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[ CAS No. 1196-92-5 ]

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2D
Chemical Structure| 1196-92-5
Chemical Structure| 1196-92-5
Structure of 1196-92-5 *Storage: {[proInfo.prStorage]}

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Product Details of [ 1196-92-5 ]

CAS No. :1196-92-5MDL No. :MFCD00044577
Formula : C8H11NO2 Boiling Point : 292.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :153.18Pubchem ID :-
Synonyms :

Computed Properties of [ 1196-92-5 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 1196-92-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1196-92-5 ]

  • Upstream synthesis route of [ 1196-92-5 ]
  • Downstream synthetic route of [ 1196-92-5 ]

[ 1196-92-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 764-85-2 ]
  • [ 1196-92-5 ]
  • [ 2444-46-4 ]
YieldReaction ConditionsOperation in experiment
88.6% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; To a solution of the hydrochloride or hydrobromide salt of an amine (1 mmol) in anhydrous N,N- dimethylformamide (DMF) (2 mL) was added N, N- diisopropylethylamine (DIPEA) (2 mmol) to liberate the amine. After stirring at room temperature for 10 min, nonanoyl chloride (1 mmol) was added. The solution was stirred at room temperature for 6 to 24 h. After the reaction, water (40 mL) was added to the solution. The reaction mixture was transferred to a separating funnel and extracted with dichloromethane, CH2Cl2 (3 * 6 mL) . The organic extracts were concentrated under reduced pressure to give a crude product. The crude product was then purified by silica gel column chromatography (using hexane/ethyl acetate, 2:1 v/v, as eluent) or preparative HPLC (using the protocol set out in "Analytical Protocols" above) to give the final product.
Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 2113 - 2118
[2] Patent: WO2010/144055, 2010, A1, . Location in patent: Page/Page column 45-46; 50
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2595 - 2604
[4] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 855
[5] Journal of the American Chemical Society, 1919, vol. 41, p. 2121[6] Journal of the American Chemical Society, 1920, vol. 42, p. 597
[7] Journal of Medicinal Chemistry, 1993, vol. 36, # 16, p. 2362 - 2372
  • 2
  • [ 1196-92-5 ]
  • [ 112-05-0 ]
  • [ 2444-46-4 ]
YieldReaction ConditionsOperation in experiment
87.4% With boric acid In toluene at 130℃; for 8 h; In a three-neck 500 mL flask, 30.0 g (0.196 mol) of vanillin was added.31.0 g (0.196 mol) of n-decanoic acid and 300 mL of toluene were added.Boric acid 0.6g (9.8mmol), a three-neck flask fitted with a thermometer,A mouth water separator + reflux condenser (the water separator is loaded into the reaction flask,Then install the reflux condenser above the water separator.)Another mouth is closed, stirring is started, and the temperature is raised to 130°C for 8 hours.After the reaction is completed, it is cooled to room temperature.Add 50mL of water twice to wash (extract boric acid),After drying over anhydrous sodium sulfate,Recovery of toluene under reduced pressure at 60 °C using a rotary evaporatorTo the distillation of toluene is 2/3 of the original volume, stop decompression recovery,The remaining liquid is transferred to the cryogenic reactor,Stir and crystallize at -20°C for 3h, filter,The resulting crystals are washed with toluene.Drained to give 50.3 g of a white powdery solid with a yield of 87.4percent.HPLC purity 99.1percent.White powder solids analysis:
74% With Candida antarctica lipase B In toluene at 80℃; for 36 h; Inert atmosphere; Molecular sieve; Enzymatic reaction A microwave-vial containing a solution of 1 (0.2 mmol, 1.0 equiv.), ammonium formiate (37.8 mg, 0.6 mmol, 3.0 equiv.) and Pd°-catalyst(Pd°-AmP-MFC, 13.4 mg, 0.01 mmol, 8 wtpercent, 5 molpercent) or(Pd°-CPG, 569A, 74.0 mg, 0.013 mmol, 6.6 molpercent) in toluene (1 mL) under ISfc conditions was stirred at 80°C for the time shown in Table 3. Afterwards, molecular sieves 4A, acid 4 (0.2 mmol, 1.0 equiv.) and lipase (120 mg/mmol) were added to reaction mixture and stirred at 80°C for 36h. The crude reaction mixture was filtrated through Celite using CHCb(10 mL) as eluent and evaporated. The crude material was purified by silica gel flash column chromatography to afford the corresponding amide 3 as indicated in Table 3. The lipase is preferably Novozyme-435 immobilized on a macroporous anionic resin.
52% With lipase In tert-Amyl alcohol at 45℃; for 48 h; Molecular sieve; Enzymatic reaction The dried crude reaction mixture from the previous step (containing vanillylamine 94 mg, 0.62 mmol, 1.00 equiv.) was dissolved in 2-methyl-2-butanol (31 mL, 20 mM). To the reaction was added Ms 4A (2 g), compound 5b (98.7 mg, 0.62 mmol, 1.00 equiv.) and lipase (1.9 g, 20 mg/niL). The reaction was stirred at 45°C for 48 h. Afterwards the reaction was cooled to room temperature and filtered. The solvent was removed under reduced pressure and the crude material was purified by chromatography to afford nonivamide (7b) (isolated yield 52 percent) as light yellow oil.
Reference: [1] Patent: CN107793325, 2018, A, . Location in patent: Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033-0040
[2] Patent: WO2016/96905, 2016, A1, . Location in patent: Page/Page column 19
[3] ACS Catalysis, 2016, vol. 6, # 6, p. 3932 - 3940
[4] Patent: WO2015/144902, 2015, A1, . Location in patent: Page/Page column 11
[5] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 2113 - 2118
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  • [ 1196-92-5 ]
  • [ 1120-07-6 ]
  • [ 2444-46-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 16, p. 5227 - 5231
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  • [ 1196-92-5 ]
  • [ 31467-61-5 ]
  • [ 25775-90-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2595 - 2604
[2] Journal of Organic Chemistry, 1988, vol. 53, # 5, p. 1064 - 1071
[3] Journal of Organic Chemistry, 1989, vol. 54, p. 3477 - 3478
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