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[ CAS No. 17720-60-4 ] {[proInfo.proName]}

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Chemical Structure| 17720-60-4
Chemical Structure| 17720-60-4
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Product Details of [ 17720-60-4 ]

CAS No. :17720-60-4 MDL No. :MFCD00498162
Formula : C14H12O4 Boiling Point : -
Linear Structure Formula :- InChI Key :KLFCJXAPIFIIFR-UHFFFAOYSA-N
M.W : 244.24 Pubchem ID :640096
Synonyms :

Calculated chemistry of [ 17720-60-4 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 67.19
TPSA : 77.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.91
Log Po/w (XLOGP3) : 2.69
Log Po/w (WLOGP) : 2.23
Log Po/w (MLOGP) : 1.41
Log Po/w (SILICOS-IT) : 2.28
Consensus Log Po/w : 1.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.34
Solubility : 0.111 mg/ml ; 0.000453 mol/l
Class : Soluble
Log S (Ali) : -3.98
Solubility : 0.0258 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.069 mg/ml ; 0.000282 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 17720-60-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280 UN#:N/A
Hazard Statements:H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17720-60-4 ]

* 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 [ 17720-60-4 ]
  • Downstream synthetic route of [ 17720-60-4 ]

[ 17720-60-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 156-38-7 ]
  • [ 108-46-3 ]
  • [ 17720-60-4 ]
YieldReaction ConditionsOperation in experiment
87% With boron trifluoride diethyl etherate In toluene at 100 - 108℃; for 1.5 h; Inert atmosphere Step 1: Reaction to produce l-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)ethanone [00165] Resorcinol (1,3-dihydroxybenzene) (62.000 g, 563.1 mmol, 1.0 equiv.) and 4- Hydroxyphenylacetic acid (94.237 g, 619.4 mmol, 1.1 equiv.) were added to a 3 neck 2 L round bottomed flask fitted with a paddle, a pressure equalizing addition funnel and a thermometer and a heating mantle. Toluene (350 mL) was added to the flask to give a suspension. The reaction purged with nitrogen and the addition funnel filled with Boron trifluoride etherate (198.201 ml, 1578.0 mmol, 2.8 equiv.) via canula. The reaction was stirred at 150 rpm and boron trifluoride etherate was added in portions of 3-4 mL and the reaction heated. During addition the internal temperature rose to 100 °C. The reaction went through various changes in color from yellow to dark red. After complete addition of boron trifluoride etherate the addition funnel was removed and replaced with a condenser. The reaction was stirred for 1.5 h at an internal temperature of 108 °C. A sample was taken and HPLC analysis indicated the reaction was complete. The reaction was cooled and stirring stopped to give a biphasic solution. A 12 percent aqueous solution of sodium acetate (41 g, 336 mL) was slowly added to the reaction with stirring. The reaction was stirred for 16 hours. A precipitate formed overnight and was collected in a sintered glass funnel. The solid was dried on a vacuum oven for 16 h to give the product as a white powder (119.67 g, 87.0 percent).
87% With boron trifluoride diethyl etherate In toluene at 100 - 108℃; for 1.5 h; Inert atmosphere [00195] Resorcinol (1,3-dihydroxybenzene) (62.000 g, 563.1 mmol, 1.0 equiv.) and 4- Hydroxyphenylacetic acid (94.237 g, 619.4 mmol, 1.1 equiv.) were added to a 3 neck 2 L round bottomed flask fitted with a paddle, a pressure equalizing addition funnel and a thermometer and a heating mantle. Toluene (350 mL) was added to the flask to give a suspension. The reaction purged with nitrogen and the addition funnel filled with Boron trifluoride etherate (198.20 1 ml, 1578.0 mmol, 2.8 equiv.) via canula. The reaction was stirred at 150 rpm and boron trifluoride etherate was added in portions of 3-4 mL and the reaction heated. During addition the internal temperature rose to 100 °C. The reaction went through various changes in color from yellow to dark red. After complete addition of boron trifluoride etherate the addition funnel was removed and replaced with a condenser. The reaction was stirred for 1.5 h at an internal temperature of 108 °C. A sample was taken and HPLC analysis indicated the reaction was complete. The reaction was cooled and stirring stopped to give a biphasic solution. A 12 percent aqueous solution of sodium acetate (41 g, 336 mL) was slowly added to the reaction with stirring. The reaction was stirred for 16 hours. A precipitate formed overnight and was collected in a sintered glass funnel. The solid was dried on a vacuum oven for 16 h to give the product as a white powder (119.67 g,87.0 percent).
87% With boron trifluoride diethyl etherate In toluene at 100 - 108℃; Inert atmosphere Step 1
