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Chemistry
Organic Building Blocks
Aryls
naphthoate
Ethyl 2-naphthoate
Chemistry
Organic Building Blocks
Aryls
Esters Benzene Compounds
naphthoate
naphthyl

[ CAS No. 3007-91-8 ] {[proInfo.proName]}

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Product Details of [ 3007-91-8 ]

CAS No. :3007-91-8 MDL No. :MFCD00016811
Formula : C13H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HQKSINSCHCDMLS-UHFFFAOYSA-N
M.W : 200.23 Pubchem ID :76363
Synonyms :

Safety of [ 3007-91-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3007-91-8 ]

* 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 [ 3007-91-8 ]

[ 3007-91-8 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 3007-91-8 ]
  • [ 613-46-7 ]
YieldReaction ConditionsOperation in experiment
74% General procedure: NaOtBu (98% purity, 353 mg, 3.6 mmol) was dried by a vacuum pump for 30 min at room temperature. To a solution of NaOtBu in THF (3 mL) was added DIBAL-H (1.04 M, 3.27 mL, 3.4 mmol) at 0 C under argon atmosphere and the obtained mixture was stirred for 1 h at room temperature. Then, ethyl benzoate (150.06 mg, 2.0 mmol) in THF (4 mL) was added to the solution at 0 C, and the obtained mixture was stirred for 4 h. Finally, aq NH3 (concentration: 28.0%-30.0%, 4 mL) and I2 (2.08 g, 4.1 equiv) were added at 0 C, and the obtained mixture was stirred for 3 h at room temperature. Then the reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent under reduced pressure, the residue was treated with flash short column chromatography on silica gel (eluent: hexane/ethyl acetate=9:1) to afford benzonitrile (156.7 mg, 76% yield)
Reference： [1]Tetrahedron,2011,vol. 67,p. 7956 - 7962
[2]Bulletin de la Societe Chimique de France,1918,vol. <4> 23,p. 237
    Annales de Chimie (Cachan, France),1920,vol. <9> 13,p. 220
[3]Bulletin de la Societe Chimique de France,1918,vol. <4> 23,p. 237
    Annales de Chimie (Cachan, France),1920,vol. <9> 13,p. 220
[4]European Journal of Organic Chemistry,2013,p. 5886 - 5892
  • 2
  • [ 3007-91-8 ]
  • [ 93-08-3 ]
  • [ 51583-97-2 ]
YieldReaction ConditionsOperation in experiment
96% With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux; 3 <Synthesis of Intermediate 73-10> After dissolving 47.12g (235.34mmol) of Intermediate 73-8 and 40.06g (253.34mmol) of Intermediate 73-9 in 2L of xylene, 12.71g (253.34mmol) of NaOMe was added and heated to reflux for 12 hours and stirred. After completion of the reaction, the mixture was cooled to room temperature, 300 ml of 1N HCl was added, and the organic layer was extracted and distilled. After the column, 73.28g of the intermediate 73-10 was obtained in a yield of 96%
With sodium amide
With sodium methylate In diethyl ether at 20℃; for 48h;
With sodium hydride In tetrahydrofuran at 67℃; for 24h; Inert atmosphere; Reflux;

Reference： [1]Current Patent Assignee: NANJING TOPTO SEMICONDUCTOR MATERIAL CO LTD - KR2020/108161, 2020, A Location in patent: Paragraph 0210; 0231-0234
[2]Current Patent Assignee: EASTMAN KODAK CO - US2865747, 1955, A
[3]Uekawa, Masahiro; Miyamoto, Yasuo; Ikeda, Hitoshi; Kaifu, Katsuaki; Nakaya, Tadao [Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 9, p. 2253 - 2258]
[4]Yamada, Tohru; Nagata, Takushi; Sugi, Kiyoaki D.; Yorozu, Kiyotaka; Ikeno, Taketo; Ohtsuka, Yuhki; Miyazaki, Daichi; Mukaiyama, Teruaki [Chemistry - A European Journal, 2003, vol. 9, # 18, p. 4485 - 4509]
