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[ CAS No. 4687-37-0 ] {[proInfo.proName]}

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Chemical Structure| 4687-37-0
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Product Details of [ 4687-37-0 ]

CAS No. :4687-37-0 MDL No. :MFCD03424826
Formula : C13H16O5 Boiling Point : -
Linear Structure Formula :H2C3O2(C6H5C2H4O2)OCH3CH2 InChI Key :BHSYONGONOKNAI-UHFFFAOYSA-N
M.W : 252.26 Pubchem ID :2758465
Synonyms :

Calculated chemistry of [ 4687-37-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.33
TPSA : 61.83 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) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 1.84
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.979 mg/ml ; 0.00388 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.346 mg/ml ; 0.00137 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.49
Solubility : 0.0811 mg/ml ; 0.000321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.1

Safety of [ 4687-37-0 ]

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 [ 4687-37-0 ]

* 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 [ 4687-37-0 ]
  • Downstream synthetic route of [ 4687-37-0 ]

[ 4687-37-0 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1131-62-0 ]
  • [ 105-58-8 ]
  • [ 4687-37-0 ]
YieldReaction ConditionsOperation in experiment
76% With sodium hydride In toluene; mineral oil General procedure: The substrate b-ketoesters 10 a–n were either purchased or synthesized following published procedures. Some benzoylacetates were commercially available. Ethyl 3-oxo-3-phenyl propanoate (10a) was purchased. The reaction of benzoylacetates 10 b–n was prepared as described in previous reports. 25–27 A solution of a substituted acetophenone 8 a–n (0.05 mol) dissolved in toluene (50 mL) was added dropwise to a solution containing diethyl carbonate (9) (0.10 mol) and sodium hydride (0.15 mol 60percent dispersion in mineral oil). The mixture was stirred at room temperature, and then refluxed for 30 min. The mixture was poured into ice water,acidified with glacial acetic acid, and extracted with EtOAc (3x100 mL). The EtOAc extract was then dried over anhydrous MgSO4. After removal of the solvent in vacuo, the crude products were purified by silica gel column chromatography eluting with dichloromethane to afford benzoylacetates 10 b–n. All synthetic compounds were in agreement with 1H NMR, 13C NMR, IR and mass spectroscopic data.
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5064 - 5075
[2] Heterocycles, 1979, vol. 13, p. 239 - 246
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3217 - 3227
[4] Patent: JP2005/82549, 2005, A, . Location in patent: Page/Page column 19-20
[5] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7304 - 7307
[6] Organic and Biomolecular Chemistry, 2015, vol. 13, # 11, p. 3243 - 3254
[7] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3656 - 3660
[8] Tetrahedron Letters, 2016, vol. 57, # 27-28, p. 3024 - 3028
  • 2
  • [ 2033-24-1 ]
  • [ 64-17-5 ]
  • [ 3535-37-3 ]
  • [ 4687-37-0 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With pyridine In dichloromethane at -5 - 0℃; for 0.5 h;
Stage #2: at -5 - 25℃; for 1.5 h;
[Reference Example 1]
Ethyl 3-(3,4-dimethoxyphenyl)-3-oxopropionate
To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (14.4 g 10 mmol) in dichloromethane (30 mL), pyridine (0.81 mL, 10 mmol) was added at 0°C or less, and this was stirred at -5°C for 0.5 hours.
Subsequently, 3,4-dimethoxybenzoylchloride (2.00 g 10 mmol) was added at 0°C or less, stirred at -5°C for 0.5 hours, 0°C for 0.5 hours, and 25°C for 0.5 hours, and then 1 M hydrochloric acid (30 mL) was added while cooling on ice.
This was then extracted with dichloromethane.
After drying over magnesium sulfate, dichloromethane was distilled off, this was redissolved in ethanol (30 mL), refluxed for 1.5 hours, stirred at room temperature for 10 hours.
It was then stirred at 60°C for 14 hours, ethanol was distilled off, and this was purified by silica gel column chromatography (elude: hexane: tetrahydrofuran = 3:1) which resulted in a colorless oily material (2.27 g, 90percent yield).
Reference: [1] Patent: EP1900728, 2008, A1, . Location in patent: Page/Page column 164-165
  • 3
  • [ 76787-81-0 ]
  • [ 4687-37-0 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 9, p. 748 - 749
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 10, p. 2477 - 2486
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 183 - 190
[4] Journal of the Indian Chemical Society, 1931, vol. 8, p. 271,273
[5] Journal of Chemical Research - Part S, 1998, # 3, p. 136 - 137
  • 4
  • [ 2859-78-1 ]
  • [ 6148-64-7 ]
  • [ 82102-37-2 ]
  • [ 4687-37-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 37, p. 9763 - 9766[2] Angew. Chem., 2013, vol. 125, # 37, p. 9945 - 9948
  • 5
  • [ 141-97-9 ]
  • [ 3535-37-3 ]
  • [ 4687-37-0 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2005, vol. 53, # 24, p. 9566 - 9570
[2] Pharmaceutical Chemistry Journal, 1988, vol. 22, # 1, p. 26 - 30[3] Khimiko-Farmatsevticheskii Zhurnal, 1988, vol. 22, # 1, p. 35 - 39
  • 6
  • [ 93-07-2 ]
  • [ 4687-37-0 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 10, p. 1665 - 1673
[2] Journal of Chemical Research - Part S, 1998, # 3, p. 136 - 137
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 10, p. 2477 - 2486
[4] Journal of the American Chemical Society, 1948, vol. 70, p. 60,62
  • 7
  • [ 6148-64-7 ]
  • [ 93-07-2 ]
  • [ 4687-37-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 3978 - 3984
  • 8
  • [ 851-36-5 ]
  • [ 4687-37-0 ]
  • [ 1131-62-0 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 10, p. 1665 - 1673
  • 9
  • [ 141-78-6 ]
  • [ 3535-37-3 ]
  • [ 4687-37-0 ]
Reference: [1] Tetrahedron Asymmetry, 1996, vol. 7, # 4, p. 1077 - 1088
[2] European Journal of Organic Chemistry, 2011, # 31, p. 6314 - 6319
  • 10
  • [ 623-73-4 ]
  • [ 120-14-9 ]
  • [ 4687-37-0 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 43, p. 13237 - 13252
  • 11
  • [ 3943-77-9 ]
  • [ 141-78-6 ]
  • [ 4687-37-0 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 60,62
[2] Farmaco, 2003, vol. 58, # 9, p. 795 - 808
  • 12
  • [ 3535-37-3 ]
  • [ 4687-37-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 10, p. 2477 - 2486
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 183 - 190
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 9, p. 748 - 749
  • 13
  • [ 4687-37-0 ]
  • [ 10535-17-8 ]
Reference: [1] Journal of Organic Chemistry, 1962, vol. 27, p. 2111 - 2114
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