JP7485277B2 - 芳香族環状化合物及びその製造方法 - Google Patents
芳香族環状化合物及びその製造方法 Download PDFInfo
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- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
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- 239000004305 biphenyl Substances 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- DZNFQIYYEXFFGV-UHFFFAOYSA-M chloropalladium(1+) 2-phenylaniline tritert-butylphosphane Chemical compound [Pd+]Cl.CC(C)(C)P(C(C)(C)C)C(C)(C)C.NC1=CC=CC=C1C1=CC=CC=[C-]1 DZNFQIYYEXFFGV-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
1.下記式(1)で表される芳香族環状化合物。
Ar1~Ar3は、それぞれ独立に、炭素数6~20のアリーレン基であり、該アリーレン基の水素原子の一部又は全部が、ハロゲン原子、シアノ基、炭素数1~20のアルキル基、炭素数1~20のアルコキシ基又は炭素数2~20のアルコキシカルボニル基で置換されていてもよく、該アルキル基、アルコキシ基及びアルコキシカルボニル基のメチレン基の一部が、エーテル結合で置換されていてもよい。]
2.Rが、式(2)で表される基である1の芳香族環状化合物。
3.Xが、下記式(X1)~(X11)のいずれかで表される基である1又は2の芳香族環状化合物。
4.R1及びR2が、それぞれ独立に、炭素数1~10のアルカンジイル基である1~3のいずれかの芳香族環状化合物。
5.Ar1~Ar3が、それぞれ独立に、下記式(3)で表される基である1~4のいずれかの芳香族環状化合物。
6.Ar1及びAr2が、p-フェニレン基である5の芳香族環状化合物。
7.Ar3が、式(3)で表される基であって、R11及びR14が、それぞれ独立に、炭素数1~10のアルコキシ基であり、R12及びR13が、水素原子である5又は6の芳香族環状化合物。
8.下記式(1A)で表される化合物と下記式(1B)で表される化合物とをカップリング反応させる、下記式(1)で表される芳香族環状化合物の製造方法。
Ar1~Ar3は、それぞれ独立に、炭素数6~20のアリーレン基であり、該アリーレン基の水素原子の一部又は全部が、ハロゲン原子、シアノ基、炭素数1~20のアルキル基、炭素数1~20のアルコキシ基又は炭素数2~20のアルコキシカルボニル基で置換されていてもよく、該アルキル基、アルコキシ基及びアルコキシカルボニル基のメチレン基の一部が、エーテル結合で置換されていてもよい。
X1及びX2は、下記式(1A-1)又は(1A-2)で表される基であり、X3及びX4は、ハロゲン原子又は擬ハロゲン基である。
前記芳香族環状化合物は、下記スキームAに示されるように、下記式(1A)で表される化合物と下記式(1B)で表される化合物とをカップリング反応させることで製造することができる。なお、スキームAでは例として鈴木・宮浦カップリング反応を利用した合成方法を示しているが、他のカップリング反応を利用して合成することも可能である。
1H-NMR:JEOL ECA-500 and ECA-600
13C-NMR:JEOL ECA-500 and ECA-600
IR:JASCO FT/IR-410
1H-NMR (500MHz, DMSO) δ 8.60 (s, 4H), 4.86 (t, J=5.4Hz, 2H), 4.16 (q, J=6.4Hz, 2H), 3.66 (q, J=5.9Hz, 4H).
IR (KBr) 2960, 1694, 1645, 1578, 1455, 1334, 1247, 1180, 1060, 856, 770 cm-1.
1H-NMR (500MHz, CDCl3) δ 8.77 (s, 4H), 7.91 (d, J=8.6Hz, 4H), 7.80 (d, J=8.6Hz, 4H), 4.68 (s, 8H), 1.34 (quint, J=7.5Hz, 4H).
13C-NMR (150MHz, CDCl3) δ 166.5, 162.8, 134.6, 131.8, 131.1, 128.6, 126.8, 126.5, 84.1, 62.2, 39.5, 24.9.
IR (KBr) 2979, 1709, 1671, 1582, 1509, 1454, 1399, 1361, 1268, 1145, 1111, 1020, 858, 770, 710 cm-1.
