Biaryl-type compounds, CD color fixing agent and method for determination of absolute configuration
AssigneeKanazawa University
InventorsTomihisa Ohta, Shinzo Hosoi
Life of this patent
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Abstract
A novel achiral biaryl-type compound and a circular dichroism(CD) color fixing agent are provided. Furthermore, a method for determining an absolute configuration of a chiral compound is carried out by introducing the above achiral biaryl-type compound into the chiral compound.
Claims5
An achiral biaryl-type compound in which the biaryl-type compound is at least one compound selected from the group consisting of a biphenyl dicarboxylic acid derivative represented by the following general formula (I):
- 40
- (wherein R is H, Me-, Et-, i-Pt-, n-Bu-, i-Bu- or t-Bu- and X is H, Me-, Me2N—, MeO—, NO2—, NH2—, CN—, Cl or Br, and Y is OH—, CN—,
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- provided that X is Me2N— or CN— when R═H and Y═OH, X is Me-, Me2N—, NO2—, NH2— or CN— when R=Me and Y═OH, and X is Me-, Me2N—, MeO—, NO2—, NH2— or CN— when R=Et and Y═OH, and R is t-Bu- when X═H and Y═OH), 2,2′-binaphthyl dicarboxylic acid derivative represented by the following general formula (II):
- 42
- (wherein R is H, Me-, Et-, i-Pr-, n-Bu-, i-Bu- or t-Bu- and Y is OH—, CN—,
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- provided that R is i-Pr-, n-Bu-,.i-Bu- or t-Bu- when Y═OH), 2,2′-biquinoline dicarboxylic acid and derivatives thereof represented by the following general formula (III):
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- (wherein R is H, Me-, Et-, i-Pr-, n-Bu-, i-Bu- or t-Bu- and Y is OH—, CN—,
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- and may contain a compound formed by cyclizing —CO2R with —COY to form
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- ), 7,7′-biquinoline dicarboxylic acid and derivatives thereof represented by the following general formula (IV):
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- (wherein R is H, Me-, Et-, i-Pr-, n-Bu-, i-Bu- or t-Bu- and Y is OH—, CN—,
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- and may contain a compound formed by cyclizing —CO2R with —COY to form
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- ), 2,2′-bianthracene dicarboxylic acid and derivatives thereof represented by the following general formula (V):
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- (wherein R is H, Me-, Et-, i-Pr-, n-Bu-, i-Bu- or t-Bu- and Y is OH—, CN—,
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- and may contain a compound formed by cyclizing —CO2R with —COY to form
- 52
- ), 2,2′-bibenzo(g)quinoline dicarboxylic acid and derivatives thereof represented by the following general formula (VI):
- 53
- (wherein R is H, Me-, Et-, i-Pr-, n-Bu-, i-Bu- or t-Bu- and Y is OH—, CN—,
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- and may contain a compound formed by cyclizing —CO2R with —COY to form
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- ), and 3,3′-biacridine dicarboxylic acid and derivatives thereof represented by the following general formula (VII):
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- (wherein R is H, Me-, Et-, i-Pr-, n-Bu-, i-Bu- or t-Bu- and Y is OH, CN,
- 57
- and may contain a compound formed by cyclizing —CO2R with —COY to form
- 58
- ).
A circular dichroism,(CD) color fixing agent for introducing an achiral CD chromophore into a chiral compound, in which the chiral compound is selected from the group consisting of alcohols, thiols and amines, and the CD color fixing agent comprises at least one achiral biaryl-type compound selected from the group consisting of 2,2′-binaphthyl dicarboxylic acid, 2,2′-biquinoline dicarboxylic acid, 7,7′-biquinoline dicarboxylic acid, 2,2′-bianthracene dicarboxylic acid, 2,2′-bibenzo(g)quinoline dicarboxylic acid, 3,3′-biacridine dicarboxylic acid and derivatives thereof and a biphenyl dicarboxylic acid derivative other than biphenyl dicarboxylic acid anhydride.
A method for determining an absolute configuration of a chiral compound, which comprises steps of:
- (a) selecting a chiral compound from the group consisting of alcohols, thiols and amines;
- (b) introducing an achiral CD chromophore into the chiral compound;
- and
- (c) determining an absolute configuration of the chiral compound from relative bulkiness of a substituent on α-carbon, preferential order in a sequence rule (CIP method) and sign of exciton chirality.
Dependencies are inferred from the claim text.