Home Cart 0 Sign in  

[ CAS No. 641-57-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 641-57-6
Chemical Structure| 641-57-6
Structure of 641-57-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 641-57-6 ]

Related Doc. of [ 641-57-6 ]

Alternatived Products of [ 641-57-6 ]

Product Details of [ 641-57-6 ]

CAS No. :641-57-6 MDL No. :MFCD00854215
Formula : C27H16O Boiling Point : -
Linear Structure Formula :- InChI Key :QQGHPFDLUNMBGJ-UHFFFAOYSA-N
M.W : 356.42 Pubchem ID :267145
Synonyms :

Safety of [ 641-57-6 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 641-57-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 641-57-6 ]

[ 641-57-6 ] Synthesis Path-Downstream   1~57

  • 1
  • [ 641-57-6 ]
  • [ 14568-68-4 ]
  • [ 103510-88-9 ]
YieldReaction ConditionsOperation in experiment
With toluene
  • 2
  • [ 641-57-6 ]
  • [ 63444-51-9 ]
  • [ 2026-95-1 ]
  • 3
  • [ 641-57-6 ]
  • [ 63600-35-1 ]
  • [ 2011-26-9 ]
YieldReaction ConditionsOperation in experiment
With toluene
  • 4
  • [ 641-57-6 ]
  • [ 55087-78-0 ]
YieldReaction ConditionsOperation in experiment
With phenanthrene; acetylene at 250 - 280℃;
With ethyl-vinyl ether at 180 - 200℃;
With n-butylvinyl ether at 180 - 200℃;
With bis(2-vinylphenyl) ether at 180 - 200℃;
With vinyl formate at 180 - 200℃;
With Vinyl bromide at 180 - 200℃;
With ethylene dibromide at 200 - 240℃;
Multi-step reaction with 2 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 20 h / 230 °C / Autoclave; Inert atmosphere 2: hydrogenchloride / water; tetrahydrofuran / 10 h / Reflux
Multi-step reaction with 2 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 20 h / 230 °C / Sealed tube; Inert atmosphere 2: hydrogenchloride / tetrahydrofuran / 10 h / Reflux

  • 5
  • [ 641-57-6 ]
  • [ CAS Unavailable ]
  • [ 55087-79-1 ]
YieldReaction ConditionsOperation in experiment
86.9% In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 10h; Inert atmosphere;
68% In diphenylether at 220℃; for 24h; Sealed tube; 2.1.1. Synthesis of 7,8,10-triphenylfluoranthene (M1) The compound M1 is synthesized as described in the literature through the Diels-Alder reaction [23]. In a typical reaction setup (0.2 g,0.56 mmol) of compound 3 and phenylacetylene (0.06 g, 0.58 mmol)were dissolved in 5 mL of diphenyl ether and kept in a sealed Teflon tubeat 220 °C for 24 h. The reaction mixture was cooled down to room temperature and the residue was diluted with hexane to precipitate the crude product. The resulting yellow solid product was purified by column chromatography using 4:1 hexane/chloroform as an eluent toafford pale greenish-blue crystalline solid. Greenish blue crystalline solid (yield 68 %). 1H NMR (400 MHz, CDCl3, ppm): δ 7.72 (dd, J = 10.1,7.3 Hz, 4H), 7.53 (dt, J = 20.3, 7.0 Hz, 3H), 7.36 (d, J = 11.0 Hz, 6H),7.30 (dd, J = 16.1, 9.0 Hz, 3H), 7.23 (d, J = 7.1 Hz, 2H), 7.17 (q, J = 6.4Hz, 3H), 6.69 (d, J = 7.1 Hz, 1H).13C NMR (100 MHz, CDCl3, ppm): δ 141.01, 140.79, 139.33, 138.22, 137.92, 136.62, 136.18, 135.92,135.71, 133.14, 131.14, 130.33, 129.96, 129.72, 129.13, 128.62,128.45, 127.80, 127.62, 127.53, 127.27, 126.63, 126.33, 123.34,122.91. HR-MS: 453.1675 [M+Na]+.
66% In diphenylether at 220℃; for 24h; Sealed tube;
at 250 - 300℃;
In diphenylether Heating;

  • 6
  • [ 641-57-6 ]
  • [ 208-96-8 ]
  • [ 7229-88-1 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: acecyclone; acenaphthylene In xylene for 16h; Heating; Stage #2: With potassium permanganate In acetone; benzene Heating; Further stages.;
at 250 - 300℃;
at 250 - 300℃;
  • 7
  • [ 82-86-0 ]
  • [ 102-04-5 ]
  • [ 641-57-6 ]
YieldReaction ConditionsOperation in experiment
96% With potassium hydroxide In ethanol; toluene at 78℃; for 1.25h; I.b Example l.b7,9-Diphenyl-6b,7-dihydrocyclopenta[a]acenaphthylen-8-oneA suspension of 16.2 g (77 mmol) of 1 ,3-diphenylpropan-2-one and 14.2 g of acenaphthoquinone in 8.2 ml of toluene and 82 ml of ethanol was heated under reflux (78°C). Subsequently, a solution of 1.35 g of KOH and 27 ml of ethanol was added dropwise within 15 minutes. The reaction mixture was stirred under reflux for a further 1 h. The reaction mixture was cooled to 0 to 5°C. The precipitated black product was filtered off with suction and washed with 3 x 100 ml of ethanol. This gave 26.2 g (yield: 96%) of the title compound. Rf (in 10:1 toluene:ethyl acetate): 0.8.
95% With potassium hydroxide In ethanol Reflux;
94% With potassium hydroxide In ethanol; toluene for 0.0833333h; Heating;
94.6% With sodium hydroxide In ethanol at 20℃; for 0.25h;
93% With potassium hydroxide In ethanol Reflux;
92.5% With potassium hydroxide In ethanol; water at 50℃; for 3h; Inert atmosphere;
92% With sodium hydroxide In ethanol; water at 60 - 80℃; for 2h; 2.1 Example 2[0109] Synthesis of exemplified compound XX- 2[0110][Chem. 13]X9 X10 XX-2 [0111] (1) Synthesis of compound X8Reagents and a solvent described below were placed in a reactor.Compound X7 : 10 g (55 mmol)Compound X2 : 12 g (55 mmol)Ethanol: 200 ml[0112] Next, the reaction solution was heated to 60° C, and then 20 ml of a 6M aqueous sodium hydroxide solution was added dropwise to the solution. After the completion of addition, the reaction solution was heated to 80° C and stirred at this temperature (80° C) for 2 hours. Next, the reaction solution was cooled to produce precipitates which were then filtered off. Next, the resultant precipitates were washed in order with water and ethanol and then dried by heating at 80° C under reduced pressure to produce 18 g of compound X8 as a dark green solid (yield: 92%).
