WO2019151419A1 - Composé polycarbonyle, dérivé de celui-ci, et procédé de production associé - Google Patents

Composé polycarbonyle, dérivé de celui-ci, et procédé de production associé Download PDF

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Publication number
WO2019151419A1
WO2019151419A1 PCT/JP2019/003442 JP2019003442W WO2019151419A1 WO 2019151419 A1 WO2019151419 A1 WO 2019151419A1 JP 2019003442 W JP2019003442 W JP 2019003442W WO 2019151419 A1 WO2019151419 A1 WO 2019151419A1
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group
compound
formula
polycarbonyl
isopyrazole
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PCT/JP2019/003442
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English (en)
Japanese (ja)
Inventor
泰英 猪熊
翔太 吉岡
光晴 上坂
結大 齋藤
記子 芦田
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国立大学法人北海道大学
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Priority to JP2019569563A priority Critical patent/JP7334965B2/ja
Publication of WO2019151419A1 publication Critical patent/WO2019151419A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • C07C49/15—Ketones containing more than one keto group containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the carbonyl group (—CO—) contains an oxygen atom having a lone pair and a carbon atom having a positive charge, it can undergo various chemical reactions and can be converted into various functional groups. Therefore, since a polycarbonyl compound having a plurality of carbonyl groups can be a raw material for various compounds, it is interesting both academically and industrially.
  • Non-Patent Documents 1 and 2 show that 2,4-dioxo-3 is obtained by allowing silver (I) to act on a silicon enolate prepared from 3,3-dimethyl-2,4-pentanedione in DMSO. Giving linear polycarbonyl oligomers containing 2,3-dimethylpentylene groups as repeat units, with a distinct number of repeat units of 2, 3 or 4, and the oligomers being separated by size exclusion chromatography Reported.
  • Non-patent documents 1 to 3 disclose polycarbonyl compounds having 2,4-dioxo-3,3-dimethylpentylene groups as repeating units and 2, 3, 4 and 8 repeating units. Those production methods were a method by a homocoupling reaction in which the same products were reacted with each other, and a method of repeating the homocoupling reaction. Considering the fact that the reaction is repeated, the yield was not necessarily high enough, so polycarbonyl compounds having a number of other repeating units were not reported, and further, polycarbonyl compounds having a larger number of repeating units were not Not reported.
  • R 1 and R 2 may combine to form a divalent group (eg, represented by —R 1 —R 2 — together with the carbon between the two carbonyl groups An annular structure may be formed),
  • the R 1 , R 2 , and the divalent group formed by combining R 1 and R 2 are each an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an azaalkyl group.
  • a chain compound containing a plurality of isopyrazole rings can be obtained from a chain compound containing a plurality of carbonyl groups. Furthermore, such a chain compound containing a plurality of isopyrazole rings can form a complex with various metal ions, and more preferably, the metal ion can be coordinated with a plurality of chain compounds. That is, the present inventors have found that chain molecules containing a plurality of isopyrazole rings can be bonded by a coordinate bond via a metal to form a macromolecule, so that the present invention has been completed.
  • R 1 and R 2 may combine to form a divalent group (eg, represented by —R 1 —R 2 — together with the carbon between the two carbonyl groups An annular structure may be formed),
  • the R 1 , R 2 , and the divalent group formed by combining R 1 and R 2 are each an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an azaalkyl group. May have at least one substituent selected from a group, an azaaryl group, a thioalkyl group, a thioaryl group and a halogeno group, q is 1 or more]. 14-2.
  • R 1 and R 2 are each independently a group consisting of an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an azaalkyl group, an azaaryl group, a thioalkyl group, a thioaryl group, and a halogeno group.
  • Trimethylchlorosilane (119 mL, 0.94 mmol) was added to the solution, and then the solution was maintained at about 0 ° C., and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) (DBU) ( 151 mL, 1.01 mmol) was added.
  • DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
  • the reaction mixture was heated to reflux for 1 hour. After the reaction mixture was cooled to room temperature, hexane (250 mL) was added to give a two-phase solution. After separating the upper phase (hexane phase), the product was extracted from the dichloromethane phase using hexane (200 mL ⁇ 3).
  • To 2 mL of chloroform solution of 100 mg was added 2 mL of 119 mg of nickel (II) nitrate hexahydrate in ethanol and stirred at room temperature for 1 hour. This solution was allowed to stand at room temperature for 1 day to produce purple crystals. The crystals were collected by filtration and washed with 3 mL of ethanol to obtain 95.4 mg of complex crystals in a
  • This solution was passed through an about 3 cm silica gel column, and the product was further extracted with a dichloromethane solvent containing 10% methanol.
  • the solvent was distilled off with a rotary evaporator to obtain 9.41 g of a crude product.
  • the crude product was dissolved in a mixed solvent of 30 mL of methanol and 40 mL of dichloromethane, 6 mL of 3 M hydrochloric acid was added thereto, and the mixture was stirred at room temperature for 20 minutes. After neutralization with saturated aqueous sodium bicarbonate, extraction was performed twice with 100 mL of dichloromethane, and the organic layer was further washed with 200 mL of saturated brine.
  • FIG. 4 shows the 1 H NMR spectrum of the product.
  • the analysis results are shown in the figure.
  • FIG. 5 shows high performance liquid chromatography of the product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