[5]Sun, Lining; Qiu, Yannan; Liu, Tao; Peng, Hongshang; Deng, Wei; Wang, Zhijuan; Shi, Liyi [RSC Advances, 2013, vol. 3, # 48, p. 26367 - 26375]
  • 3
  • [ 64-17-5 ]
  • [ 93-09-4 ]
  • [ 3007-91-8 ]
YieldReaction ConditionsOperation in experiment
99% With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h; Esterification; General Procedure General procedure: Carboxylic acid 1 (1.0 mmol, 1.0 equiv), alcohol 2 (2.0 mmol, 2.0 equiv), DIPEA (3.0 mmol, 3.0 equiv) and DCE (the reaction mixture was diluted to 0.2 M) were added to an oven-dried 25 mL reaction flask equipped with a stir bar and sealed with a rubber stopper. SO2F2 gas was introduced into the stirred reaction mixture by slowly bubbling from a balloon [the balloons were made from low-density polyethylene (LDPE) which it not reactive with SO2F2]. The reaction mixture was stirred at room temperature for 5 h. After the reaction was completed, the reaction mixture was directly concentrated under vacuum and was purified by column chromatography on silica gel using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 3. To confirm the amount of SO2F2 consumed in this transformation, 4-biphenylcarboxylic acid (1a) (10 mmol, 1.0 equiv), EtOH (2a) (20 mmol, 2.0 equiv), DIPEA (30 mmol, 3 equiv) and DCE (the reaction mixture was diluted to 0.2 M) were added to an oven-dried 100 mL reaction flask equipped with a stir bar and sealed with a rubber stopper. A balloon filled with SO2F2 gas was weighed before introduction of the SO2F2 gas into the stirring reaction mixture by slow bubbling at room temperature. After the reaction complete, the SO2F2 balloon was weighed again to measure the difference in weight. It was calculated that the SO2F2 consumption was about 3.26 g (31.9 mmol, 3.2 equiv) in this particular reaction (some of the gas dissolved in the DCE solvent can be considered as unreacted but consumed). The corresponding ester product 3a was obtained in 98% yield after work-up.
90% With thionyl chloride for 6h; Reflux; 1.1 Synthesis of 1a Into a 250 mL reaction flask, 58 mmol of 2-naphthoic acid and 40 mL of ethanol were charged, followed by heating under reflux, 2 mL of thionyl chloride was added dropwise and the mixture was refluxed for 6 hours. The reaction solution was then spin-dried to give a colorless liquid product in a yield of 90%
84% With sulfuric acid Reflux;
75% With sulfuric acid for 10h; Reflux;
62% at 350℃; for 0.0666667h; Supercritical conditions; Flow reactor; High pressure;
With sulfuric acid
With sulfuric acid In benzene
With sulfuric acid
With sulfuric acid Reflux;
With sulfuric acid for 2h; Reflux; 4.4. General procedure for the synthesis of 2-naphthoic and 3-phenylpropanoic acid hydrazides (33g and 33h) General procedure: To a solution of the corresponding carboxylic acid derivative (34) or (35) (3 mmol) in 10 mL of ethanol was added a catalytic amount of concentrated H2SO4 and the mixture was refluxed for 2 h, when analysis by TLC indicated the end of the reaction. Then, 3 mL of 80% hydrazine monohydrate was added. The reaction mixture was maintained under reflux for 3 h, when TLC indicated the total consumption of the ester intermediate. The media was poured onto ice and the resulting precipitate was filtered out, affording the corresponding acylhydrazide derivatives (33g) and (33h) as described next.