91% With potassium hydroxide In ethanol Heating / reflux; 1 Synthesis of ,f']-4,4'7,7'-tetraphenyl}-diindeno[1,2,3-cd:1',2',3'-lm]perylene Synthesis of ,f']-4,4'7,7'-tetraphenyl}-diindeno[1,2,3-cd:1',2',3'-lm]perylene The scheme of the overall preparation of ,f']-4,4',7,7'-tetraphenyl}-diindeno[1,2,3-cd:1',2',3'-lm]perylene is exemplified in Scheme 1. This invention is directed toward the step where XV (7,12-diphenylbenzo[k]fluoranthene) is converted to XVI and XVII. Synthesis of A: A 3 L round bottom flask was charged with 1,3-diphenylacetone (200 g, 0.95 mol), acenaphthenequinone (173.3 g, 0.95 mol) and 1.4 L of ethanol and heated to near reflux. A solution of potassium hydroxide (29.3 g, 0.52 mol) in 285 ml of ethanol was added slowly to a mechanically stirred solution under nitrogen. After complete addition the reaction (black suspension) was stirred an additional thirty minutes at reflux and then cooled to 15° C. and filtered. The solids collected were washed with another 1 L of ethanol. The solids were resuspended in 1 L of methanol and filtered. Finally, the black solids collected were washed with 1 L of methanol until the filtrate was clear to yield 307.76 g of product (91% yield). Synthesis of XV: A 3 L round bottom flask with a mechanical stirrer and reflux condenser was charged with acecyclone (100 g, 0.281 mol) and 1.2 L of 1,2-dichloroethane. The reaction vessel was affixed with two addition funnels. The first contained a solution of anthranilic acid (40.40 g, 0.295 mol) in 500 ml of 1,2-dichloroethane. The second contained isoamyl nitrite (134.8 ml, 1.003 mol) in 365 ml of 1,2-dichloroethane. After bringing the reaction mixture to reflux the solutions in the two addition funnels were added dropwise and simultaneously in equal volumes to the reaction over a period of approximately 1.4 hours. The reflux condenser must be affixed in such a manner as to return solvent directly back into the reaction mixture and not into either addition funnel solution. It is critical that the addition step be performed with great caution as the reaction is highly exothermic and effervescent. If the addition is conducted to quickly a foaming eruption will occur. It is also critical the reaction temperature be at reflux prior to initiation otherwise a buildup of diazotized anthranilic acid may occur and upon thermal initiation overwhelm the reaction vessel and thermal sink. Shortly after complete addition the bubbling ceased and the reaction color changed from black to dark yellow, indicating consumption of acecyclone. The reaction was refluxed an additional hour, and the reaction mixture solvents were stripped by simple distillation until a thick yellow paste formed. These solids were triturated with 2 L of hot butanol, collected and then triturated from hot methanol and collected, washed with 1 L of methanol and dried to provide 105.42 grams of yellow solid for a 92% yield. Thin layer chromatography, 20% dichloromethane/heptane, Rf=0.8, clean blue spot. Invention, Synthesis of XVII, Version A: A 5 L round bottom flask was fixed with a mechanical stirrer and a nitrogen inlet.
90% In ethanol; water at 60 - 80℃; Alkaline aqueous solution; 1 To 200 ml of ethanol, 9.1 g (50 mmol) E4 and 10.5 g (50 mmol) E5 were added, and the resulting mixture was heated to 60°C. To the resulting mixture, 20 ml of a 5 M aqueous sodium hydroxide solution was added dropwise. Upon completion of the dropwise addition, the mixture was heated to 80°C, stirred for 2 hours, and cooled. Precipitates were filtered, washed with water and ethanol, and vacuum-dried under heating at 80°C. As a result, 16 g (yield: 90%) of dark green solid E6 was obtained.
90.05% With potassium hydroxide In ethanol Reflux;
90% With potassium hydroxide In ethanol for 0.0833333h; Reflux; Inert atmosphere;
90% With potassium hydroxide In ethanol at 78℃; for 0.25h;
90% With potassium hydroxide In ethanol for 2h; Reflux;
90% With potassium hydroxide In ethanol for 2h; Reflux; 2.4. Synthesis of 7,9-diphenyl-8H-cyclopenta[a]acenaphthylen-8-one(DCA) DCA was synthesized through reaction of acenaphthenequinone and1,3-diphenylpropan-2-one according to literature [29]. Acenaphthenequinone(5.47 g, 0.03 mol) and 1,3-diphenylpropan-2-one (6.3 g,0.03 mol) were dissolved in ethanol (60 mL) and placed in three-neck250 mL round-bottom flask equipped with refilux condenser and magneticstirrer. When the mixture solution was heat to refilux, KOH (0.8 g)which dissolved in ethanol (5 mL) solution was dropwise added via adrop funnel. The mixture immediately turned black. After dropwiseaddition of KOH ethanol solution completed, the mixture was kept inrefilux for 2 h and then cooled down to room temperature. After filtered,black precipitate was obtained. The crude product was washed withethanol several times to obtain pure product, which is purple-black solidpowder with yield of 90%. 1H NMR (CDCl3, 300 MHz, ppm): δ 8.08 (d, J= 7.1 Hz, 2H), 7.86 (m, 6H), 7.62 (t, J = 7.5 Hz, 2H), 7.56 (t, J = 7.6 Hz,4H), 7.43 (t, J = 7.0 Hz, 2H). 13C NMR (CDCl3, 100 MHz, ppm): δ 201.7,154.2, 132.1, 131.5, 131.4, 129.0, 128.6, 128.3, 127.8, 121.7, 120.9.HRMS: m/z calcd. for C27H16O, 357.1235 [M + H]+, found: 357.1260[M + H]+. Melting point: 291 C.
89% With potassium hydroxide In ethanol for 3h; Reflux;
88% With sodium hydroxide In ethanol; water at 60 - 80℃; 1 First, 9.1 g (50 mmol) of El and 10.5 g (50 iranol) of E2 were placed in 200 ml of ethanol and heated to 6O0C, and then 20 ml of a 5M aqueous sodium hydroxide solution was added dropwise. After the addition, the resultant mixture was heated to 800C, stirred for 2 hours, and then cooled. Then, the resultant precipitates were filtered off, washed with water and ethanol, and then dried by heating at 800C under reduced pressure to prepare 15.6 g (yield: 88%) of dark green solid E3. Next, 3.56 g (10 mmol) of E3 and 2.59 g (12 mmol) of E4 were placed in 50 ml of toluene and heated to 800C, and then 1.40 g (12 mmol) of isoamyl nitrite was slowly added dropwise, followed by stirring at 1100C for 3 hours. After cooling, the mixture was washed two times with 100 ml of water each time. The resultant organic layer was washed with saturated saline and dried with magnesium sulfate. Then, the solution was filtered, and the filtrate was concentrated to obtain a brownish-red liquid. The liquid was purified by column chromatography(toluene/heptane = 2 : 3) and then recrystallized with chloroform/methanol to obtain 3.96 g (yield: 88%) of an isomer mixture as yellow crystal E5.
85% With potassium hydroxide In ethanol for 2h; Reflux; 2 Preparation of dienone 2a Preparation of dienone 2a [0270] To a solution of compound 8a (l .Og, 4.76 mmol) and acenaphthylene- 1 ,2-dione (0.87g, 1 equiv) in ethanol (20ml), under reflux was added a solution of KOH (0.28g, 1 equiv) in ethanol (5ml). After addition, the reaction mixture was stirred under reflux for additional 2hrs. On cooling, dark precipitate obtained by filtration, was washed with ethanol to afford compound 2a as a dark brown solid (yield: 85%). XH NMR (400 MHz, CDC13): δ 8.09 (d, J= 7.2 Hz, 2H), 7.89 (d, J= 8.0 Hz, 2H), 7.86 (d, J= 7.6 Hz, 4H), 7.61 (t, J= 7.6 Hz, 2H), 7.55 (t, J= 7.6 Hz, 4H), 7.43 (t, J= 7.2 Hz, 2H).
85% With potassium hydroxide In ethanol Reflux; 2 Preparation of dienone 2a To a solution of compound 8a (lOg, 4.76 mmol) and acenaphthylene-1,2-dione (O.87g, 1 equiv) in ethanol (20m1), under reflux was added a solution of KOH (O.28g, 1 equiv) in ethanol (5m1). After addition, the reaction mixture was stirred under reflux for additional 2hrs. On cooling, dark precipitate obtained by filtration, was washed with ethanolto afford compound 2a as a dark brown solid (yield: 85%). ‘H NIVIR (400 MHz, CDC13):8.09 (d, J 7.2 Hz, 2H), 7.89 (d, J 8.0 Hz, 2H), 7.86 (d, J 7.6 Hz, 4H), 7.61 (t, J 7.6 Hz, 2H), 7.55 (t, J= 7.6 Hz, 4H), 7.43 (t, J 7.2 Hz, 2H)
80% With potassium hydroxide In methanol at 90℃; for 0.5h;
77% In ethanol at 85℃; for 48h; (1) Preparation of [compound-A-1] Acenaphthenequinone (30 g, 164 mmol) and 1,3-diphenyl-2-propanone (34 g, 164 mmol) were placed in ethanol (600 mL) and then potassium hydroxide (KOH) (27.6 g, 492 mmol) was added and the mixture was stirred and refluxed at 85 ° C. for 48 hours. After lowering the temperature to ordinary temperature and adding 300 mL of water, the produced solid was filtered and dried to produce [Compound A-1] (45 g, yield 77%).