Reaction to produce l-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)ethanone_:Resorcinol (1,3-dihydroxybenzene) (62.000 g, 563.1 mmol, 1.0 equiv.) and 4- Hydroxyphenyl acetic acid (94.237 619.4 mmol, 1.1 equiv.) were added to a 3 neck 2 L round bottomed flask fitted with a paddle, a pressure equalizing addition funnel and a thermometer and a heating mantle. Toluene (350 mL) was added to the flask to give a suspension. The reaction purged with nitrogen and the addition funnel filled with Boron trifluoride etherate (198.201 ml, 1578.0 mmol, 2.8 equiv.) via canula. The reaction was stirred at 150 rpm and boron trifluoride etherate was added in portions of 3-4 mL and the reaction heated. During addition the internal temperature rose to 100 °C. The reaction went through various changes in color from yellow to dark red. After complete addition of boron trifluoride etherate the addition funnel was removed and replaced with a condenser. The reaction was stirred for 1.5 h at an internal temperature of 108 °C. A sample was taken and HPLC analysis indicated the reaction was complete. The reaction was cooled and stirring stopped to give a biphasic solution. A 12 percent aqueous solution of sodium acetate (41 g, 336 mL) was slowly added to the reaction with stirring. The reaction was stirred for 16 hours. A precipitate formed overnight and was collected in a sintered glass funnel. The solid was dried on a vacuum oven for 16 h to give the product as a white powder (119.67 g, 87.0 percent).
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 12, p. 3005 - 3008
[2] Journal of Organic Chemistry, 2000, vol. 65, # 8, p. 2305 - 2308
[3] Journal of Agricultural and Food Chemistry, 1994, vol. 42, # 9, p. 1869 - 1871
[4] Tetrahedron Letters, 2006, vol. 47, # 47, p. 8375 - 8378
[5] Patent: WO2013/90921, 2013, A1, . Location in patent: Paragraph 00165
[6] Patent: WO2014/203129, 2014, A1, . Location in patent: Paragraph 00195
[7] Patent: WO2014/203132, 2014, A1, . Location in patent: Paragraph 00105; 00106
[8] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 11, p. 3703 - 3710
[9] Patent: EP1167364, 2002, A1, . Location in patent: Page 13
[10] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 4, p. 346 - 360
[11] Tetrahedron Letters, 2012, vol. 53, # 49, p. 6697 - 6700,4
[12] Tetrahedron Letters, 2012, vol. 53, # 49, p. 6697 - 6700
[13] Journal of Medicinal Chemistry, 1997, vol. 40, # 14, p. 2117 - 2122
[14] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4360 - 4366
[15] Bulletin de la Societe Chimique de France, 1951, p. 82
[16] Patent: US6670346, 2003, B1, . Location in patent: Page column 31; 34
[17] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 677 - 681
[18] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 18, p. 10027 - 10032
[19] Chemical and Pharmaceutical Bulletin, 2012, vol. 60, # 4, p. 513 - 520
[20] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 17, p. 5523 - 5526
[21] Patent: US2015/250802, 2015, A1, . Location in patent: Paragraph 0228
[22] Patent: EP3178480, 2017, A1, . Location in patent: Paragraph 0142
  • 2
  • [ 156-38-7 ]
  • [ 108-46-3 ]
  • [ 17720-60-4 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 50 - 60℃;
Stage #2: With water In diethyl ether at 0 - 20℃;
EXAMPLE 62: Trihydroxybenzoin
Resorcinol (100 g, 0.91 mol) and 4-hydroxyphenylacetic acid (138.4 g, 0.91 mol) were dissolved into BF3Et2O (346 ml, 2.73 mol) under N2.
The mixture was stirred and heated at 50-60°C.
After complete reaction, the mixture was cooled to room temperature and poured into a large volume of iced water.
The crude product was filtered off and dried to yield trihydroxybenzoin (70 percent).
mp 211°C.
1H-NMR (Acetone d6): 4.12 (s, 2H), 6.78 (d, 2H), 6.91 (d, 1H), 7.13 (d, 2H), 7.54-7.6 (m, 2H), 8.21 (s, 1H), 8.35 (s, 1H), 8.70 (s, 1H).
Reference: [1] Patent: EP1647549, 2006, A1, . Location in patent: Page/Page column 23
  • 3
  • [ 14191-95-8 ]
  • [ 108-46-3 ]
  • [ 17720-60-4 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 39, p. 5460 - 5463
[2] Monatshefte fuer Chemie, 1938, vol. 71, p. 215,226
[3] Justus Liebigs Annalen der Chemie, 1931, vol. 489, p. 118,127, 140
  • 4
  • [ 156-38-7 ]
  • [ 108-46-3 ]
  • [ 17720-60-4 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 3, p. 469 - 484
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 2000, vol. 4, p. 567 - 570
  • 5
  • [ 67804-60-8 ]
  • [ 17720-60-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7917 - 7928
  • 6
  • [ 111797-19-4 ]
  • [ 17720-60-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1959, vol. 32, p. 11
  • 7
  • [ 108-46-3 ]
  • [ 17720-60-4 ]
Reference: [1] Chemical Biology and Drug Design, 2013, vol. 82, # 3, p. 317 - 325
  • 8
  • [ 140-53-4 ]
  • [ 17720-60-4 ]
Reference: [1] Chemical Biology and Drug Design, 2013, vol. 82, # 3, p. 317 - 325
  • 9
  • [ 104-92-7 ]
  • [ 17720-60-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7917 - 7928
  • 10
  • [ 829-20-9 ]
  • [ 17720-60-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7917 - 7928
  • 11
  • [ 487-49-0 ]
  • [ 17720-60-4 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 136 - 139
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