三方コックを備えた20mLナスフラスコに、化合物B33.0mg(0.067mmol)、化合物A41.2mg(0.051mmol)、フッ化セシウム32.0mg(0.21mmol)、18-クラウン-6 103mg(0.39mmol)及び(tBu3P)Pd G2 プレ触媒1.27mg(0.0025mmol)を加え、アルゴンで置換した。窒素気流下で乾燥THF6.0mL及び蒸留水0.2mLを加え、脱気してからアルゴンで置換し、室温で3日間攪拌した。反応溶液をろ過し、ろ液に1mol/L塩酸を加え、クロロホルムで抽出し、飽和塩化カリウム水溶液で3回洗浄して無水硫酸マグネシウムを加えた。ろ過後、減圧下で溶媒を留去し、黒茶色固体58.9mg(粗収率132%)を得た。この粗生成物をカラムクロマトグラフィー(充填剤:SiO2、展開溶媒:ヘキサン/酢酸エチル=3/2)を行って精製し、芳香族環状化合物Aを茶橙色固体として得た(収量13.6mg、収率30%)。
1H-NMR (600MHz, CDCl3) δ= 8.42 (s, 4H), 7.83 (d, J=8.6Hz, 4H), 7.46 (d, J=8.0Hz, 4H), 6.83 (s, 2H), 4.54 (m, 8H), 3.94 (m, 2H), 3.83 (m, 2H), 2.07 (m, 1H), 1.71 (m, 16H), 0.90 (m, 4H).
1H-NMR (500MHz, CDCl3) δ 8.73 (s, 4H), 7.99 (d, J=8.2Hz, 4H), 7.85 (d, J=7.6Hz, 4H), 4.36 (t, J=6.5Hz, 4H), 4.25 (t, J=7.6Hz, 4H), 1.90 (m, 8H), 1.62 (m, 4H), 1.36 (s, 24H).
13C-NMR (150MHz, CDCl3) δ 166.5, 162.7, 134.5, 132.4, 130.9, 128.5, 126.6, 126.5, 84.1, 64.8, 40.5, 28.3, 27.6, 24.8, 23.5.
IR (KBr) 3449, 2980, 1704, 1667, 1581, 1509, 1455, 1399, 1256, 1171, 1143, 1117, 1019, 964, 860, 771, 711, 652 cm-1.
三方コックを備えた50mLナスフラスコに、化合物D113.0mg(0.27mmol)、化合物C180mg(0.20mmol)、フッ化セシウム127.0mg(0.84mmol)、18-クラウン-6 429mg(1.62mmol)及び(tBu3P)Pd G2プレ触媒5.23mg(0.010mmol)を加えて、アルゴンで置換した。窒素気流下で乾燥THF24.0mL及び蒸留水0.8mLを加え、脱気してからアルゴンで置換し、室温で3日間攪拌した。反応溶液をろ過し、ろ液に1mol/L塩酸を加え、クロロホルムで抽出、飽和塩化カリウム水溶液で3回洗浄して無水硫酸マグネシウムを加えた。ろ過後、減圧下で溶媒を留去して黒茶色固体322mg(粗収率180%)を得た。この粗生成物をカラムクロマトグラフィー(充填剤:SiO2、展開溶媒:ヘキサン/酢酸エチル=3/2)を行って精製し、芳香族環状化合物Bを茶橙色固体として(収量13.6mg、収率30%)を得た。
1H-NMR (600MHz, CDCl3) δ= 8.57 (s, 4H), 8.13 (d, J=8.2Hz, 4H), 7.63 (d, J=8.2Hz, 4H), 6.92 (s, 2H), 4.52 (m, 4H), 4.07 (m, 4H), 3.88 (t, J=7.2Hz, 2H), 1.91 (m, 4H), 1.85 (m, 4H), 1.75 (m, 4H), 1.71 (quint, J=7.0Hz, 4H), 1.40 (quint, J=7.0Hz, 4H), 1.27 (m, 8H), 0.86 (t, J=6.9Hz, 6H).
1H-NMR (CDCl3, 500MHz) δ 8.01 (d, J=8.0Hz, 4H), 7.86 (d, J=8.6Hz, 4H), 4.32 (t, J=6.6Hz, 4H), 1.40 (m, 36H).
IR (KBr) 1509, 1362, 1281, 1020 cm-1.
1H-NMR (500MHz, CDCl3) δ 7.80 (d, J=8.6Hz, 4H), 7.64 (d, J=8.9Hz, 4H), 6.85 (s, 2H), 4.55-4.52 (m, 2H), 4.14-4.10 (m, 2H), 4.06-4.01 (m, 2H), 3.95-3.91 (m, 2H), 1.79 (quint, J=7.1Hz, 4H), 1.48-1.40 (m, 8H), 0.91-0.81 (m, 22H).
化合物Cを10mLの試料瓶に入れ、ハンディUVランプ(アズワン(株)製、型式SLUV-8)を用いて波長254nmの紫外線を照射した。その結果、化合物Cから緑色の蛍光が観察された。
Claims (3)
- Rが、式(2)で表される基である請求項1記載の芳香族環状化合物。
- 下記式(1A)で表される化合物と下記式(1B)で表される化合物とをカップリング反応させる、下記式(1)で表される芳香族環状化合物の製造方法。
Ar1 及びAr 2 は、1,4-フェニレン基であり、Ar3は、下記式(3)で表される基である。
X1及びX2は、下記式(1A-1)又は(1A-2)で表される基であり、X3及びX4は、ハロゲン原子又は擬ハロゲン基である。
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