72% Stage #1: acenaphthene quinone; 1,3-Diphenylpropanone In ethanol for 0.25h; Inert atmosphere; Reflux; Stage #2: With potassium hydroxide In ethanol at 0℃; for 0.25h; Inert atmosphere;
71.3% With potassium hydroxide In ethanol Reflux; 1 Synthesis of 9-Bromo-7,12-Diphenylbenzofluoranthene Exemplary Synthesis 1; Synthesis of Compound 1; Synthesis of 9,10-Diphenylanthracene-2-Boronic Acid; An amount of 6.8 g (23.7 mmol) of 2-bromoanthraquinone was suspended in a mixed solvent of 50 ml of dehydrated toluene and 50 ml of dehydrated ether and cooled to -20° C. An amount of 26.3 ml (50 mmol) of a solution of phenyllithium (1.9 mmol/ml) in butylether was added and allowed to react for six hours. Then, distilled water was added to stop the reaction. Then, the separated organic layer was applied to column chromatography to obtain a diol form. Then, the obtained diol form, 39 g (237 mmol) of potassium iodide, and 41 g (390 mmol) of sodium hypophosphite monohydrate were dissolved in acetic acid and refluxed for six hours. After cooling, the deposit was filtered and purified by column chromatography to obtain 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene. The yield was 48.3%.An amount of 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene was dissolved in dehydrated THF and cooled to -80° C. An amount of 7.9 ml (12 mmol) of a solution of n butyllithium in n hexane was added dropwise and, 40 minutes later, 3.33 g (22.8 mmol) of triethyl borate was further added. After two-hour reaction, a dilute hydrochloric acid solution was added and the mixture was allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 3.07 g (8.2 mmol) of 9,10-diphenylanthracene-2-boronic acid. The yield was 72%. Synthesis of 9-Bromo-7,12-Diphenylbenzofluoranthene; An amount of 5.9 g (32.4 mmol) of acenaphthenequinone and 7.5 g (35.7 mmol) of 1,3-diphenyl-2-propanone were suspended in 150 ml of ethanol and a solution of 2 g of potassium hydroxide in ethanol was added. After the mixture was heated to the reflux temperature, the same amount of the solution of potassium hydroxide in ethanol was further added and allowed to react for five minutes. The solid substance deposited after cooled on ice was filtered and washed with ethanol to obtain 8.24 g (23.1 mmol) of 7,9-diphenylcyclopenta[a]acenaphthylene-8-one. The yield was 71.3%.An amount of 8.24 g (23.1 mmol) of 7,9-diphenylcyclopenta[a]acenaphthylene-8-one was dissolved in 300 ml of dichloromethane and held at the reflux temperature. A solution of 5.4 g (46.2 mmol) of isoamyl nitrite in dichloromethane and a solution of 5 g (23.1 mmol) of 2-amino-5-bromobenzoic acid in dichloromethane were simultaneously added dropwise over one hour. After 12-hour reflux, methanol was added and the deposit was filtered. Then, the deposit was dissolved in xylene, refluxed for 12 hours, and purified by column chromatography to obtain 3.96 g (8.2 mmol) of 9-bromo-7,12-diphenylbenzofluoranthene. The yield was 35.5%. (Synthesis of Compound 1); An amount of 1.4 g (3.74 mmol) of 9,10-diphenylanthracene-2-boronic acid, 1.8 g (3.74 mmol) of 9-bromo-7,12-diphenylbenzofluoranthene, and 100 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 80 ml of toluene and 20 ml of ethanol. Then, 40 ml of 2M sodium carbonate solution was added and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 1.83 g (2.5 mmol) of Compound 1. The yield was 66.8%.The obtained Compound 1 was identified by the mass spectrum, infrared absorption spectrum, and NMR.
53.8% In ethanol at 75℃; for 2h; 1 1.82 g (10.0 mmol) of Compound 8, 2.62 g (12.5 mmol) of Compound 9, and 50 ml of ethanol were loaded into a 100-ml three-necked flask. In a nitrogen atmosphere, the mixture was heated to 750C, and was stirred for 2 hours . The resultant solution was cooled, and was then filtrated. The resultant black solid was washed with 10 ml..of methanol, whereby 1.91 g (53.8% yield) of Compound 10 as a blackish green solid' were obtained.
With potassium hydroxide
With potassium hydroxide; sulfuric acid 1) ethanol, reflux, 2 h, 2) acetic anhydride, reflux; Multistep reaction;
With potassium hydroxide In methanol

Reference: [1]Current Patent Assignee: BASF SE - WO2012/123888, 2012, A1 Location in patent: Page/Page column 55
[2]Location in patent: scheme or table Li, Zhanxian; Zhao, Wanying; Zhang, Yuna; Zhang, Lifeng; Yu, Mingming; Liu, Jinxia; Zhang, Hongyan [Tetrahedron, 2011, vol. 67, # 37, p. 7096 - 7100]
[3]Wehmeier, Mike; Wagner, Manfred; Muellen, Klaus [Chemistry - A European Journal, 2001, vol. 7, # 10, p. 2197 - 2205]
[4]Clevenger, Robert G.; Kumar, Bharat; Menuey, Elizabeth M.; Lee, Gene-Hsiang; Patterson, Dustin; Kilway, Kathleen V. [Chemistry - A European Journal, 2018, vol. 24, # 1, p. 243 - 250]
[5]Kumar, Shiv; Kumar, Deepak; Patil, Yogesh; Patil, Satish [Journal of Materials Chemistry C, 2015, vol. 4, # 1, p. 193 - 200]
[6]Location in patent: experimental part Kim, Soo-Kang; Jaung, Jae-Yun; Park, Jong-Wook [Molecular Crystals and Liquid Crystals, 2009, vol. 498, p. 140 - 150]
[7]Current Patent Assignee: CANON INC. - WO2012/93578, 2012, A1 Location in patent: Page/Page column 38-39
[8]Current Patent Assignee: LG DISPLAY CO.,LTD. - US2005/222417, 2005, A1 Location in patent: Page/Page column 12
[9]Current Patent Assignee: CANON INC. - EP2243761, 2010, A1 Location in patent: Page/Page column 22
[10]Location in patent: body text Li, Zhan-Xian; Zhang, Li-Feng; Zhao, Wan-Ying; Li, Xiao-Ya; Guo, Yong-Kai; Yu, Ming-Ming; Liu, Jin-Xia [Inorganic Chemistry Communications, 2011, vol. 14, # 10, p. 1656 - 1658]
[11]Location in patent: experimental part Li, Zhanxian; Zhang, Lifeng; Li, Xiaoya; Guo, Yongkai; Ni, Zhonghai; Chen, Jianhong; Wei, Liuhe; Yu, Mingming [Dyes and Pigments, 2012, vol. 94, # 1, p. 60 - 65]
[12]Wang, Hua; Liang, Yan; Wang, Yike; Xie, Huanling; Feng, Linglong; Lu, Haifeng; Feng, Shengyu [RSC Advances, 2014, vol. 4, # 33, p. 17171 - 17178]
[13]Xie, Huanling; Wang, Hua; Xu, Zhen; Qiao, Ruijing; Wang, Xuefeng; Wang, Xianming; Wu, Lianfeng; Lu, Haifeng; Feng, Shengyu [Journal of Materials Chemistry C, 2014, vol. 2, # 44, p. 9425 - 9430]
[14]Feng, Shengyu; Lu, Haifeng; Wang, Hua; Xu, Lichao [Dyes and Pigments, 2021, vol. 193]
[15]Vanel, Rémi; Berthiol, Florian; Bessières, Bernard; Einhorn, Cathy; Einhorn, Jacques [Synlett, 2011, # 9, p. 1293 - 1295]
[16]Current Patent Assignee: CANON INC. - WO2011/1741, 2011, A1 Location in patent: Page/Page column 47-48
