim 8
Dependent Claim 27 words
The compound of claim 3 in which said chiral Schiff base is either an (R)- or (S)-enantiomer of the following: a. N-salicylidene-2-amino-1,1-di(2-methoxyphenyl)-3-phenyl-1-propanol, b. N-salicylidene-2-amino-1,1-di(3-methoxyphenyl)-3-phenyl-1-propanol, or c. N-salicylidene-2-amino-1,1-di(2-methoxyphenyl)-4-methyl-1-pentanol.

References Cited (Backward Citations)

US2300998A Cited
US2381952A Cited
GB740014A Cited
US3357883A Cited
BE787473A Cited
US3868401A Cited
BE810959A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-06-13 1980-12-13 1981-06-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-06-13 1984-12-13 1985-06-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-06-13 1988-12-13 1989-06-14 $7700.00 Window Closed / Lapsed

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