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[ CAS No. 112-05-0 ] {[proInfo.proName]}

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Chemical Structure| 112-05-0
Chemical Structure| 112-05-0
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Product Details of [ 112-05-0 ]

CAS No. :112-05-0 MDL No. :MFCD00004433
Formula : C9H18O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FBUKVWPVBMHYJY-UHFFFAOYSA-N
M.W :158.24 Pubchem ID :8158
Synonyms :
Nonanoic acid

Calculated chemistry of [ 112-05-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 7
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.15
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 3.42
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 2.2
Consensus Log Po/w : 2.6

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.485 mg/ml ; 0.00306 mol/l
Class : Soluble
Log S (Ali) : -3.88
Solubility : 0.0207 mg/ml ; 0.000131 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.46
Solubility : 0.546 mg/ml ; 0.00345 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 112-05-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 112-05-0 ]

* 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.

  • Upstream synthesis route of [ 112-05-0 ]
  • Downstream synthetic route of [ 112-05-0 ]

[ 112-05-0 ] Synthesis Path-Upstream   1~25

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Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 19, p. 6727 - 6733
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Reference: [1] Environmental Science and Technology, 1998, vol. 32, # 16, p. 2357 - 2370
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  • [ 123-29-5 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 7 - 11
[2] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 5, p. 905 - 908
[3] Bulletin des Societes Chimiques Belges, 1931, vol. 40, p. 390
[4] Justus Liebigs Annalen der Chemie, 1872, vol. 164, p. 337
[5] Yakugaku Zasshi, 1927, p. 150[6] Chem. Zentralbl., 1928, vol. 99, # I, p. 1643
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Reference: [1] Chinese Journal of Chemistry, 2011, vol. 29, # 10, p. 2153 - 2156
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Reference: [1] Helvetica Chimica Acta, 1944, vol. 27, p. 957
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Reference: [1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5>14, p. I,467[2] Gazzetta Chimica Italiana, 1906, vol. 36 I, p. 108
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Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 9, p. 3382 - 3390
[2] Journal of the American Chemical Society, 1989, vol. 111, # 9, p. 3382 - 3390
[3] Journal of Organic Chemistry, 1987, vol. 52, # 16, p. 3698 - 3699
[4] Journal of Organic Chemistry, 1987, vol. 52, # 16, p. 3698 - 3699
[5] Journal of the American Chemical Society, 2002, vol. 124, # 15, p. 3824 - 3825
[6] Green Chemistry, 2010, vol. 12, # 10, p. 1726 - 1733
[7] Patent: WO2011/80297, 2011, A1, . Location in patent: Page/Page column 9-10
[8] Patent: US2012/245375, 2012, A1, . Location in patent: Page/Page column 4
[9] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[10] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[11] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[12] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[13] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[14] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[15] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[16] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[17] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[18] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[19] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[20] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[21] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[22] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[23] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[24] Green Chemistry, 2017, vol. 19, # 12, p. 2855 - 2862
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Reference: [1] Patent: US2012/245375, 2012, A1, . Location in patent: Page/Page column 4-5
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Reference: [1] Patent: WO2011/80297, 2011, A1, . Location in patent: Page/Page column 11-12
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Reference: [1] Patent: US2012/302778, 2012, A1, . Location in patent: Page/Page column 4
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Reference: [1] Patent: WO2007/39481, 2007, A1, . Location in patent: Page/Page column 6
[2] Patent: WO2007/39481, 2007, A1, . Location in patent: Page/Page column 7
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[2] ChemSusChem, 2018, vol. 11, # 19, p. 3431 - 3437
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[2] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[2] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[2] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[3] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[2] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[3] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[4] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[5] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[6] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
[7] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
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Reference: [1] Green Chemistry, 2010, vol. 12, # 10, p. 1726 - 1733
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
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Reference: [1] Physical Chemistry Chemical Physics, 2014, vol. 16, # 26, p. 13220 - 13228
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Reference: [1] ChemSusChem, 2018, vol. 11, # 19, p. 3431 - 3437
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Reference: [1] RSC Advances, 2013, vol. 3, # 1, p. 172 - 180
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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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YieldReaction ConditionsOperation in experiment
81.1% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Into a reactor equipped with a heating, stirring, and a thermometer, 112 g of vanillin amine hydrochloride obtained above was added to 670 ml of a DMF solvent, and the mixture was stirred at room temperature until the solid was completely dissolved and 95.2 g Nonanoic acid was added thereto.The was cooled to 0°C with an ice bath, 134.4g of triethylamine was added, the temperature was stabilized at 0-5°C, and 235.2g of a condensing agent HBTU was added under stirring. The reaction was naturally warmed to room temperature and stirred overnight. After the reaction was completely detected by TLC, Add 1100 ml of ethyl acetate and 330 ml of water to the reaction mixture. Stir well and place in liquid in a separatory funnel. Discard the aqueous layer and obtain ethyl acetate layers of 5 wtpercent sodium bicarbonate solution, 2 wtpercent hydrochloric acid, respectively. The saturated brine was washed three times each, 1200 ml/time, and then 100 g of anhydrous sodium sulfate was added to the ethyl acetate layer for drying for 3 hours. The sodium sulfate was removed by filtration, and the filtrate was placed in a reactor and heated to 45° C. with stirring and reduced. About 820 ml of ethyl acetate was distilled off and cooled to room temperature. 540 ml of petroleum ether was added to crystallize for 3 hours and filtered. The solid was dried at 40-45° C. for 10 hours to obtain 156.4 g of Nonivamide as the target product. The total yield was 81.1percent. The obtained capsaicin was analyzed by HPLC and its purity was 98.8percent.
Reference: [1] Patent: CN103288665, 2017, B, . Location in patent: Paragraph 0029; 0031; 0032; 0034
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2595 - 2604
[2] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 2113 - 2118
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