[17]Current Patent Assignee: UNIVERSITY SYSTEM OF GEORGIA - WO2015/191616, 2015, A1 Location in patent: Paragraph 0270
[18]Current Patent Assignee: UNIVERSITY SYSTEM OF GEORGIA - WO2018/93924, 2018, A1 Location in patent: Paragraph 0294
[19]Andrew, Trisha L.; Cox, Jason R.; Swager, Timothy M. [Organic Letters, 2010, vol. 12, # 22, p. 5302 - 5305]
[20]Current Patent Assignee: LG CHEM CO.,LTD. - JP2016/505507, 2016, A Location in patent: Paragraph 0143; 0144
[21]Karunakaran, Jayachandran; Mohanakrishnan, Arasambattu K. [Organic Letters, 2018, vol. 20, # 4, p. 966 - 970]
[22]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1 Location in patent: Page/Page column 21-22
[23]Current Patent Assignee: CANON INC. - WO2007/114038, 2007, A1 Location in patent: Page/Page column 68
[24]Dilthey; ter Horst; Schommer [Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 143, p. 189,200, 201]
[25]Tsuge, Otohiko; Okita, Shigeru; Noguchi, Michihiko; Watanabe, Haruyuki [Chemistry Letters, 1981, p. 1439 - 1442]
[26]Samanta, S. R.; Mukherjee, A. K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 26 - 29]
[27]Location in patent: scheme or table Kapoor, Neha; Thomas, K. R. Justin [New Journal of Chemistry, 2010, vol. 34, # 12, p. 2739 - 2748]
  • 8
  • [ 1849-27-0 ]
  • [ 641-57-6 ]
  • [ 13730-05-7 ]
  • 9
  • [ 641-57-6 ]
  • [ 2492-23-1 ]
  • [ 60824-75-1 ]
  • 10
  • [ 96-36-6 ]
  • [ 641-57-6 ]
  • [ 112392-23-1 ]
  • [ 112392-22-0 ]
  • [ 112392-21-9 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine at 120℃; for 1h; Yield given;
76% With triethylamine at 120℃; for 1h; Yields of byproduct given;
  • 11
  • [ 641-57-6 ]
  • [ 22760-77-6 ]
  • [ 132665-89-5 ]
YieldReaction ConditionsOperation in experiment
85% In various solvent(s) at 180℃; for 0.05h;
  • 12
  • [ 641-57-6 ]
  • [ 14420-75-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
77.5% With zinc In tetrahydrofuran
  • 13
  • [ 641-57-6 ]
  • [ 1875-48-5 ]
  • [ 92050-53-8 ]
YieldReaction ConditionsOperation in experiment
80% With lead(IV) acetate In dichloromethane for 0.25h;
  • 14
  • [ 641-57-6 ]
  • [ 591-51-5 ]
  • [ 56850-20-5 ]
YieldReaction ConditionsOperation in experiment
92.6% In diethyl ether for 2h; Ambient temperature;
  • 15
  • [ 641-57-6 ]
  • [ 2130-56-5 ]
  • [ 284470-67-3 ]
YieldReaction ConditionsOperation in experiment
88% With isopentyl nitrite In 1,2-dimethoxyethane; 1,1,2-trichloroethane; dimethyl sulfoxide for 18h; Heating;
  • 16
  • [ 641-57-6 ]
  • [ 118-92-3 ]
  • [ 16391-62-1 ]
YieldReaction ConditionsOperation in experiment
98% With isopentyl nitrite In 1,2-dichloro-ethane for 1.5h; Heating;
92% With isopentyl nitrite In 1,2-dichloro-ethane for 2.4h; Heating / reflux; A 3 L round bottom flask with a mechanical stirrer and reflux condenser was charged with acecyclone (100 g, 0.281 mol) and 1.2 L of 1,2-dichloroethane. The reaction vessel was affixed with two addition funnels. The first contained a solution of anthranilic acid (40.40 g, 0.295 mol) in 500 ml of 1,2-dichloroethane. The second contained isoamyl nitrite (134.8 ml, 1.003 mol) in 365 ml of 1,2-dichloroethane. After bringing the reaction mixture to reflux the solutions in the two addition funnels were added dropwise and simultaneously in equal volumes to the reaction over a period of approximately 1.4 hours. The reflux condenser must be affixed in such a manner as to return solvent directly back into the reaction mixture and not into either addition funnel solution. It is critical that the addition step be performed with great caution as the reaction is highly exothermic and effervescent. If the addition is conducted to quickly a foaming eruption will occur. It is also critical the reaction temperature be at reflux prior to initiation otherwise a buildup of diazotized anthranilic acid may occur and upon thermal initiation overwhelm the reaction vessel and thermal sink. Shortly after complete addition the bubbling ceased and the reaction color changed from black to dark yellow, indicating consumption of acecyclone. The reaction was refluxed an additional hour, and the reaction mixture solvents were stripped by simple distillation until a thick yellow paste formed. These solids were triturated with 2 L of hot butanol, collected and then triturated from hot methanol and collected, washed with 1 L of methanol and dried to provide 105.42 grams of yellow solid for a 92% yield. Thin layer chromatography, 20% dichloromethane/heptane, Rf=0.8, clean blue spot.
89% With isopentyl nitrite In 1,4-dioxane Heating / reflux;
71.5% With isopentyl nitrite In tetrahydrofuran at 55℃; for 4h; 1 1.0 g (2.91 mmol) of Compound 10, 0.55 g (4.00 mmol) of Compound 11, 3.0 ml of isoamyl nitrite Compound 12, and 50 ml of tetrahydrofuran were loaded into a 100-ml three-necked flask. In a nitrogen atmosphere, the mixture was heated to 55°C, and was. stirred for 4 hours. After the reaction, the resultant solution was condensed and purified with a silica gel column (heptane + toluene mixed developing solvent), whereby 0.840 g (71.5% yield) of Comparative Compound 13 (whitish yellow crystal) was obtained. In addition, the structure of the compound was identified by NMR measurement.1H NMR(CDCI3^OOMHZ) ς(ppm): 7.63-7.70 (m, 10H) , 7.57(d,4H), 7.40(m,2H), 7.32(t,2H), 7.61(d,2H).

  • 17
  • [ 641-57-6 ]
  • [ 301829-08-3 ]
  • [ 373360-31-7 ]
YieldReaction ConditionsOperation in experiment
62% at 130℃; for 24h;
  • 18
  • [ 641-57-6 ]
  • [ 7567-63-7 ]
  • [ 7619-71-8 ]
YieldReaction ConditionsOperation in experiment
90% In o-xylene for 18h; Heating;
In xylene for 24h; Heating / reflux;
  • 19
  • [ CAS Unavailable ]
  • [ 641-57-6 ]
  • [ 220722-65-6 ]
YieldReaction ConditionsOperation in experiment
73% With isopentyl nitrite In tetrahydrofuran; dichloromethane Heating;
  • 20
  • [ 766-96-1 ]
  • [ 641-57-6 ]
  • [ 1013399-18-2 ]
YieldReaction ConditionsOperation in experiment
74% In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 48h; (2) Preparation of [compound-A-2] After adding [Compound A-1] (30 g, 84.2 mmol) and 1-bromo-4-ethynylbenzene (16.8 g, 92.8 mmol) in xylene (500 mL) And the mixture was stirred and refluxed at 140 ° C. for 48 hours. After lowering the temperature to ambient temperature, ethanol (300 mL) was added, and the produced solid was filtered and then dried to produce [Compound A-2] (31.3 g, yield 74%).