With sulfuric acid
With thionyl chloride at 130℃; for 12h;
With sulfuric acid for 12h; Reflux;
With sulfuric acid Reflux;
With sulfuric acid Reflux; - Route B (R1 = aryl) General procedure: Note: hydrazine and carbon disulphide used during this procedure have to be handled withcaution.The carboxylic compound was first converted into its ethyl ester by refluxing in absoluteethanol in the presence of a few drops of H2SO4. The ester was then treated overnight withhydrazine hydrate (2 to 4 equiv.) without solvent at 120 °C. Evaporation of excess hydrazineyielded the corresponding hydrazide compound. The hydrazide, solubilized in absolute ethanol,was treated with CS2 (5 equiv.) in the presence of KOH (1.7 equiv.) at 85 °C for 3 h. Water wasadded and pH was adjusted to 2-3 with 1N HCl. The formed precipitate was collected byfiltration and washed with water, yielding the 1,3,4-oxadiazol-thione, which was used withoutfurther purification. Finally, the preceding compound was treated with hydrazine hydrate (10equiv.) in absolute ethanol at 100 °C overnight in a sealed tube. After evaporation of excesshydrazine, the residue was purified on a silica gel column to yield the final compound.
With sulfuric acid for 5h; Reflux; - General synthetic procedure for the preparation of hydrazides R1-CO-NHNH2 General procedure: To a solution of the acid R1-CO2H in EtOH was added concentrated H2SO4 (2 equiv.) and the reaction mixture was refluxed for 5 h. After cooling to room temperature, water was added and the solution was neutralized with Na2CO3. The aqueous phase was extracted twice with EtOAc. The organic phases were combined, dried over MgSO4, filtered and evaporated under vacuum to yield the ethyl ester, which was used without necessity of purification.

Reference： [1]Qin, Hua-Li; S Alharbi, Njud; Wang, Shi-Meng [Synthesis, 2019, vol. 51, # 20, p. 3901 - 3907]
[2]Current Patent Assignee: CHENGZHI SHAREHOLDING CO., LTD. - CN103896852, 2016, B Location in patent: Paragraph 0082-0084
[3]Kiehl, Jonathan; Hochdörffer, Tim; Carrella, Luca M.; Schünemann, Volker; Nygaard, Mathilde H.; Overgaard, Jacob; Rentschler, Eva [Inorganic Chemistry, 2022, vol. 61, # 7, p. 3141 - 3151]
[4]Location in patent: experimental part Luňák Jr., Stanislav; Havel, Lukáš; Vyňuchal, Jan; Horáková, Petra; Kučerík, Jiří; Weiter, Martin; Hrdina, Radim [Dyes and Pigments, 2010, vol. 85, # 1-2, p. 27 - 36]
[5]Adeyemi, Ahmed; Bergman, Joakim; Brånalt, Jonas; Sävmarker, Jonas; Larhed, Mats [Organic Process Research and Development, 2017, vol. 21, # 7, p. 947 - 955]
[6]Perkin [Journal of the Chemical Society, 1896, vol. 69, p. 1241][Journal of the Chemical Society, 1900, vol. 77, p. 278]
[7]Arrowsmith,G.B. et al. [Journal of the Chemical Society, 1965, p. 2072 - 2078]
[8]Location in patent: scheme or table Ke, Shao-Yong; Qian, Xu-Hong; Liu, Feng-Yi; Wang, Ni; Yang, Qing; Li, Zhong [European Journal of Medicinal Chemistry, 2009, vol. 44, # 5, p. 2113 - 2121] Location in patent: scheme or table Ke, Shaoyong; Liu, Fengyi; Wang, Ni; Yang, Qing; Qian, Xuhong [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 332 - 335]
[9]Location in patent: scheme or table Hu, Yang; Lu, Xiang; Chen, Ke; Yan, Ru; Li, Qing-Shan; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 903 - 909]
