TOP > 外国特許検索 > METHOD OF MANUFACTURING TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, METHOD OF MANUFACTURING TRIFLUOROMETHYL COMPOUND STARTING FROM TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, AND TRIFLUOROMETHYL GROUP-CONTAINING COMPOUND

METHOD OF MANUFACTURING TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, METHOD OF MANUFACTURING TRIFLUOROMETHYL COMPOUND STARTING FROM TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, AND TRIFLUOROMETHYL GROUP-CONTAINING COMPOUND コモンズ

外国特許コード F160008860
整理番号 NU-659
掲載日 2016年9月28日
出願国 世界知的所有権機関(WIPO)
国際出願番号 2016JP066988
国際公開番号 WO 2016199789
国際出願日 平成28年6月8日(2016.6.8)
国際公開日 平成28年12月15日(2016.12.15)
優先権データ
  • 特願2015-116151 (2015.6.8) JP
  • 特願2015-150175 (2015.7.29) JP
発明の名称 (英語) METHOD OF MANUFACTURING TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, METHOD OF MANUFACTURING TRIFLUOROMETHYL COMPOUND STARTING FROM TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, AND TRIFLUOROMETHYL GROUP-CONTAINING COMPOUND コモンズ
発明の概要(英語) The present invention addresses the problem of efficiently synthesizing a trifluoromethyl substituted semisquarate in a short process, in order to manufacture trifluoromethyl compounds with various functionalities. A method was developed of synthesizing a trifluoromethyl substituted semisquarate with squarate as a starting material, in the two steps of a trifluoromethylation reaction and an allyl alcohol transfer reaction. Furthermore, a method was established of manufacturing trifluoromethyl compounds with various functionalities starting from a trifluoromethyl substituted semisquarate.
特許請求の範囲(英語) [claim1]
1. Is displayed with the below-mentioned general formula (1) the chemical compound which as starting raw materials,
(The inside R of formula is the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.)
Addition reaction process,
The method of producing the chemical compound where the trifluoromethyl basis is introduced and by ring enlargement process.
[claim2]
2. The aforementioned trifluoromethyl basis is introduced the chemical compound where,
Production method of the claim 1 statement which is the quinone compound.
[claim3]
3. The trifluoromethyl basis is introduced the quinone compound where,
The below-mentioned general formula production method of the claim 2 statement which is the chemical compound which is displayed with (4) or (5).
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (1), R (2), R (3), R (4) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, is selected from alkoxy group, the [kuroro] basis, the fluoro basis and the ester basis, R (1)-R the substituent which (4) the inside optional two adjoins may form reduction ring benzene.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (5), R (6) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, is selected from alkoxy group, the [kuroro] basis and the fluoro basis.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
[claim4]
4. The aforementioned trifluoromethyl basis is introduced the chemical compound where,
Production method of the claim 1 statement which is complex ring reduction ring chemical compound.
[claim5]
5. The trifluoromethyl basis is introduced the complex ring reduction ring chemical compound where,
The below-mentioned general formula (6) or (7) with production method of the claim 4 statement which is the chemical compound which is displayed.
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (7), R (8) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, it is selected from alkoxy group, the [kuroro] basis and the fluoro basis R (7), R (8) connecting, it is possible to form reduction ring benzene.
X is O, S and NP, P, [karubameto], is sulfonamide.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
X is CH=CH, S and NCH [3].)
[claim6]
6. The aforementioned trifluoromethyl basis is introduced the chemical compound where,
Production method of the claim 1 statement which is the hydroquinone compound.
[claim7]
7. The trifluoromethyl basis is introduced the hydroquinone compound where,
The below-mentioned general formula (8) the - (10) production method of the claim 6 statement which is the chemical compound which is displayed with in each case.
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (9), R (10), R (11), R (12) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, it is selected from alkoxy group, the [kuroro] basis, the fluoro basis and the ester basis, R (9) -R (12) the substituent which the inside optional two adjoins may form reduction ring benzene.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (13), R (14) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, it is selected from alkoxy group, the [kuroro] basis and the fluoro basis.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (15), R (16) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, it is selected from alkoxy group, the [kuroro] basis and the fluoro basis R (15), R (16) connecting, it is possible to form reduction ring benzene.
X is O, S and NP, P, [karubameto], is sulfonamide.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
[claim8]
8. The aforementioned trifluoromethyl basis is introduced the chemical compound where,
Production method of the claim 1 statement which is [butenorido] chemical compound.
[claim9]
9. The trifluoromethyl basis is introduced the [butenorido] chemical compound where,
The below-mentioned general formula (10-1) and (10-2) with production method of the claim 8 statement which is the chemical compound which is displayed.
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (17), R (18), R (19), R (20) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, it is selected from alkoxy group, the [kuroro] basis, the fluoro basis and the ester basis, R (17) -R (20) the substituent which the inside optional two adjoins may form reduction ring benzene.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (21), R (22) becoming independent respectively, hydrogen, the alkyl group and the [arukeniru] basis, it is selected from alkoxy group, the [kuroro] basis and the fluoro basis R (21), R (22) connecting, it is possible to form reduction ring benzene.
X is O, S and NP, P, [karubameto], is sulfonamide.
Here, the alkyl group and the [arukeniru] basis, the hydrocarbon region of alkoxy group, the direct condition and divergence condition of C1-C8, is good with annular in each case.)
[claim10]
10. The aforementioned trifluoromethyl basis is introduced the chemical compound where,
Production method of the claim 1 statement which is four member ring chemical compounds.
