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[ CAS No. 99199-60-7 ] {[proInfo.proName]}

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Chemical Structure| 99199-60-7
Chemical Structure| 99199-60-7
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Product Details of [ 99199-60-7 ]

CAS No. :99199-60-7 MDL No. :MFCD07778357
Formula : C10H9FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZNJANLXCXMVFFI-UHFFFAOYSA-N
M.W : 196.18 Pubchem ID :15382843
Synonyms :

Calculated chemistry of [ 99199-60-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.13
TPSA : 46.53 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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 1.7
Log Po/w (SILICOS-IT) : 2.07
Consensus Log Po/w : 1.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.641 mg/ml ; 0.00327 mol/l
Class : Soluble
Log S (Ali) : -2.47
Solubility : 0.667 mg/ml ; 0.0034 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.792 mg/ml ; 0.00404 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 99199-60-7 ]

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 [ 99199-60-7 ]

* 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 [ 99199-60-7 ]
  • Downstream synthetic route of [ 99199-60-7 ]

[ 99199-60-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 99199-59-4 ]
  • [ 99199-60-7 ]
YieldReaction ConditionsOperation in experiment
88.4% at 70 - 80℃; for 0.5 h; Inert atmosphere; Sealed tube 30 g (0.144 mol)6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid,5gWet palladium on carbon (5percent Pd on carbon, 50percent water content)500 mL of glacial acetic acid,Placed with high pressure hydrogenIn the kettle,Sealed nitrogen protection three times,After replacing the nitrogen with hydrogen,Pressurized hydrogen to 2. OMPa,Heating reactor to 70 ~ 80 ° C,When the hydrogen pressure in the kettle drops,Timely add hydrogen to 2. OMPa,When the reactor pressure within half an hour does not change,Always maintain 2. OMPa,Which is regarded as the end of the reaction,After the hydrogen was removed from the autoclave,The reaction solution was filtered to recover Pd / C,The filtrate was concentrated under reduced pressure to recover glacial acetic acid,The remaining concentrate was poured into 30 ml of petroleum ether while hot,A white crystalline solid,The solid was filtered,Dried to give 25 g of white 6-fluorochroman-2-carboxylic acid as a solid,The yield was 88.4percentThe purity was 99.8percent.
83% With acetic acid In petroleumether a)
A mixture of 63.4 parts of 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid and 400 parts of acetic acid was hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10percent.
After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated.
The residue was stirred in petroleumether.
The product was filtered off and dried in vacuo at 70° C., yielding 49 parts (83percent) of 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (int. 1).
83.3% With acetic acid In Petroleum ether EXAMPLE 2
A mixture of 63.4 parts of 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid and 400 parts of acetic acid was hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10percent.
After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated.
The residue was stirred in petroleum ether.
The product was filtered off and dried in vacuo at about 70° C., yielding 49 parts (83.3percent) of 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (intermediate 5).
Reference: [1] Patent: CN104072470, 2016, B, . Location in patent: Paragraph 0060; 0061
[2] Journal of Chemical Research, 2006, # 12, p. 807 - 808
[3] Patent: US6545040, 2003, B1,
[4] Patent: US4654362, 1987, A,
[5] Patent: US2004/82592, 2004, A1,
[6] Patent: WO2006/25070, 2006, A2, . Location in patent: Page/Page column 12-13
  • 2
  • [ 874649-82-8 ]
  • [ 99199-60-7 ]
Reference: [1] Tetrahedron Asymmetry, 2015, vol. 26, # 17, p. 912 - 917
  • 3
  • [ 371-41-5 ]
  • [ 99199-60-7 ]
Reference: [1] Patent: CN104072470, 2016, B,
[2] Patent: CN104072470, 2016, B,
[3] Patent: CN108148032, 2018, A,
  • 4
  • [ 134102-10-6 ]
  • [ 99199-60-7 ]
Reference: [1] Tetrahedron Asymmetry, 2015, vol. 26, # 17, p. 912 - 917
  • 5
  • [ 99199-60-7 ]
  • [ 67-56-1 ]
  • [ 874649-82-8 ]
YieldReaction ConditionsOperation in experiment
98% at 25 - 30℃; Exampe1: Synthesis of methyl of Form u a3:A sokition of add (100gm: 0.510 moles) in methanol (500mi) is prepared in Ilk Round Bottom Flask (RBF) at Room Temperature (RT, 2530°C). 19.9 gm of sulphuric add is added and strred reaction mass at RT (2530°C) for 35 hrs. Methanol is distifled out under vacuum at 4045°C. in the reaction mixture is added 500 ml MDC and 500 ml purified water, Organic layer is washed with 500 ml purifiedwater and 500 ml sodium bicarbonate solution. Organic layer finally washed with 500 ml purified water. Organic layer dried over 20gm sodium sulphate. MDC is distilled under high vacuum and degas at 50°C to obtained oily mass of methyl 64luor&-3,4dihydro2Hchromene 2carboxylate of Formula3. Weight of oil102 gm HPLC purity 99.97percent; Yield 98percent.
97% at 30℃; Reflux 100 gm of 6-fluoro-3,4-dihydro-2H-l-benzopyran-2-carboxylic acid was charged in 500 ml of methanol under stirring and then added 2 gms of concentrated sulfuric acid at around 30°C. Then, reaction mixture was slowly heated to reflux temperature. Reaction was maintained at the reflux temperature. After reaction, methanol was distilled and product was extracted with toluene. Toluene solution was washed with 5percent sodium bicarbonate solution. Toluene layer was concentrated to get 104 gm of Methyl 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylate. 97percent. Purity (GC areapercent)= 99.5percent
87.9%
Stage #1: at 20 - 60℃; for 3.5 h;
Stage #2: With water; sodium hydrogencarbonate In methanol
Example 1Synthesis of methyl 6-fluoro-3,4-dihvdro-2H-chromen-2-carboxylate. Acid 6-fluoro-3,4-dihydro-2H-chromen-2-carboxylic (10.0 g, 51.0 mmol, 96.8 Apercent) was dissolved in MeOH (50 ml) under nitrogen at 20°C. To the stirred solution was added H2SO4 (0.51 g, 5.0 mmol, 96.0percent) and the mixture heated to 60°C in 15 min. <n="11"/>After 3 hours under stirring at 600C, the reaction was cooled to 25°C in 15 min. and concentrated under vacuum to half volume (25 ml). A 5percent aqueous solution of NaHCO3 (50 ml) was added to the residue, followed by ethyl acetate (100 ml). The strata were separated and the organic phase dried on Na2SO4, filtered and concentrated at reduced pressure to give methyl 6-fluoro-3,4-dihydro-2H-chromen-2- carboxylate as a pale yellow oil (9.41 g, 87.9percent yield, 96.8 Apercent). δH(400 MHz; CDCl3) 6.89-6.79 (2H, m, Ar), 6.77-6.76-6.72 (IH, m, Ar), 4.73-4.69 (IH, m), 3.79 (3H, s), 2.87-2.69 (2H, m), 2.31-2.12 (2H, m).
Reference: [1] Patent: WO2014/111903, 2014, A2, . Location in patent: Page/Page column 6
[2] Patent: WO2016/185492, 2016, A1, . Location in patent: Page/Page column 13
[3] Patent: WO2008/40528, 2008, A2, . Location in patent: Page/Page column 9-10
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