65% In xylene for 16h; Heating / reflux; 1 Synthesis of Intermediate 1:; To 10 mL of xylene, there were added the starting raw material 1 (5.9 g, 17 mM) and 4-bromophenyl acetylene (3 g, 17 mM) and then the resulting mixture was refluxed with heating over 16 hours. To the reaction solution, there was added methanol to thus make the resulting solids separate, followed by the removal of the solids through filtration and the washing of the solids with methylene chloride to thus give the title intermediate 1 as a yellow solid (5.6 g, yield: 65%).
  • 22
  • [ 641-57-6 ]
  • [ 107964-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: xylene / Heating 2: Br2 / CCl4
  • 23
  • [ 641-57-6 ]
  • [ 3032-92-6 ]
  • [ 1310416-68-2 ]
YieldReaction ConditionsOperation in experiment
73% In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 10h; Inert atmosphere;
66% In diphenylether at 220℃; for 24h; Sealed tube;
  • 24
  • [ 641-57-6 ]
  • [ 766-97-2 ]
  • [ 1310416-67-1 ]
YieldReaction ConditionsOperation in experiment
87% In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 10h; Inert atmosphere;
65% In diphenylether at 220℃; for 24h; Sealed tube;
  • 25
  • [ 641-57-6 ]
  • [ 15403-47-1 ]
  • [ 1231728-17-8 ]
YieldReaction ConditionsOperation in experiment
1.2% With isopentyl nitrite In toluene at 80 - 110℃; 1 Into a 200 ml round-bottomed flask, 246 mg black powder, 712 mg (2 mmol) El, and 50 ml toluene were charged, and the resulting mixture was heated to 80 °C. After 234 mg (2 mmol) of isoamyl nitrite was slowly added dropwise, stirring was conducted at HO0C for 3 hours. After cooling, the mixture was washed twice with 100 ml of water each time. The organic layer was washed with saturated saline and dried with magnesium sulfate. The resulting solution was filtered and concentrated to obtain a brown liquid. After the brown liquid had been purified by column chromatography (toluene/heptane = 1:1), recrystallization was conducted with chloroform/methanol to obtain 20 mg (yield 1.2%) of compound A3 in form of yellow crystals.[00117] The structure of the compound was confirmed by NMR spectroscopy.[00118] 1H NMR (CDCl3, 500 MHz) ς (ppm) : 7.98 (d, 2H, J = 9.5 Hz), 7.70-7.62 (m, 20H), 7.52 (d, 4H, J = 7.0 Hz), 7.51-7.20 (m, 6H), 6.50 (d, 2H, J = 7.0 Hz), 6.31 (d, 2H, J = 7.5 Hz) .[00119] The emission spectrum of a 1 x 10~5 mol/1 toluene solution of Example Compound A3 was measured with F-4500 produced by Hitachi Ltd. , and photoluminescence was measured at a 350 nm excitation wavelength. The spectrum had the maximum intensity at 459 nm
  • 26
  • [ 641-57-6 ]
  • [ 200353-88-4 ]
  • [ 1226965-82-7 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: acecyclone; ethyl 4,7-dihydro-4β,7β-ethano-2H-isoindole-1-carboxylate In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; for 72h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform at 20℃; for 21h;
  • 27
  • [ 641-57-6 ]
  • [ 205877-26-5 ]
  • [ 1242052-67-0 ]
YieldReaction ConditionsOperation in experiment
85% In o-xylene at 170℃; for 24h; Inert atmosphere;
  • 28
  • [ 641-57-6 ]
  • [ 1252591-78-8 ]
  • [ 1252591-79-9 ]
YieldReaction ConditionsOperation in experiment
80% With isopentyl nitrite In toluene at 80 - 110℃; 1; 2 Next, into 50 ml of toluene, 1.8 g (5 mmol) E6 and 1.57 g (6 mmol) E3 were added, and the resulting mixture was heated to 80°C. Then 0.82 g (7 mmol) of isoamyl nitrite was slowly added dropwise, and the resulting mixture was stirred for 3 hours at 110°C. After cooling, the mixture was washed twice with 100 ml of water each time. The organic layer was washed with saturated saline and dried with magnesium sulfate. The resulting solution was filtered and the filtrate was concentrated to obtain a brown liquid. After the brown liquid had been purified by column chromatography (toluene/heptane = 1:1), recrystallization was conducted with chloroform/methanol to obtain 2.11 g (yield 80%) of A1 in form of yellow crystals. The structure of the compound was confirmed by NMR spectroscopy: 1H NMR (CDCl3, 500 MHz) ς (ppm) : 8.19 (s, 1H), 7.88-7.64 (m, 14H), 7.37-7.28 (m, 7H), 6.54 (d, 1H, J = 7.0 Hz), 6.30 (d, 1H, J = 7.5 Hz). The emission spectrum of a 1 × 10-5 mol/l toluene solution of Example Compound A1 was measured with F-4500 produced by Hitachi Ltd., and photoluminescence was measured at a 350 nm excitation wavelength. The spectrum had the maximum intensity at 440 nm.
  • 29
  • [ 641-57-6 ]
  • [ 109-77-3 ]
  • [ 82873-06-1 ]
YieldReaction ConditionsOperation in experiment
50% With pyridine; titanium tetrachloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
  • 30
  • [ 641-57-6 ]
  • [ 20776-51-6 ]
  • [ 1260015-16-4 ]
YieldReaction ConditionsOperation in experiment
With isopentyl nitrite In toluene at 80 - 110℃; 1 First, 9.1 g (50 mmol) of El and 10.5 g (50 iranol) of E2 were placed in 200 ml of ethanol and heated to 6O0C, and then 20 ml of a 5M aqueous sodium hydroxide solution was added dropwise. After the addition, the resultant mixture was heated to 800C, stirred for 2 hours, and then cooled. Then, the resultant precipitates were filtered off, washed with water and ethanol, and then dried by heating at 800C under reduced pressure to prepare 15.6 g (yield: 88%) of dark green solid E3. Next, 3.56 g (10 mmol) of E3 and 2.59 g (12 mmol) of E4 were placed in 50 ml of toluene and heated to 800C, and then 1.40 g (12 mmol) of isoamyl nitrite was slowly added dropwise, followed by stirring at 1100C for 3 hours. After cooling, the mixture was washed two times with 100 ml of water each time. The resultant organic layer was washed with saturated saline and dried with magnesium sulfate. Then, the solution was filtered, and the filtrate was concentrated to obtain a brownish-red liquid. The liquid was purified by column chromatography(toluene/heptane = 2 : 3) and then recrystallized with chloroform/methanol to obtain 3.96 g (yield: 88%) of an isomer mixture as yellow crystal E5.