[10]Location in patent: experimental part Carvalho, Samir A.; Feitosa, Larisse O.; Soares, Marcio; Costa, Thadeu E.M.M.; Henriques, Maria G.; Salomao, Kelly; De Castro, Solange L.; Kaiser, Marcel; Brun, Reto; Wardell, James L.; Wardell, Solange M.S.V.; Trossini, Gustavo H.G.; Andricopulo, Adriano D.; Da Silva, Edson F.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 512 - 521]
[11]Du, Qian-Ru; Li, Dong-Dong; Pi, Ya-Zhou; Li, Jing-Ran; Sun, Jian; Fang, Fei; Zhong, Wei-Qing; Gong, Hai-Bin; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297]
[12]Harikishore, Amaravadhi; Leow, Min Li; Niang, Makhtar; Rajan, Sreekanth; Pasunooti, Kalyan Kumar; Preiser, Peter Rainer; Liu, Xuewei; Yoon, Ho Sup [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 11, p. 1097 - 1101]
[13]Kim, Jinwoo; Chang, Sukbok [Angewandte Chemie - International Edition, 2014, vol. 53, # 8, p. 2203 - 2207][Angew. Chem., 2014, vol. 126, # 8, p. 2235 - 2239,5]
[14]Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985]
[15]Baud, Damien; Bebrone, Carine; Becker, Katja; Benvenuti, Manuela; Cerboni, Giulia; Chelini, Giulia; Cutolo, Giuliano; De Luca, Filomena; Docquier, Jean-Denis; Feller, Georges; Fischer, Marina; Galleni, Moreno; Gavara, Laurent; Gresh, Nohad; Kwapien, Karolina; Legru, Alice; Mangani, Stefano; Mercuri, Paola; Pozzi, Cecilia; Sannio, Filomena; Sevaille, Laurent; Tanfoni, Silvia; Verdirosa, Federica; Berthomieu, Dorothée; Bestgen, Benoît; Frère, Jean-Marie; Hernandez, Jean-François [European Journal of Medicinal Chemistry, 2020, vol. 208]
[16]Gavara, Laurent; Legru, Alice; Verdirosa, Federica; Sevaille, Laurent; Nauton, Lionel; Corsica, Giuseppina; Mercuri, Paola Sandra; Sannio, Filomena; Feller, Georges; Coulon, Rémi; De Luca, Filomena; Cerboni, Giulia; Tanfoni, Silvia; Chelini, Giulia; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [Bioorganic Chemistry, 2021, vol. 113]
  • 4
  • [ 3007-91-8 ]
  • [ 1592-38-7 ]
YieldReaction ConditionsOperation in experiment
79% With sodium tetrahydroborate; <i>N</i>,<i>N</i>-dimethyl-aniline; zinc(II) chloride In tetrahydrofuran for 2h; Heating;
72% With 15-crown-5; (1-(2-(2,3-diisopropyl-1-methylguanidino)ethyl)-3-mesityl-1,3-dihydro-2H-imidazol-2-ylidene)copper(I) chloride; hydrogen; sodium t-butanolate In 1,4-dioxane at 60℃; for 24h; Inert atmosphere; Large scale;
With lithium aluminium tetrahydride
Multi-step reaction with 2 steps 1: lithium tert-butoxide / tetrahydrofuran / 12 h / 0 - 20 °C 2: sodium hydroxide / water / 1 h / 20 °C

Reference： [1]Yamakawa, Tomio; Masaki, Mitsuo; Nohira, Hiroyuki [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 9, p. 2730 - 2734]
[2]Kaicharla, Trinadh; Ngoc, Trung Tran; Teichert, Johannes F.; Tzaras, Dimitrios-Ioannis; Zimmermann, Birte M. [Journal of the American Chemical Society, 2021, vol. 143, # 40, p. 16865 - 16873]
[3]Burgstahler,A.W. et al. [Journal of the Chemical Society, 1963, p. 4986 - 4989]
[4]Kim, Jea Ho; Jaladi, Ashok Kumar; Kim, Hyun Tae; An, Duk Keun [Bulletin of the Korean Chemical Society, 2019, vol. 40, # 10, p. 971 - 975]
  • 5
  • [ 13209-15-9 ]
  • [ 140-88-5 ]
  • [ 3007-91-8 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 3013 - 3018
  • 6
  • [ 3007-91-8 ]
  • [ 75-05-8 ]
  • [ 613-57-0 ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydride In toluene at 90℃; for 24h;
