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[ CAS No. 20620-59-1 ] {[proInfo.proName]}

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Chemical Structure| 20620-59-1
Chemical Structure| 20620-59-1
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Product Details of [ 20620-59-1 ]

CAS No. :20620-59-1 MDL No. :MFCD00025896
Formula : C12H16O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BNNWLDUOVGYRLY-UHFFFAOYSA-N
M.W : 192.25 Pubchem ID :262942
Synonyms :

Safety of [ 20620-59-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20620-59-1 ]

* 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 [ 20620-59-1 ]

[ 20620-59-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 2270-20-4 ]
  • [ 20620-59-1 ]
YieldReaction ConditionsOperation in experiment
98% With sulfuric acid Reflux;
97% With 1,3,5-trichloro-2,4,6-triazine; sodium carbonate at 50℃; for 0.166667h; Sonication; General Procedure General procedure: The carboxylic acid (0.271 mmol), TCT (0.050 g, 0.271 mmol), PS-Ph3P (0.009 g, 0.027 mmol, loading 3.0 mmol/g), and Na2CO3 (0.057 g, 0.542 mmol) were added to MeOH (0.5 mL). Then the mixture was sonicated in an ultrasonic bath (Elmasonic S 30H) at 50°C for the specified time. After completion, the crude mixture was filtered through a short pad of silica to obtain the product after solvent evaporation. Whenever necessary, the product was further purified by flash chromatography.
96% With thionyl chloride at 0 - 20℃; for 2h;
93% With hydrogenchloride at 20℃;
93% With sulfuric acid
93% With sulfuric acid at 20℃;
92% With sulfuric acid for 16h;
51% With sulfuric acid Heating;
With boron trifluoride
With hydrogenchloride at 20℃; for 0.333333h; 27 5-Phenylpentanoic acid (10.0 g) was dissolved in 250 mL of methanol and sparged with hydrogen chloride gas at room temperature for 15 minutes. The solvent was then removed under vacuum. Methyl 5-phenylpentanoate obtained was used in the next step without further purification.
With sulfuric acid at 20℃; for 3h; 34.a a) Methyl 5-phenylpentanoateH2SO4 (1.7 ml_, 31.89 mmol) was added to a solution of 5-phenylpentanoic acid (15.0 g, 84.161 mmol) in MeOH (80 ml_). The reaction mixture was stirred at r.t. for 3 h, poured into H2O (400 ml_) and extracted with CH2CI2 (2x300 ml_). The organic layer was washed with NaHCO3 (300 ml_, saturated aqueous solution), dried over Na2SO4 (anhydrous), filtered and concentrated, to furnish methyl 5-phenylpentanoate (16.30 g, colourless oil, yield: 100%). The crude residue was submitted to next step without further purification. 1H NMR (CDCI3, 250 MHz) δ ppm: 7.45 (m, 2H), 7.35 (m, 3H), 3.84 (s, 3H), 2.81 (t, J = 7.2 Hz, 2H), 2.52 (t, J = 7.2 Hz, 2H), 1.84 (m, 4H).
With hydrogenchloride
With sulfuric acid
1.77 g With sulfuric acid for 1h; Reflux; Intermediate 22. methyl 5-phenylpentanoate General procedure: Alcohol XVII (1.0 eq.) was dissolved in water (2 mL per mmcl XVII) and conc H2S04 (0.05 mL per mmol XVII), then KMnO4 (2.0 eq.) was added in small portions at 0 °C. After complete addition, the solution was stirred at 25 °C for 1 h, and then was turned basic by addition of solid NaOH. The manganese salts were removed by filtration and the filtrate was extracted with diethyl ether. The aequeous layer was acidified by addition of 2N HCI and the precipitate was filtered off and driedunder reduced pressure to give the crude carboxylic acid which was used in the following step without further purification. The acid was dissolved in MeOH (2.0 mL per mmcl of acid), and S drops of conc H2S04 were added. The reaction was stirred at reflux for 1 h. The solution was then neutralized with sat. aq. Na2CO3 solution, extracted with EtOAc, and the solvent was evaporated on silica. The compound XIX was purified by column chromatography using the Teledyne ISCOapparatus (cyclohexane:EtOAc). The title compound was obtained according to the General Procedure X (Step 1) starting from 5-phenylpentan-1-ol (3.28 g, 20.0 mmol). Colorless liquid (1.77 g, 46%). 1H NMR (400 MHz, CDCI3)6 1.65 - 1.74 (m, 4H), 2.36 (t, J = 7.1 Hz, 2H), 2.65 (t, J = 7.1 Hz, 2H), 3.69 (s, 3H), 7.18 - 7.23 (m,3H), 7.27 - 7.33 (m, 2H). MS (ESI) m/z: 193 [M-H].
With sulfuric acid at 20℃; for 3.08333h; Reflux;