L'invention concerne : un composé polycarbonyle et un dérivé de celui-ci. Le composé polycarbonyle comprend une structure chimique représentée par la formule (1n). L'invention concerne également : un composé furannique comprenant une structure chimique représentée par la formule (2m) ; et un composé d'isopyrazole représenté par la formule (3p). R1 et R2 sont chacun indépendamment choisis dans un groupe constitué d'un groupe alkyle, un groupe cycloalkyle, un groupe aryle, un groupe alcoxy, un groupe cycloalcoxy, un groupe aryloxy, un groupe azaalkyle, un groupe azaaryle, un groupe thioalkyle, un groupe thioaryle et un groupe halogéno. En variante, R1 et R2 peuvent se lier pour former un groupe divalent.
PCT/JP2019/003442 2018-02-02 2019-01-31 Composé polycarbonyle, dérivé de celui-ci, et procédé de production associé WO2019151419A1 (fr)

Priority Applications (1)

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JP2019569563A JP7334965B2 (ja) 2018-02-02 2019-01-31 ポリカルボニル化合物、その誘導体及びそれらの製造方法

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JP2018017420 2018-02-02
JP2018-017420 2018-02-02
JP2018017419 2018-02-02
JP2018-017419 2018-02-02

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WO2019151419A1 true WO2019151419A1 (fr) 2019-08-08

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001117235A (ja) * 1999-08-06 2001-04-27 Hyundai Electronics Ind Co Ltd フォトレジスト単量体とその製造方法、フォトレジスト重合体とその製造方法、これを利用したフォトレジスト組成物、及び、半導体素子

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001117235A (ja) * 1999-08-06 2001-04-27 Hyundai Electronics Ind Co Ltd フォトレジスト単量体とその製造方法、フォトレジスト重合体とその製造方法、これを利用したフォトレジスト組成物、及び、半導体素子

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
ASHIDA, Y. ET AL.: "Control over coordination self- assembly of flexible, multidentate ligands by stepwise metal coordination of isopyrazole subunits", DAL TON TRANSACTIONS, vol. 48, no. 3, 21 January 2019 (2019-01-21), pages 818 - 822 *
BEALS, R.E. ET AL.: "The condensation of 3- pentanone with furan", JOURNAL OF ORGANIC CHEMISTRY, vol. 21, no. 4, 1956, pages 447 - 448, XP055630874 *
INOKUMA, YASUHIDE: "Endless variety of carbonyl chains', Aliphatic polycarbonyl compounds that can induce flexible and various structures", CHEMISTRY AND CHEMICAL INDUSTRY, vol. 71, no. 10, 2018, pages 822 - 823 *
INOKUMA, YASUHIDE: "Magic rope Carbonyl chains' made of molecules - Opening the way to synthesize large molecules whose nanostructures are precisely controlled", CHEMISTRY, September 2018 (2018-09-01), pages 41 - 46 *
KHROUF, A. ET AL.: "Polyesters bearing furan moieties. Part 2. A detailed investigation of the polytransesterification of difuranic diesters with different diols", MACROMOLECULAR CHEMISTRY AND PHYSICS, vol. 199, no. 12, 1998, pages 2755 - 2765, XP000804378 *
SAITO, YUUTA ET AL.: "Efficient diketone transformation reaction on aliphatic polyketones with high-density carbonyl groups", LECTURE PROCEEDINGS, vol. 98 th, no. 1F2-35, March 2018 (2018-03-01), XP055630872 *
UESAKA, MITSUHARU ET AL.: "Synthesis of aliphatic carbonyl compounds having 16 carbonyl groups in the molecule", LECTURE PROCEEDINGS ( CD- ROM ) OF THE SPRING ANNUAL CONFERENCE OF THE CHEMICAL SOCIETY OF JAPAN, vol. 97 th, no. 3F6-50 *
VALÉRIE BÉNÉTEAU ET AL.: "A rational approach to calix[n]furan precursors", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, vol. 2001, no. 24, 11 December 2001 (2001-12-11), pages 3297 - 3304, XP055630873 *
YOSHIOKA, SHOTA ET AL.: "Efficient oligomer synthesis by oxidative coupling reaction of acetylacetone derivatives", LECTURE PROCEEDINGS ( CD-ROM ) OF THE SPRING ANNUAL CONFERENCE OF THE CHEMICAL SOCIETY OF JAPAN, vol. 97 th, no. 3F6-48, 2017, XP055630872 *

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JPWO2019151419A1 (ja) 2021-02-12

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