Home Cart 0 Sign in  

[ CAS No. 6100-74-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 6100-74-9
Chemical Structure| 6100-74-9
Structure of 6100-74-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 6100-74-9 ]

Related Doc. of [ 6100-74-9 ]

Alternatived Products of [ 6100-74-9 ]

Product Details of [ 6100-74-9 ]

CAS No. :6100-74-9 MDL No. :MFCD00182975
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :YLTGFGDODHXMFB-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :95693
Synonyms :
Acetoisovanillone;Isoacetovanillone;Diosmin EP Impurity A;3'-Hydroxy-4'-methoxyacetophenone
Chemical Name :3'-Hydroxy-4'-methoxyacetophenone

Calculated chemistry of [ 6100-74-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.15
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.86
Solubility : 2.3 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (Ali) : -1.76
Solubility : 2.87 mg/ml ; 0.0173 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.28
Solubility : 0.876 mg/ml ; 0.00527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 6100-74-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6100-74-9 ]

* 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 [ 6100-74-9 ]
  • Downstream synthetic route of [ 6100-74-9 ]

[ 6100-74-9 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 88114-44-7 ]
  • [ 6100-74-9 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With aluminum (III) chloride In dichloromethane at 18℃; for 24 h;
Stage #2: With water In dichloromethane
3'-Hydroxy-4'-methoxyacetophenone (12); A solution of ketone 8 (250 mg, 1.20 mmol) in dry CH2Cl2 (3 mL) was treated with AlCl3(208 mg, 1.56 mmol) and the resulting mixture stirred at 18 °C under a nitrogen atmosphere for 24 h then partitioned between H2O (10 mL) and additional CH2Cl2 (10 mL). The separated aqueous phase was extracted with CH2Cl2 (1 x 10 mL) and the combined organic fractions then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing light-yellow oil was subjected to flash chromatography (1:4 v/v ethyl acetate/hexane) to afford the title compound 124 (172 mg, 86percent) as a white solid, m.p. 88.6-90.5 °C (lit.4 m.p. 92-93 0C), Rf 0.4 in 1 : 1 v/v ethyl acetate/hexane.1H NMR (300 MHz) δ 7.53-7.56 (complex m, 2H), 6.89 (d, J 7.5 Hz, IH), 5.73 (broad s, IH), 3.96 (s, 3H), 2.54 (s, 3H).
Reference: [1] Patent: WO2008/124878, 2008, A1, . Location in patent: Page/Page column 38
  • 2
  • [ 1197-09-7 ]
  • [ 74-88-4 ]
  • [ 6100-74-9 ]
Reference: [1] Synthetic Communications, 1988, vol. 18, # 12, p. 1379 - 1384
[2] Patent: EP1447405, 2004, A1, . Location in patent: Page 28-29
[3] Patent: EP1566379, 2005, A1, . Location in patent: Page/Page column 21
  • 3
  • [ 1131-62-0 ]
  • [ 6100-74-9 ]
YieldReaction ConditionsOperation in experiment
47% at 65℃; for 46 h; A solution of ketone 6b (12.5 g, 69.5 mmol) in concentrated H2SO4 (62.5 mL) wasstirred at 65 °C for 46 h. After cooling the reaction mixture to ambient temperature, it was poured onto ice (250 g) and stirred for 1 h.The precipitate was filtered off, washed with water and redissolved in 1M aqueous NaOH (16 mL, 160 mmol). The mixture wasextracted with DCM (65 mL). The aqueous layer was acidified with concentrated HCl (25 mL), stirred for 1.5 h and the precipitatewas filtered off to give 5.39 g (47percent) of the phenol as brown solid with mp 80–81 °C (lit. [11] reports 88–90 °C). 1H NMR data are inaccordance with those published in ref.[11].
46.2% at 62 - 64℃; for 48 h; Dimethoxyacetophenone derivative (I) (72.08 g; 0.4 mol) was dissolved in sulfuric acid (360 ml), and then the mixture was stirred at 62 - 64 °C for 48 h. The reaction mixture was cooled to room temperature, poured into ice water (prepared from 2 kg of ice and 1.6 kg of water) and kept in a refrigerator overnight. The product was collected by filtration, washed with water (5x100 ml) and dried in vacuum at 40 °C until constant weight to obtain the product (40.4 g; 60.2 percent; HPLC purity: 96.4 percent). The crude product was dissolved in warm ethanol (80 ml) and precipitated by addition of n-heptane (80 ml). The mixture was cooled to 0 - 10 °C, stirred at this temperature for 1 h, the product was collected, washed with n-heptane (40 ml) and dried in a vacuum at 40°C until constant weight to obtain the purified product (30.77 g; 46.2 percent; HPLC purity: 99.5 percent).