71% With naphthalene; potassium In toluene at 5 - 10℃; for 1.5h; ultrasonic irradiation;
61% Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: ethyl-2-naphthoate In tetrahydrofuran; hexane at -78℃; for 2h;
With potassium 2-methylbutan-2-olate In tetrahydrofuran; toluene at 20℃; for 0.333333h; Inert atmosphere;
With sodium hydride In toluene at 90℃; for 7h; Inert atmosphere;

Reference： [1]Baraldi, Pier Giovanni; Romagnoli, Romeo; Pavani, Maria Giovanna; Del Carmen Nuñez, Maria; Tabrizi, Mojgan Aghazadeh; Shryock, John C.; Leung, Edward; Moorman, Allan R.; Uluoglu, Canan; Iannotta, Valeria; Merighi, Stefania; Borea, Pier Andrea [Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 794 - 809]
[2]Gao, Yang; Wang, Hui; Xu, Minghua; Lian, Hongzhen; Pan, Yi; Shi, Yaozeng [Organic Preparations and Procedures International, 2001, vol. 33, # 4, p. 351 - 356]
[3]Xu, Kai; Liu, Hao; Hou, Yilin; Shen, Jiefeng; Liu, Delong; Zhang, Wanbin [Chemical Communications, 2019, vol. 55, # 88, p. 13295 - 13298]
[4]Vazquez-Villa, Henar; Reber, Stefan; Ariger, Martin A.; Carreira, Erick M. [Angewandte Chemie - International Edition, 2011, vol. 50, # 38, p. 8979 - 8981]
[5]Wang, Kai-Kai; Wang, Pan; Ouyang, Qin; Du, Wei; Chen, Ying-Chun [Chemical Communications, 2016, vol. 52, # 74, p. 11104 - 11107]
  • 7
  • [ 532-02-5 ]
  • [ 3007-91-8 ]
Reference： [1]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
    Chemische Berichte,1875,vol. 8,p. 1278
[2]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
    Chemische Berichte,1875,vol. 8,p. 1278
  • 8
  • [ 3007-91-8 ]
  • [ 39627-84-4 ]
YieldReaction ConditionsOperation in experiment
99% With hydrazine hydrate In ethanol Reflux;
85% With hydrazine hydrate In ethanol Reflux;
0.9 g (48%) With hydrazine hydrate In ethanol 1 Example 1 STR4 5-Naphthalen-2-yl-3H-[1,3,4]oxadiazole-2-thione To a solution of 2-naphthyl carboxylic acid ethyl ester (2.0 g, 9.99 mmol) in absolute ethanol (30 ml) was added hydrazine hydrate (4.85 ml, 99.9 mmol) and the reaction mixture was heated at reflux temperature for 72 h. The reaction mixture was cooled and the precipitate was filtered off, washed with 96% ethanol (2*10 ml) and diethyl ether (3*10 ml), dried in vacuo at 50° C. which afforded 0.9 g (48%) of naphthalene-2-carboxylic acid hydrazide as a solid.
With hydrazine hydrate In ethanol for 17h; Heating;
With hydrazine hydrate for 8h; Reflux;
With hydrazine In ethanol for 16h; Reflux; Inert atmosphere;
With hydrazine hydrate
With hydrazine hydrate In ethanol for 3h; Reflux; 4.4. General procedure for the synthesis of 2-naphthoic and 3-phenylpropanoic acid hydrazides (33g and 33h) General procedure: To a solution of the corresponding carboxylic acid derivative (34) or (35) (3 mmol) in 10 mL of ethanol was added a catalytic amount of concentrated H2SO4 and the mixture was refluxed for 2 h, when analysis by TLC indicated the end of the reaction. Then, 3 mL of 80% hydrazine monohydrate was added. The reaction mixture was maintained under reflux for 3 h, when TLC indicated the total consumption of the ester intermediate. The media was poured onto ice and the resulting precipitate was filtered out, affording the corresponding acylhydrazide derivatives (33g) and (33h) as described next.