Reference: [1]Shing, Ka-Pan; Liu, Yungen; Cao, Bei; Chang, Xiao-Yong; You, Tingjie; Che, Chi-Ming [Angewandte Chemie - International Edition, 2018, vol. 57, # 37, p. 11947 - 11951][Angew. Chem., 2018, vol. 130, p. 12123 - 12127,5]
[2]Jaita, Subin; Phakhodee, Wong; Pattarawarapan, Mookda [Synlett, 2015, vol. 26, # 14, p. 2006 - 2008]
[3]Bai, Jinhong; Liao, Chenzhong; Liu, Yanghan; Qin, Xiaochu; Chen, Jiaxuan; Qiu, Yatao; Qin, Dongguang; Li, Zheng; Tu, Zheng-Chao; Jiang, Sheng [Journal of Medicinal Chemistry, 2016, vol. 59, # 12, p. 5766 - 5779]
[4]Benati, Luisa; Leardini, Rino; Minozzi, Matteo; Nanni, Daniele; Spagnolo, Piero; Strazzari, Samantha; Zanardi, Giuseppe [Organic Letters, 2002, vol. 4, # 18, p. 3079 - 3081]
[5]Kainmueller, Eva K.; Bannwarth, Willi [Helvetica Chimica Acta, 2006, vol. 89, # 12, p. 3056 - 3070]
[6]Location in patent: experimental part Estevez, M.-Carmen; Galve, Roger; Sanchez-Baeza, Francisco; Marco, M.-Pilar [Chemistry - A European Journal, 2008, vol. 14, # 6, p. 1906 - 1917]
[7]Albrecht, Martin; Keilwerth, Martin; Meyer, Karsten; Pividori, Daniel M.; Stroek, Wowa [Journal of the American Chemical Society, 2021, vol. 143, # 48, p. 20157 - 20165]
[8]Din, Laily Bin; Meth-Cohn, Otto; Walshe, Nigel D. A. [Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 781 - 786]
[9]Khalaf,A.A.; Roberts,R.M. [Journal of Organic Chemistry, 1972, vol. 37, # 26, p. 4227 - 4235]
[10]Current Patent Assignee: ERRANT GENE THERAPEUTICS LLC - WO2006/52916, 2006, A2 Location in patent: Page/Page column 31
[11]Current Patent Assignee: ORYZON GENOMICS S.A. - WO2009/80722, 2009, A2 Location in patent: Page/Page column 56
[12]Kim, Boram; Lee, Junghoon; Seo, Jung Hwa; Wudl, Fred; Park, Sung Heum; Yang, Changduk [Journal of Materials Chemistry, 2012, vol. 22, # 43, p. 22958 - 22963]
[13]Kim, Sun Min; Kim, Dong Wan; Yang, Jung Woon [Organic Letters, 2014, vol. 16, # 11, p. 2876 - 2879]
[14]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; ISTITUTO ITALIANO DI TECNOLOGIA - WO2015/173169, 2015, A1 Location in patent: Page/Page column 22; 41; 47; 48
[15]Wei, Kaijie; Yang, Tonghao; Chen, Qing; Liang, Siyu; Yu, Wei [Chemical Communications, 2020, vol. 56, # 78, p. 11685 - 11688]
  • 2
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  • [ 41419-25-4 ]
  • 3
  • [ 34420-17-2 ]
  • [ 20620-59-1 ]
  • 4
  • [ 20620-59-1 ]
  • [ 1501-04-8 ]
YieldReaction ConditionsOperation in experiment
74% With 4,5,6,7-tetrafluoro-2-hydroxy-3-(2,2,2-trifluoroethoxy)-3-trifluoromethylisoindolin-1-one; oxygen; cobalt(II) acetate; manganese(III) triacetate dihydrate In 2,2,2-trifluoroethanol at 60℃; for 48h; chemoselective reaction; 3-Oxo-3-phenylpropyl 4-trifluoromethylbenzoate (37a) General procedure: To a solution of benzoate 36a (72.1 mg, 0.300 mmol) in 35(5.8 mg, 0.015 mmol), TFE (0.15 mL), Co(OAc)2 (0.53 mg,0.00300 mmol) and Mn(OAc)3·H2O (0.80 mg, 0.00300 mmol)were added. The reaction mixture was stirred for 48 h at 60°Cunder O2 atmosphere. The mixture was evaporated under reducedpressure, and the residue was purified with flash columnchromatography (SiO2, n-hexane-EtOAc=9 : 1) to afford ketone37a (59.8 mg, 75%).
35% With N,N-dimethylaminomethylferrocene; oxygen In 1,4-dioxane at 80℃; for 15h; Schlenk technique; regioselective reaction;
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