  • 31
  • [ 98026-79-0 ]
  • [ 641-57-6 ]
  • 7,11-diphenyl-8H-acenaphtho[1,2-f]isoindole-8,10(9H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In bromobenzene for 20h; Reflux;
  • 32
  • [ 641-57-6 ]
  • [ 1309373-47-4 ]
  • [ 1309373-52-1 ]
YieldReaction ConditionsOperation in experiment
92% In diphenylether at 200℃; for 24h; Inert atmosphere;
  • 33
  • [ 641-57-6 ]
  • [ 1309373-46-3 ]
  • [ 1309373-49-6 ]
YieldReaction ConditionsOperation in experiment
95% In diphenylether at 200℃; for 24h; Inert atmosphere;
  • 34
  • [ 641-57-6 ]
  • [ 1309373-46-3 ]
  • [ 1309373-50-9 ]
YieldReaction ConditionsOperation in experiment
72% In diphenylether at 200℃; for 24h; Inert atmosphere;
  • 35
  • [ 641-57-6 ]
  • [ 14235-81-5 ]
  • [ 1333998-38-1 ]
YieldReaction ConditionsOperation in experiment
65% In o-xylene for 15h; Reflux; Inert atmosphere;
55% In o-xylene for 15h; Inert atmosphere; Reflux; 4.2.3. 4-(7,10-Diphenylfluoranthen-8-yl)benzenamine (6) A stirred mixture of 4-ethynylaniline (0.70 g, 6 mmol) and 7,9-diphenyl-8H-cyclopenta[l]acenaphthylen-8-one (1.78 g, 5 mmol) in degassed o-xylene (20 mL) was refluxed for 15 h. The solvent was removed under vacuum. A pale yellow powder was purified by column chromatography (200-300 mesh), using a CH2Cl2/hexane mixture as eluent (1.23 g, 55%). 1H NMR (400 MHz; CDCl3; Me4Si): δ (ppm) 7.73 (d, 3J(H,H), J=6.8 Hz, 4H), 7.54 (m, 2H), 7.43 (m, 6H), 7.30 (m, 4H), 7.03 (d, J=8.4 Hz, 2H), 6.67 (d, J=7.2 Hz, 1H), 6.52 (d, J=8.0 Hz, 2H), 3.60 (s, 2H). 13C NMR (100 MHz, CDCl3): δ (ppm) 144.5, 140.9, 138.2, 135.1, 133.1, 130.4, 129.1, 127.2, 126.5, 123.3, 122.7, 114.5, 77.3. ESI-MS [M+1]+ 446 (100). HRMS (EI) calcd for C34H23N [M], 445.1830; found 445.1824.
  • 36
  • [ 641-57-6 ]
  • [ 103259-06-9 ]
  • [ 1326304-06-6 ]
YieldReaction ConditionsOperation in experiment
17.3% Stage #1: acecyclone; 2-(methoxycarbonyl)-6-aminobenzoic acid With isopentyl nitrite In 1,2-dichloro-ethane for 2h; Reflux; Stage #2: With sodium hydroxide In 1,2-dichloro-ethane at 20℃; Reflux; Further stages; 4.2.1. 1,2,3-Triphenyl-7H-benz[de]anthracen-7-one (1,2,3-triphenylmesobenzanthrone) (8) General procedure: A solution of tetraphenylcyclopentadienone (6, 0.200 g, 0.520 mmol) in 1,2-dichloroethane (DCE, 20 mL) was heated to a gentle reflux. A solution of isoamyl nitrite (0.50 mL, 3.7 mmol) in DCE (10 mL) was added, and the heating continued for 10 min. A suspension of 2-amino-6-(methoxycarbonyl)benzoic acid (9, 0.505 g, nominally 2.60 mmol) in DCE (30 mL) was then added in 10 equal portions, and the resulting mixture was heated at reflux for 2 h. A 2 M NaOH solution (5 mL) was added to quench the reaction, and it was cooled to room temperature. The reaction mixture was then poured into 3 M HCl (100 mL) and it was extracted with CHCl3 (50 mL). The organic layer was dried over Na2SO4, and then the solvent was stripped off. The remaining material was dissolved in toluene (100 mL), SOCl2 (2 mL) was added, and the solution was heated at reflux for 16 h. After removal of solvent, the residue was chromatographed on silica gel (solvent, 2:1 hexanes-CH2Cl2, followed by CH2Cl2) to give a yellow solid (104 mg). Recrystallization of this material from CHCl3-MeOH yielded compound 8 (97.0 mg, 0.212 mmol, 40.8%). A portion of this material (23.1 mg, 0.0504 mmol) was further purified by preparative TLC (Rf 0.52; solvent, toluene) and recrystallization from ethanol to give 8 of high purity (20.1 mg, 0.0438 mmol).
  • 37
  • [ 641-57-6 ]
  • [ 5794-88-7 ]
  • [ 1198806-84-6 ]
YieldReaction ConditionsOperation in experiment
35.5% Stage #1: acecyclone; 5-Bromo-2-aminobenzoic acid With isopentyl nitrite In dichloromethane for 13h; Reflux; Stage #2: In xylene for 12h; Reflux; 1 Exemplary Synthesis 1; Synthesis of Compound 1; Synthesis of 9,10-Diphenylanthracene-2-Boronic Acid; An amount of 6.8 g (23.7 mmol) of 2-bromoanthraquinone was suspended in a mixed solvent of 50 ml of dehydrated toluene and 50 ml of dehydrated ether and cooled to -20° C. An amount of 26.3 ml (50 mmol) of a solution of phenyllithium (1.9 mmol/ml) in butylether was added and allowed to react for six hours. Then, distilled water was added to stop the reaction. Then, the separated organic layer was applied to column chromatography to obtain a diol form. Then, the obtained diol form, 39 g (237 mmol) of potassium iodide, and 41 g (390 mmol) of sodium hypophosphite monohydrate were dissolved in acetic acid and refluxed for six hours. After cooling, the deposit was filtered and purified by column chromatography to obtain 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene. The yield was 48.3%.An amount of 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene was dissolved in dehydrated THF and cooled to -80° C. An amount of 7.9 ml (12 mmol) of a solution of n butyllithium in n hexane was added dropwise and, 40 minutes later, 3.33 g (22.8 mmol) of triethyl borate was further added. After two-hour reaction, a dilute hydrochloric acid solution was added and the mixture was allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 3.07 g (8.2 mmol) of 9,10-diphenylanthracene-2-boronic acid. The yield was 72%. Synthesis of 9-Bromo-7,12-Diphenylbenzofluoranthene; An amount of 5.9 g (32.4 mmol) of acenaphthenequinone and 7.5 g (35.7 mmol) of 1,3-diphenyl-2-propanone were suspended in 150 ml of ethanol and a solution of 2 g of potassium hydroxide in ethanol was added. After the mixture was heated to the reflux temperature, the same amount of the solution of potassium hydroxide in ethanol was further added and allowed to react for five minutes. The solid substance deposited after cooled on ice was filtered and washed with ethanol to obtain 8.24 g (23.1 mmol) of 7,9-diphenylcyclopenta[a]acenaphthylene-8-one. The yield was 71.3%.An amount of 8.24 g (23.1 mmol) of 7,9-diphenylcyclopenta[a]acenaphthylene-8-one was dissolved in 300 ml of dichloromethane and held at the reflux temperature. A solution of 5.4 g (46.2 mmol) of isoamyl nitrite in dichloromethane and a solution of 5 g (23.1 mmol) of 2-amino-5-bromobenzoic acid in dichloromethane were simultaneously added dropwise over one hour. After 12-hour reflux, methanol was added and the deposit was filtered. Then, the deposit was dissolved in xylene, refluxed for 12 hours, and purified by column chromatography to obtain 3.96 g (8.2 mmol) of 9-bromo-7,12-diphenylbenzofluoranthene. The yield was 35.5%. (Synthesis of Compound 1); An amount of 1.4 g (3.74 mmol) of 9,10-diphenylanthracene-2-boronic acid, 1.8 g (3.74 mmol) of 9-bromo-7,12-diphenylbenzofluoranthene, and 100 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 80 ml of toluene and 20 ml of ethanol. Then, 40 ml of 2M sodium carbonate solution was added and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 1.83 g (2.5 mmol) of Compound 1. The yield was 66.8%.The obtained Compound 1 was identified by the mass spectrum, infrared absorption spectrum, and NMR.