With hydrazine hydrate In ethanol Reflux;
With hydrazine In ethanol at 130℃; for 12h;
With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube;
With hydrazine In ethanol at 80℃;
With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube; - Route B (R1 = aryl) General procedure: Note: hydrazine and carbon disulphide used during this procedure have to be handled withcaution.The carboxylic compound was first converted into its ethyl ester by refluxing in absoluteethanol in the presence of a few drops of H2SO4. The ester was then treated overnight withhydrazine hydrate (2 to 4 equiv.) without solvent at 120 °C. Evaporation of excess hydrazineyielded the corresponding hydrazide compound. The hydrazide, solubilized in absolute ethanol,was treated with CS2 (5 equiv.) in the presence of KOH (1.7 equiv.) at 85 °C for 3 h. Water wasadded and pH was adjusted to 2-3 with 1N HCl. The formed precipitate was collected byfiltration and washed with water, yielding the 1,3,4-oxadiazol-thione, which was used withoutfurther purification. Finally, the preceding compound was treated with hydrazine hydrate (10equiv.) in absolute ethanol at 100 °C overnight in a sealed tube. After evaporation of excesshydrazine, the residue was purified on a silica gel column to yield the final compound.
With hydrazine hydrate In ethanol at 100℃; Sealed tube; General procedure: The ester was then solubilized in EtOH and treated with hydrazine, hydrate (5 equiv.). The mixture was refluxed overnight and solvents were evaporated. Diethyl ether was added and the formed precipitate was filtered and washed with the same solvent to yield the expected hydrazide compound as a powder.

Reference： [1]Kiehl, Jonathan; Hochdörffer, Tim; Carrella, Luca M.; Schünemann, Volker; Nygaard, Mathilde H.; Overgaard, Jacob; Rentschler, Eva [Inorganic Chemistry, 2022, vol. 61, # 7, p. 3141 - 3151]
[2]Location in patent: scheme or table Hu, Yang; Lu, Xiang; Chen, Ke; Yan, Ru; Li, Qing-Shan; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 903 - 909]
[3]Current Patent Assignee: NOVO NORDISK A/S - US5958957, 1999, A
[4]Xu, Zhaowu; Li, Yang; Ma, Xuemei; Gao, Xindong; Tian, He [Tetrahedron, 2008, vol. 64, # 8, p. 1860 - 1867]
[5]Location in patent: scheme or table Ke, Shao-Yong; Qian, Xu-Hong; Liu, Feng-Yi; Wang, Ni; Yang, Qing; Li, Zhong [European Journal of Medicinal Chemistry, 2009, vol. 44, # 5, p. 2113 - 2121]
[6]Location in patent: scheme or table Rai, Ganesha; Kenyon, Victor; Jadhav, Ajit; Schultz, Lena; Armstrong, Michelle; Jameson, J. Brian; Hoobler, Eric; Leister, William; Simeonov, Anton; Holman, Theodore R.; Maloney, David J. [Journal of Medicinal Chemistry, 2010, vol. 53, # 20, p. 7392 - 7404]
[7]Location in patent: scheme or table Ghani, Usman; Ullah, Nisar [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 4042 - 4048] Location in patent: scheme or table Ke, Shaoyong; Liu, Fengyi; Wang, Ni; Yang, Qing; Qian, Xuhong [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 332 - 335]
[8]Location in patent: experimental part Carvalho, Samir A.; Feitosa, Larisse O.; Soares, Marcio; Costa, Thadeu E.M.M.; Henriques, Maria G.; Salomao, Kelly; De Castro, Solange L.; Kaiser, Marcel; Brun, Reto; Wardell, James L.; Wardell, Solange M.S.V.; Trossini, Gustavo H.G.; Andricopulo, Adriano D.; Da Silva, Edson F.; Fraga, Carlos A.M. [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 512 - 521]
[9]Du, Qian-Ru; Li, Dong-Dong; Pi, Ya-Zhou; Li, Jing-Ran; Sun, Jian; Fang, Fei; Zhong, Wei-Qing; Gong, Hai-Bin; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297]