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2877 - 2880
[2] Phytochemistry (Elsevier), 1991, vol. 30, # 7, p. 2438 - 2439
[3] European Journal of Organic Chemistry, 2006, # 17, p. 4044 - 4054
[4] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 884 - 892
[5] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 3, p. 670 - 684
[6] Patent: WO2017/59040, 2017, A1, . Location in patent: Paragraph 0076
[7] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 971 - 977
[8] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 4, p. 980 - 988
[9] Patent: US2007/259868, 2007, A1, . Location in patent: Page/Page column 16
[10] Patent: US2008/103168, 2008, A1, . Location in patent: Page/Page column 19
  • 4
  • [ 1131-62-0 ]
  • [ 6100-74-9 ]
  • [ 498-02-2 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 3, p. 186 - 188
[2] Patent: WO2006/61666, 2006, A2, . Location in patent: Page/Page column 22-23
  • 5
  • [ 1197-09-7 ]
  • [ 74-88-4 ]
  • [ 6100-74-9 ]
  • [ 1131-62-0 ]
Reference: [1] Heterocycles, 1997, vol. 44, # 1, p. 139 - 142
[2] Heterocycles, 1997, vol. 44, # 1, p. 139 - 142
  • 6
  • [ 621-59-0 ]
  • [ 6100-74-9 ]
Reference: [1] Synthesis, 2006, # 20, p. 3389 - 3396
[2] Patent: WO2008/124878, 2008, A1,
  • 7
  • [ 613-70-7 ]
  • [ 108-24-7 ]
  • [ 6100-74-9 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 225
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 225
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 225
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 225
  • 8
  • [ 613-70-7 ]
  • [ 6100-74-9 ]
Reference: [1] Helvetica Chimica Acta, 1927, vol. 10, p. 389
[2] Bulletin de la Societe Chimique de France, 1977, p. 901 - 905
  • 9
  • [ 29866-05-5 ]
  • [ 6100-74-9 ]
Reference: [1] Synthesis, 2006, # 20, p. 3389 - 3396
  • 10
  • [ 34123-66-5 ]
  • [ 6100-74-9 ]
Reference: [1] Patent: WO2008/124878, 2008, A1,
  • 11
  • [ 113964-90-2 ]
  • [ 6100-74-9 ]
Reference: [1] Patent: WO2008/124878, 2008, A1,
  • 12
  • [ 91-16-7 ]
  • [ 75-36-5 ]
  • [ 6100-74-9 ]
  • [ 1131-62-0 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 9, p. 3056 - 3062
[2] Journal of the American Chemical Society, 1980, vol. 102, # 9, p. 3056 - 3062
  • 13
  • [ 60792-88-3 ]
  • [ 6100-74-9 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1896
[2] Bulletin de la Societe Chimique de France, 1977, p. 901 - 905
  • 14
  • [ 3162-29-6 ]
  • [ 124-41-4 ]
  • [ 6100-74-9 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1567 - 1573
[2] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1567 - 1573
  • 15
  • [ 55761-46-1 ]
  • [ 6100-74-9 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 1102,1105[2] Chem.Abstr., 1954, p. 12024
  • 16
  • [ 90-05-1 ]
  • [ 75-36-5 ]
  • [ 6100-74-9 ]
Reference: [1] Helvetica Chimica Acta, 1927, vol. 10, p. 389
  • 17
  • [ 90-05-1 ]
  • [ 6100-74-9 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1896
  • 18
  • [ 30287-15-1 ]
  • [ 6100-74-9 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 1102,1105[2] Chem.Abstr., 1954, p. 12024
  • 19
  • [ 64-19-7 ]
  • [ 90-05-1 ]
  • [ 6100-74-9 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 280,291
  • 20
  • [ 613-70-7 ]
  • [ 7664-39-3 ]
  • [ 6100-74-9 ]
  • [ 498-02-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1954, vol. 587, p. 1,15
  • 21
  • [ 64-19-7 ]
  • [ 90-05-1 ]
  • [ 10025-87-3 ]
  • [ 6100-74-9 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 280,291
  • 22
  • [ 6100-74-9 ]
  • [ 100-39-0 ]
  • [ 23428-77-5 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With potassium carbonate In acetone at 20℃; for 0.5 h;
Stage #2: for 16 h; Reflux
In 200 ml flask solanaceae of, 3-hydroxy -4 methoxyacetic aminoacetophenone of 4. 66g (28. 1mmol, 1. 0eq. ), Potassium carbonate 3. 89g (28. 1mmol, 1. 0eq. ), Containing 50 ml monohydroxyacetone, 30 minutes after stirring at room temperature, 3 a benzyl bromide. 5 ml (29. 4mmol, 1. 0eq. ) Addition, 16 back to the time. After cooling, condensing, purified water is added to 150 ml, extracted with chloroform (100 ml × 4), magnesium sulfate waterlessly org. layer by drying, filtering, concentrated, recrystallization (ethyl acetate 3 ml), suction filtration, vacuum drying, a first crystal is obtained. Concentrating somas, recrystallization (ethyl acetate 0. 5 ml), suction filtration, vacuum drying, a second crystal is obtained. The corallite crystal (compd. (IV1)), yielding: 6. 69g (26. 1mmol, 93percent)is obtained.