[claim11]
11. The trifluoromethyl basis is introduced four member ring chemical compounds where,
The below-mentioned general formula (10-3c) and (10-3d) with production method of the claim 10 statement which is the chemical compound which is displayed.
(In formula, R (23), R (24) becoming independent respectively, C1-C6 direct condition and divergence condition, it is selected from the annular alkyl group or phenyl group.)
(In formula, R (25), R (26) becoming independent respectively, C1-C6 direct condition and divergence condition, it is selected from the annular alkyl group or phenyl group.)
[claim12]
12. The aforementioned trifluoromethyl basis is introduced the chemical compound where,
Production method of the claim 1 statement which is [bishikuro] ring chemical compound.
[claim13]
13. The trifluoromethyl basis is introduced the [bishikuro] ring chemical compound where,
The below-mentioned general formula (37-1) with production method of the claim 12 statement which is the chemical compound which is displayed.
(In formula, R (27), R (28) becoming independent respectively, C1-C6 direct condition and divergence condition, it is selected from the annular alkyl group, or phenyl group R (27), R (28) with is possible to form ring structure.)
[claim14]
14. The aforementioned trifluoromethyl basis is introduced the chemical compound where,
Production method of the claim 1 statement which is the amino cyclopentene dione compound.
[claim15]
15. The trifluoromethyl basis is introduced the amino cyclopentene dione compound where,
The below-mentioned general formula (10-4) with production method of the claim 14 statement which is the chemical compound which is displayed.
(In formula, R is selected from the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.
R (29) with the alkyl group of C1-C8, direct condition and divergence condition, it is good with annular in each case.
R (30) the [t]-buchiru basis or 1,1,3,3 - it is selected from the tetramethyl butyl basis.)
[claim16]
16. Is displayed with the below-mentioned general formula (1) being production method of the trifluoromethyl substitution semi Skua rate which,
The below-mentioned general formula depending on the process which the Skua rate which is displayed with (3) to trifluoromethyl is converted,
Is displayed with the below-mentioned general formula (2) the chemical compound which is produced,
The production method of featuring that it synthesizes with the process which does the allyl alcoholic transfer reaction.
(The inside R of formula also is possible to be the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis, be the basis which differs to be the identical basis.)
[claim17]
17. Is displayed with the below-mentioned general formula (1) being production method of the trifluoromethyl substitution semi Skua rate which,
(The inside R of formula is the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.)
The below-mentioned general formula the chemical compound which is displayed with (2)
The production method of featuring that it synthesizes with the process which does the allyl alcoholic transfer reaction.
(The inside R of formula also is possible to be the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis, be the basis which differs to be the identical basis.)
[claim18]
18. Claim being production method of trifluoromethyl substitution semi Skua rate of 16 or 17 statements,
Does the allyl alcoholic transfer reaction the process which,
Re [2] O [7] or PH [3] SiReO [the production method of featuring that it is the reaction which uses 3] as the catalyst.
[claim19]
19. Is displayed with the below-mentioned general formula (2) being production method of the chemical compound which,
The below-mentioned general formula the Skua rate which is displayed with (3)
The production method of featuring that it synthesizes to trifluoromethyl with the process which is converted.
(The inside R of formula also is possible to be the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis, be the basis which differs to be the identical basis.)
[claim20]
20. Claim being production method of 16 or 19 statements,
The to aforementioned trifluoromethyl is converted the process which,
The process which does the [shirirutorihuruoromechiru] Si conversion reaction CF [3] Me [3] as the organic silicon reagent using and,
The production method of featuring that it consists of about deviation from [shiriru] chemical engineering.
[claim21]
21. The below-mentioned general formula the chemical compound which is displayed with (1).
(The inside R of formula is the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis.)
[claim22]
22. The below-mentioned general formula (2) chemical compound.
(The inside R of formula also is possible to be the isopropyl basis, the [n]-puropiru basis, the [t]-buchiru basis, the [isobuchiru] basis and the [sec]-buchiru basis, be the basis which differs to be the identical basis.)
[claim23]
23. The below-mentioned formula (12) the - (52), (17-1), (10-3a) and (10-3b) with the trifluoromethyl compound which is displayed.
  • 出願人(英語)
  • ※2012年7月以前掲載分については米国以外のすべての指定国
  • NAGOYA UNIVERSITY
  • 発明者(英語)
  • YAMAMOTO YOSHIHIKO
  • KUROHARA TAKASHI
  • SHIBUYA MASATOSHI
国際特許分類(IPC)
指定国 (WO2016199789)
National States: AE AG AL AM AO AT AU AZ BA BB BG BH BN BR BW BY BZ CA CH CL CN CO CR CU CZ DE DK DM DO DZ EC EE EG ES FI GB GD GE GH GM GT HN HR HU ID IL IN IR IS JP KE KG KN KP KR KZ LA LC LK LR LS LU LY MA MD ME MG MK MN MW MX MY MZ NA NG NI NO NZ OM PA PE PG PH PL PT QA RO RS RU RW SA SC SD SE SG SK SL SM ST SV SY TH TJ TM TN TR TT TZ UA UG US UZ VC VN ZA ZM ZW
ARIPO: BW GH GM KE LR LS MW MZ NA RW SD SL SZ TZ UG ZM ZW
EAPO: AM AZ BY KG KZ RU TJ TM
EPO: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
OAPI: BF BJ CF CG CI CM GA GN GQ GW KM ML MR NE SN ST TD TG
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