  • 38
  • [ 641-57-6 ]
  • [ 75057-62-4 ]
  • [ 1352652-21-1 ]
YieldReaction ConditionsOperation in experiment
61% With isopentyl nitrite; In xylene; at 120 - 140℃; for 3.0h; (2) Synthesis of compound X9Reagents and a solvent described below were placed in a reactor .Compound X8 : 10 g (28 mmol)Compound X4 : 17 g (56 mmol)Xylene: 100 ml[0114] Next, the reaction solution was heated to 120 C, and then 6.6 g (56 mmol) of isoamyl nitrite was slowly added dropwise to the solution. Next, the reaction solution was heated to 140 C and stirred at this temperature (140C) for 3 hours. Next, the reaction solution was cooled and then concentrated under reduced pressure to produce a brownish- red liquid. The resultant liquid was purified by column chromatography (developing solvent; toluene : heptane = 2:3) and then recrystallized with chloroform/methanol to produce 9.6 g of compound X9 as yellow crystals (yield: 61%).
  • 39
  • [ 21746-40-7 ]
  • [ 641-57-6 ]
  • [ 1352187-57-5 ]
YieldReaction ConditionsOperation in experiment
47.5% Stage #1: propylmaleimide; acecyclone In chlorobenzene at 132℃; for 3h; Stage #2: With potassium permanganate; 18-crown-6 ether In chlorobenzene at 70℃; for 2.5h; Reflux; I.c Example l.c7,1 -Diphenyl-9-propyl-9-azacyclopenta[k]fluoranthene-8,10-dioneA mixture of 5.0 g (14 mmol) of 7,9-diphenyl-6b,7-dihydrocyclopenta[a]acenaphthylen- 8-one from example l.b, 2.93 g (21.5 mmol) of n-propylmaleimide and 70 ml of chlorobenzene was heated under reflux (132°C) for 3 hours. Subsequently, the reaction mixture was cooled to 70°C and 2.9 g (18.25 mmol) of potassiumpermanganate and 4.9 g (18.25 mmol) of 18-crown-6 were added. The mixture was heated under reflux while stirring for a further 2.5 hours. The solution was filtered while still hot and the residue was washed with 3 x 10 ml of chlorobenzene. The precipitate which precipitates out of the filtrate at room temperature overnight was filtered off with suction. This gave 3.1 g (47.5% yield) of the title compound as a yellowish substance. Rf (10:1 toluene:petroleum ether) = 0.1 1.
  • 40
  • [ 641-57-6 ]
  • [ 50419-88-0 ]
  • [ 1422032-64-1 ]
YieldReaction ConditionsOperation in experiment
83% With isopentyl nitrite; In toluene; at 110℃; for 3h;Inert atmosphere; The following reagents and solvents:Compound El: 3.56 g (10 mmol) ,Compound E2 : 3.25 g (13 mmol),isoamyl nitrite: 1.52 g (13 mmol), andtoluene: 50 mLwere charged in a 100-mL recovery flask.[0137] Then, the reaction solution was heated to 110C and stirred at this temperature (110C) for 3 hr under anitrogen gas flow. After completion of the reaction, the organic layer was washed with 50 mL of water twice and then with a saturated saline solution and was dried overmagnesium sulfate. The resulting solution was filtered, and the filtrate was concentrated to obtain a dark brownsolution. This solution was purified by columnchromatography (chloroform : heptane = 1:4), followed by recrystallization from chloroform/methanol to obtain 4.3 g (yield: 83%) of Compound E3 as yellow crystals.
  • 41
  • [ 641-57-6 ]
  • [ CAS Unavailable ]
  • [ 1448460-38-5 ]
YieldReaction ConditionsOperation in experiment
41% In 5,5-dimethyl-1,3-cyclohexadiene at 230℃; for 20h; Inert atmosphere; Autoclave;
40% In 5,5-dimethyl-1,3-cyclohexadiene at 230℃; for 20h; Inert atmosphere; 2.2.1. Synthesis of BFMPS BFMPS was prepared by the DielseAlder reaction (Scheme 1).Typically, 5.30 g (15 mmol) of 7,9-diphenyl-cyclopenta[a]acenaphthylen-8-one and 1.70 g (10 mmol) of diethynylmethylphenylsilanewere dissolved in 30 mL of xylene in a sealed stainless steel reactor.The reaction was run for 20 h at 230 C under nitrogen. Afterward,xylene was removed in a vacuum. The product was purified by silicagel column chromatography. The desired product was a yellow solidand the yield was 40%.
40% In 5,5-dimethyl-1,3-cyclohexadiene at 230℃; for 20h; Inert atmosphere;
  • 42
  • [ 641-57-6 ]
  • [ 1066-54-2 ]
  • [ 1246675-16-0 ]
YieldReaction ConditionsOperation in experiment
57% In 5,5-dimethyl-1,3-cyclohexadiene at 230℃; for 20h; Autoclave; Inert atmosphere;
55% In 5,5-dimethyl-1,3-cyclohexadiene at 230℃; for 20h; Sealed tube; Inert atmosphere;
  • 43
  • [ 641-57-6 ]
  • [ 1675-60-1 ]
  • [ 1610362-50-9 ]
YieldReaction ConditionsOperation in experiment
46% In 5,5-dimethyl-1,3-cyclohexadiene at 230℃; for 20h; Autoclave; Inert atmosphere;
  • 44
  • [ 641-57-6 ]
  • [ 1675-57-6 ]
  • [ 1610362-51-0 ]
YieldReaction ConditionsOperation in experiment
35% In 5,5-dimethyl-1,3-cyclohexadiene at 230℃; for 20h; Inert atmosphere; Autoclave;
30% In diphenylether at 230℃; for 8h; Inert atmosphere;
  • 45
  • [ 641-57-6 ]
  • [ 1507465-00-0 ]
  • [ 1507465-03-3 ]
YieldReaction ConditionsOperation in experiment
84.9% In o-xylene at 150℃; for 24h; Inert atmosphere;
  • 46
  • [ 206768-21-0 ]
  • [ 641-57-6 ]
  • [ 2568961-31-7 ]
YieldReaction ConditionsOperation in experiment
62.8% In o-xylene at 150℃; for 24h; Inert atmosphere; General procedure: 5-(3',6'-diphenyl-[1,1':2',1''-terphenyl]-4'-yl)thiophene-2-carbaldehyde (1). 5-Ethynylthiophene-2-carbaldehyde (0.36 g, 2.64 mmol) and 2,3,4,5-tetraphenylcyclopenta-2,4-dienone (0.92 g, 2.40 mmol) were dissolved in o-xylene (70 mL) under an argon atmosphere, and the resultant mixture was heated for 24 h at 150 °C. After the mixture was cooled to room temperature, ethanol (100 mL) was added. The precipitate was filtered, washed with ethanol (150 mL), and dried in vacuum. Following column chromatography (petroleum ether: CH2Cl2 = 1:1) on silica gel, 1 was obtained as a white solid. Yield: 0.81 g (68.6%). 5-(1,4-Diphenyltriphenylen-2-yl)thiophene-2-carbaldehyde (2) and 5-(7,10-diphenylfluoranthen-8-yl)thiophene-2-carbaldehyde (3) were synthesized with the similar procedure as for 1 except that different ketones were used as starting materials as shown in Scheme 1. (3) Yield: 0.90g (62.8%). 1H NMR (400MHz, CDCl3) δ 9.76 (s, 1H), 7.76 (dd, J=11.0, 8.2Hz, 2H), 7.72-7.66 (m, 2H), 7.62-7.48 (m, 8H), 7.48-7.42 (m, 2H), 7.39 (t, J=7.6Hz, 1H), 7.34-7.27 (m, 2H), 6.87 (d, J=3.9Hz, 1H), 6.57 (d, J=7.2Hz, 1H). MS (ESI+): m/z 465.5 (MH+). Calcd for C33H20OS: 464.58.