Reference: [1] Patent: JP2015/214531, 2015, A, . Location in patent: Paragraph 0188; 0189; 0190
[2] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 1, p. 125 - 134
[3] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 884 - 892
[4] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 3, p. 670 - 684
[5] Phytochemistry (Elsevier), 1991, vol. 30, # 7, p. 2438 - 2439
[6] Patent: EP1447405, 2004, A1, . Location in patent: Page 28-29
[7] Patent: EP1566379, 2005, A1, . Location in patent: Page/Page column 21
  • 23
  • [ 6100-74-9 ]
  • [ 100-44-7 ]
  • [ 23428-77-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 854
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 3, p. 186 - 188
  • 24
  • [ 74-96-4 ]
  • [ 6100-74-9 ]
  • [ 31526-71-3 ]
YieldReaction ConditionsOperation in experiment
90.4% With potassium carbonate In N,N-dimethyl-formamide at 30 - 35℃; for 5 h; Purified compound II (24.9 g; 0.15 mol) was dissolved in dimethylformamide (80 ml) at room temperature. Potassium carbonate (27.6 g; 0.20 mol) was added to the mixture, then ethyl bromide (18.0 g; 0.165 mol) was added at a temperature not higher than 35 °C while stirring and cooling. The mixture was stirred at 30 - 35 °C for 5 h, then cooled to below 10 °C, diluted with water (240 ml) and stirred at 0 - 10 °C for 2 h. The product was collected, washed with water (2x100 ml) and dried in vacuum at 40 °C until constant weight to obtain the product (26.32 g; 90.4 percent; HPLC purity: 99.8 A percent).
86.5% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 4 h; The compound of formula 1 0 · 25mol, DMF 400mL, 0 · 25mol potassium carbonate and 1-bromoethane was added 0 · 30mol 1L 4-neck flask, 25 ° C reaction 4h. The reaction mixture was poured into 600mL water, stirred, and extracted with EA (100 ml x 3), the combined organic phase was washed with saturated brine (100mLXl), dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to give a white solid. Slurried with 100mL hexane 10min, filtered, the filter cake was dried in vacuo at 40 ° C for 5h, to give a white solid, 42g a yield of 86.5percent.
Reference: [1] Patent: WO2017/59040, 2017, A1, . Location in patent: Paragraph 0078
[2] European Journal of Organic Chemistry, 2006, # 17, p. 4044 - 4054
[3] Organic Letters, 2017, vol. 19, # 11, p. 2877 - 2880
[4] Patent: CN105622380, 2016, A, . Location in patent: Paragraph 0044; 0045; 0046; 0047
[5] Patent: US2007/259868, 2007, A1, . Location in patent: Page/Page column 16
[6] Patent: US2008/103168, 2008, A1, . Location in patent: Page/Page column 18-19
  • 25
  • [ 6100-74-9 ]
  • [ 75-03-6 ]
  • [ 31526-71-3 ]
YieldReaction ConditionsOperation in experiment
92.6% With potassium carbonate In N,N-dimethyl-formamide at 30 - 35℃; for 5 h; Purified compound II (29.9 g; 0.18 mol) was dissolved in dimethylformamide (90 ml) at room temperature. Potassium carbonate (34.8 g; 0.25 mol) was added to the mixture, and then ethyl iodide (31.2 g; 16.1 ml; 0.20 mol) was added at a temperature not higher than 35 °C while stirring and cooling. The mixture was stirred at 30 - 35 °C for 5 h, then cooled to below 10 °C, diluted with water (360 ml) and stirred at 0 - 10 °C for 2 h. The product was collected, washed with water (2x100 ml) and dried in a vacuum at 40 °C until constant weight to obtain the product (32.37 g; 92.6 percent; HPLC purity: 99.9 percent).
Reference: [1] Patent: WO2017/59040, 2017, A1, . Location in patent: Paragraph 0077
  • 26
  • [ 1117-96-0 ]
  • [ 6100-74-9 ]
  • [ 31526-71-3 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1567 - 1573
  • 27
  • [ 64-67-5 ]
  • [ 6100-74-9 ]
  • [ 31526-71-3 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 3, p. 186 - 188
  • 28
  • [ 6100-74-9 ]
  • [ 608141-43-1 ]
Reference: [1] Patent: CN105622380, 2016, A,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 6100-74-9 ]