[10]Harikishore, Amaravadhi; Leow, Min Li; Niang, Makhtar; Rajan, Sreekanth; Pasunooti, Kalyan Kumar; Preiser, Peter Rainer; Liu, Xuewei; Yoon, Ho Sup [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 11, p. 1097 - 1101]
[11]Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985]
[12]Khan, Mehebub Ali; Ghosh, Soumen; Bera, Sachinath; Hoque, Anamika; Sk, Ismail; Ansari, Shagufi Naz; Mobin, Shaikh M.; Alam, Md. Akhtarul [Journal of Organic Chemistry, 2020, vol. 85, # 6, p. 4019 - 4025]
[13]Baud, Damien; Bebrone, Carine; Becker, Katja; Benvenuti, Manuela; Cerboni, Giulia; Chelini, Giulia; Cutolo, Giuliano; De Luca, Filomena; Docquier, Jean-Denis; Feller, Georges; Fischer, Marina; Galleni, Moreno; Gavara, Laurent; Gresh, Nohad; Kwapien, Karolina; Legru, Alice; Mangani, Stefano; Mercuri, Paola; Pozzi, Cecilia; Sannio, Filomena; Sevaille, Laurent; Tanfoni, Silvia; Verdirosa, Federica; Berthomieu, Dorothée; Bestgen, Benoît; Frère, Jean-Marie; Hernandez, Jean-François [European Journal of Medicinal Chemistry, 2020, vol. 208]
[14]Gavara, Laurent; Legru, Alice; Verdirosa, Federica; Sevaille, Laurent; Nauton, Lionel; Corsica, Giuseppina; Mercuri, Paola Sandra; Sannio, Filomena; Feller, Georges; Coulon, Rémi; De Luca, Filomena; Cerboni, Giulia; Tanfoni, Silvia; Chelini, Giulia; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [Bioorganic Chemistry, 2021, vol. 113]
  • 9
  • [ 19213-72-0 ]
  • [ 93-09-4 ]
  • [ 3007-91-8 ]
Reference： [1]Organic Letters,2012,vol. 14,p. 1970 - 1973
  • 10
  • [ 3007-91-8 ]
  • [ 33950-71-9 ]
  • [ 7163-25-9 ]
Reference： [1]Organic Letters,2012,vol. 14,p. 2874 - 2877
  • 11
  • [ 2243-82-5 ]
  • [ 64-17-5 ]
  • [ 3007-91-8 ]
YieldReaction ConditionsOperation in experiment
92% With potassium hydrogensulfate; at 78℃; for 48h; General procedure: A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the product). Removal of hexanes in vacuo provided the following pure products
Reference： [1]Arkivoc,2018,vol. 2018,p. 174 - 183
[2]RSC Advances,2018,vol. 8,p. 4571 - 4576
  • 12
  • [ 3007-91-8 ]
  • [ 17955-46-3 ]
  • [ 972-11-2 ]
Reference： [1]Organic Letters,2018,vol. 20,p. 385 - 388
  • 13
  • [ 447-53-0 ]
  • [ 4755-77-5 ]
  • [ 3007-91-8 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 1,2-Dihydronaphthalene; Ethyl oxalyl chloride With 2,6-dimethylpyridine; tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 60℃; for 84h; Inert atmosphere; Irradiation; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.5h; 13 Example 13 At room temperature, add 0.2mmol of 1,2-dihydronaphthalene, 0.3mmol of ethyl chlorooxalate, 0.3mmol of 2,6-lutidine, and 0.004mmol of photocatalyst Ru(bpy)3Cl2 to a dry test tube. , plug the reaction tube with a stopper and put it under nitrogen protection, then add 4.0 mL of acetonitrile, stir for 84 hours under 60 degrees Celsius light conditions, and then drop to room temperature and add 1.0 mmol of DBU to react for 0.5 hours. After the complete reaction was monitored by TLC, the reaction solution was poured into ethyl acetate for extraction (20 mL×3), the organic phases were combined and washed twice with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure, using petroleum ether and acetic acid The mixture of ethyl esters is used as the mobile phase for column chromatography separation, and the corresponding ethyl 3,4-dihydronaphthalene-2-carboxylate can be obtained with a yield of 52% (Example 13).
Reference： [1]Current Patent Assignee: TAIZHOU UNIVERSITY - CN113233980, 2021, A Location in patent: Paragraph 0108-0112

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