  • 47
  • [ 641-57-6 ]
  • [ 59745-28-7 ]
  • [ 1802327-28-1 ]
YieldReaction ConditionsOperation in experiment
68% In diphenylether at 220℃; for 24h; Sealed tube;
  • 48
  • [ 404906-09-8 ]
  • [ 641-57-6 ]
  • [ 1802327-29-2 ]
YieldReaction ConditionsOperation in experiment
73% In diphenylether at 220℃; for 24h; Sealed tube;
  • 49
  • [ 641-57-6 ]
  • [ 79887-17-5 ]
  • [ 1835681-24-7 ]
YieldReaction ConditionsOperation in experiment
70% In diphenylether at 220℃; for 24h; Sealed tube;
  • 50
  • [ 641-57-6 ]
  • [ 34296-24-7 ]
  • [ 1429205-63-9 ]
YieldReaction ConditionsOperation in experiment
60% In diphenylether at 220℃; for 24h; Sealed tube;
  • 51
  • [ 641-57-6 ]
  • [ 1263291-41-3 ]
  • [ 201230-82-2 ]
  • C36H30O [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In dichloromethane at 20℃; 1 Separate solutions of pure TPCPD (1) and pure exo-BCN (6a) (>95-98% by 1H- NMR) were prepared in HPLC-grade methanol (acetonitrile, 1 ,2-dichloroethane, dioxane) at room temperature. The stability of TPCPD in methanol (25 μΜ) was examined by monitoring its absorption maximum at 335 nm. The solutions containing TPCPD (1, 50 μΜ, 400 μ) and 18-fold excess of exo-BCN (6a, 900 μΜ, 400 μ) were added into quartz cuvettes, thoroughly mixed and sealed with a PTFE cap. All kinetic runs were triplicates. Curve fitting was operated in Prism5 software. [0265] The reaction between 1 and 6a (Scheme 8) leads to significant changes in the UV- Vis spectrum of TPCPD (30) due to its conversion to the cyclization product 31 (Figure la). Therefore, the reaction can be easily monitored. The reaction performed in dry methanol and the rate constant for the reaction between TPPD and BCN was found to be 0.50 M'V1 (Figure lb). Gas bubble formation was readily apparent, suggesting the release of CO as a byproduct. [0266] It was observed that the reaction rate between TPCPD and BCN was moderately sensitive to the reaction solvent. Methanol, acetonitrile, 1 ,2-dichloroethene (DCE), and dioxane were chosen for the kinetic studies. The reaction appears to be faster in polar solvents than in nonpolar solvents. For example, half-life (ti/2) of the reaction is 99 min in acetonitrile (Table 1), which is faster than in DCE (130 min), and in dioxane (282 min). The reaction in methanol was observed to be faster than in acetonitrile, which clearly indicates that the protic solvent has an enhancing effect on the reaction rate. In order to utilize the reaction under physiological conditions, the reaction rate was measured at physiological temperature, 37°C. The results are shown in Table 1. Table 1. Second order rate constants of TPCPD with BCN in different solvents. * All half-life va ues were determined for exo-BCN at 450 μΜ (6a). [0267] From Table 1 , it is observed that the second order rate constant at 37°C increased about 2 fold compared to the rate at room temperature, 23°C.
  • 52
  • [ 641-57-6 ]
  • [ 4863-90-5 ]
  • C138H84 [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% In diphenylether at 200℃; for 24h;
  • 53
  • [ 641-57-6 ]
  • [ 766-81-4 ]
  • [ 1610789-96-2 ]
YieldReaction ConditionsOperation in experiment
69% In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 48h; (3) Preparation of [compound-A-3] After adding [Compound A-1] (30 g, 84.2 mmol) and 1-bromo-4-ethynylbenzene (16.8 g, 92.8 mmol) in xylene (50 mL) And the mixture was stirred and refluxed at 140 ° C. for 48 hours. After lowering the temperature to room temperature and adding ethanol (300 mL), the produced solid was filtered and then dried to produce [Compound A-3] (29.7, yield 69%).
  • 54
  • [ 641-57-6 ]
  • [ 38215-38-2 ]
  • C68H42 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diphenylether; at 260℃; for 8h;Inert atmosphere; Compound A (2.21 g, 11 mmol), compound B (7.80 g, 22 mmol) and diphenyl ether (100 mL) were added to a 250-mL reaction flask.Nitrogen emptying 3 times, heating up to 260 , to maintain this temperature, the reaction 8 hours,TLC and HPLC detection of compound B complete reaction.During the reaction, the color change of the reaction liquid changed from black to yellow.Reaction after treatment: stop heating, cooling to 20 , adding methanol (100mL), stirring 2h precipitation of solid,The filter cake was washed with methanol and dried in vacuo to give the crude product.The crude product was added with ethyl acetate to give yellow compound 1 (4.32 g, 46% yield,HPLC purity 93.58%).Vacuum sublimation (360 C, 2 x 10-5 torr, 8 hours) to give a pale yellow solid powder,Purity 99.5%. see picture 1.
  • 55
  • [ 31366-25-3 ]
  • [ 641-57-6 ]
  • [ 55087-78-0 ]
YieldReaction ConditionsOperation in experiment
76% In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Inert atmosphere; Reflux;
  • 56
  • [ 641-57-6 ]
  • [ 20776-50-5 ]
  • [ 1198806-84-6 ]
YieldReaction ConditionsOperation in experiment
63% With isopentyl nitrite In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Inert atmosphere; Reflux; 1 Example 1: Synthesis of Intermediate A 1 L three-necked flask is placed in 17.8 g 7,9-diphenyl-8H-cyclopenta[a]acenaphthylen-8-one (7,9-diphenyl-8H-cyclopenta[a]acenaphthylen-8-one) , 12.9 grams of 2-amino-4-bromobenzoic acid (2-amino-4-bromobenzoic acid), and 14.6 grams of isopentyl nitrite (Isopentyl nitrite) dissolved in 250 mL of xylene, placed under a nitrogen system The reaction was heated and refluxed for 6 hours. After cooling, the organic layer was separated, and the aqueous layer was extracted twice with 300 ml of toluene. The organic layers were combined and concentrated. The concentrated solution was forced out by adding methanol, filtered to obtain a white solid, and dried to obtain intermediate A product 31 G, the yield is 63%.
  • 57
  • [ 22612-93-7 ]
  • [ 17694-87-0 ]
  • [ 641-57-6 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 9,10-dihydro-9,10-ethanoanthracene-11,12-dione; 1,8-bis-(phenylethynyl)naphthalene With bis(cycloocta-1,5-diene)rhodium (I) tetrafluoroborate In dichloromethane at 20℃; for 9h; Inert atmosphere; Sealed tube; Irradiation; Stage #2: With triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere; Sealed tube; 6. 1. Procedure for the [Rh(cod)2]BF4-catalyzed cyclocarbonylation of 2 and anthracene α-diketone (1). General procedure: [Rh(cod)2]BF4 (10.15 mg, 0.025 mmol), diyne 2 (0.50 mmol) and 1 (118.14 mg, 0.5 mmol) were added to a 5 mL two-necked flask, and 5 mL of anhydrous CH2Cl2 was added with stirring. Three freezepump-thaw cycles, in which N2 was charged, were performed by using liquid nitrogen. The reaction was maintained as a close system (internal volume: 10 mL). After allowing the mixture to reach room temperature, the solution was irradiated with a 5W Blue LED (480 nm). In the experiments involving light-irradiation, the Blue LED was placed at a distance of 1 cm from the reaction vessel, and the entire reaction vessel and the light source was covered with a box. After 9 hours, the irradiation was stopped and PPh3 (26.4 mg, 0.1 mmol, 4 eq to Rh) was added. After 1 h, the stirring was stopped and the reaction vessel was opened. The resulting solution was examined by TLC measurements, transferred to an eggplant-shaped flask, and concentrated on a flash evaporator. Purification by silica gel column chromatography gave the cyclopentadienone derivative 3.
Same Skeleton Products
Historical Records