Aryls

Chemical Structure| 1835-04-7

[ 1835-04-7 ]

1-(3,4-Dimethoxyphenyl)propan-1-one

Similarity: 0.98

Chemical Structure| 31526-71-3

[ 31526-71-3 ]

1-(3-Ethoxy-4-methoxyphenyl)ethanone

Similarity: 0.96

Chemical Structure| 586-37-8

[ 586-37-8 ]

3'-Methoxyacetophenone

Similarity: 0.95

Chemical Structure| 43113-94-6

[ 43113-94-6 ]

1-(3-Methoxy-5-methylphenyl)ethanone

Similarity: 0.95

Chemical Structure| 13575-75-2

[ 13575-75-2 ]

6,7-Dimethoxy-3,4-dihydronaphthalen-1(2H)-one

Similarity: 0.93

Ethers

Chemical Structure| 1835-04-7

[ 1835-04-7 ]

1-(3,4-Dimethoxyphenyl)propan-1-one

Similarity: 0.98

Chemical Structure| 31526-71-3

[ 31526-71-3 ]

1-(3-Ethoxy-4-methoxyphenyl)ethanone

Similarity: 0.96

Chemical Structure| 586-37-8

[ 586-37-8 ]

3'-Methoxyacetophenone

Similarity: 0.95

Chemical Structure| 43113-94-6

[ 43113-94-6 ]

1-(3-Methoxy-5-methylphenyl)ethanone

Similarity: 0.95

Chemical Structure| 13575-75-2

[ 13575-75-2 ]

6,7-Dimethoxy-3,4-dihydronaphthalen-1(2H)-one

Similarity: 0.93

Ketones

Chemical Structure| 1835-04-7

[ 1835-04-7 ]

1-(3,4-Dimethoxyphenyl)propan-1-one

Similarity: 0.98

Chemical Structure| 31526-71-3

[ 31526-71-3 ]

1-(3-Ethoxy-4-methoxyphenyl)ethanone

Similarity: 0.96

Chemical Structure| 2879-20-1

[ 2879-20-1 ]

1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone

Similarity: 0.96

Chemical Structure| 586-37-8

[ 586-37-8 ]

3'-Methoxyacetophenone

Similarity: 0.95

Chemical Structure| 43113-94-6

[ 43113-94-6 ]

1-(3-Methoxy-5-methylphenyl)ethanone

Similarity: 0.95