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[ CAS No. 101597-25-5 ] {[proInfo.proName]}

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Chemical Structure| 101597-25-5
Chemical Structure| 101597-25-5
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Product Details of [ 101597-25-5 ]

CAS No. :101597-25-5 MDL No. :MFCD00420323
Formula : C17H16O3 Boiling Point : -
Linear Structure Formula :HOC(CCH)(C6H4OCH3)2 InChI Key :RFNDMLXNYMQMGN-UHFFFAOYSA-N
M.W : 268.31 Pubchem ID :4644448
Synonyms :

Calculated chemistry of [ 101597-25-5 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.18
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 77.7
TPSA : 38.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.23
Log Po/w (XLOGP3) : 2.78
Log Po/w (WLOGP) : 2.54
Log Po/w (MLOGP) : 2.74
Log Po/w (SILICOS-IT) : 3.54
Consensus Log Po/w : 2.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.43
Solubility : 0.0986 mg/ml ; 0.000367 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.151 mg/ml ; 0.000564 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.73
Solubility : 0.00503 mg/ml ; 0.0000187 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.59

Safety of [ 101597-25-5 ]

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 [ 101597-25-5 ]

* 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 [ 101597-25-5 ]
  • Downstream synthetic route of [ 101597-25-5 ]

[ 101597-25-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 90-96-0 ]
  • [ 1066-54-2 ]
  • [ 101597-25-5 ]
YieldReaction ConditionsOperation in experiment
57.6%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 4 h; Inert atmosphere
Stage #2: With sodium hydroxide In methanol at 0℃;
General procedure: To a solution of (trimethylsilyl)acetylene (4.5 g, 45 mmol) in anhydrous THF (150 mL) under nitrogen atmosphere was added slowly n-BuLi (1.6 M in hexane, 28.5 mL, 45 mmol) at -10°C and the solution stirred 1h at - 10°C. A solution of benzophenone (7.44 g, 40.8 mmol) in dry THF (75 mL) was then added at -10°C. After 3h stirring at -10°C, the temperature was raised to 0°C and a solution of NaOH (2.16 g, 54 mmol) in MeOH (40,8 mL) was added. After the solution was warmed to room temperature, the solution was neutralized to pH 7 with acetic acid and the resulting solution poured into water (546 mL). The organic layer was extracted with EA (3x105 mL). The combined organic layers were dried over MgSO4. The crude product was recristallized from EA/PE to give 7,5 g of 1c as a light yellow solid (88,4percent).
Reference: [1] European Journal of Organic Chemistry, 2003, # 7, p. 1220 - 1230
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 17, p. 4341 - 4345[3] Angew.Chem.Int.Ed., 2014, vol. 53, p. 4341 - 4345,5
[4] Tetrahedron, 2011, vol. 67, # 2, p. 401 - 407
[5] European Journal of Organic Chemistry, 2011, # 11, p. 2111 - 2119
  • 2
  • [ 90-96-0 ]
  • [ 4301-14-8 ]
  • [ 101597-25-5 ]
YieldReaction ConditionsOperation in experiment
91% at 25 - 60℃; for 2 h; Inert atmosphere Ethynylmagnesium bromide (4 mmol, 0.5 M in THF) was added to the suspension of ketone 15 (0.5 g, 2.0 mmol) in THF (2 mL) at 25 °C.
The mixture was then stirred at 60 °C for 2 h and then quenched with saturated aqueous NH4Cl solution.
The aqueous layer was separated and extracted three times with Et2O.
The combined organic fractions were washed with brine, dried over Na2SO4 and concentrated under reduced pressure.
The crude product was recrystallized from Et2O/PE. White solid (490 mg, 91percent).
Mp: 90-91 °C. IR (KBr):  = 3472, 3245, 3004, 2959, 2932, 2836, 2545, 2102, 2039, 1933, 1902, 1886, 1870, 1683, 1635, 1607, 1584, 1506, 1464, 1455, 1440, 1415, 1350, 1305, 1295, 1251, 1241, 1199, 1180, 1164, 1199, 1180, 1164, 1119, 1062, 1025, 991, 967, 930, 897, 842, 882, 815, 782, 764, 732, 715, 685, 633, 627, 587, 526, 510, 488 cm-1. 1H NMR (500 MHz, CDCl3) δ 2.79 (s, 1H), 2.86 (s, 1H), 3.79 (s, 6H), 6.83-6.89 (m, 4H), 7.47-7.53 (m, 4H) ppm. 13C NMR (126 MHz, CDCl3) δ 55.42, 73.76, 75.22, 86.92, 113.68, 127.46, 137.06, 159.26 ppm. HRMS (EI): [M]+ calcd. for C17H16O3, 268.1099; found: 268.1096.
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 17, p. 4722 - 4726[2] Angew. Chem., 2018, vol. 130, p. 4812 - 4816,5
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3668 - 3687
[4] Molecules, 2012, vol. 17, # 5, p. 5177 - 5186
[5] Organic Letters, 2015, vol. 17, # 2, p. 242 - 245
  • 3
  • [ 90-96-0 ]
  • [ 101597-25-5 ]
YieldReaction ConditionsOperation in experiment
99 g With acetylene In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; mineral oil at 20℃; for 24 h; Inert atmosphere 18W percent sodium acetylide in xylene/mineral oil 121.1mL (0.45mol, 1eq) was dissolved in anhydrous THF (1L) saturated with acetylene gas. After that 4,4-dimethoxybenzophenone 100g (0.41mol, 1eq) was put inside the reaction mixture under nitrogen and stirred for 24h at room temperature. The product was extracted by solvent extraction using ethyl acetate and water, organic layer was dried with MgSO4 and solid product on vacuum drier. After complete drying, the product again dissolve in ethyl acetate and poured into 1L hexane slowly under stirring which afford 8 as white color solid, yield (99g, 90percent).
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 136, # PC, p. 1291 - 1297
  • 4
  • [ 90-96-0 ]
  • [ 1066-26-8 ]
  • [ 74-86-2 ]
  • [ 101597-25-5 ]
Reference: [1] Patent: EP994871, 2006, B1, . Location in patent: Page/Page column 13
  • 5
  • [ 90-96-0 ]
  • [ 74-86-2 ]
  • [ 101597-25-5 ]
Reference: [1] Annales de Chimie (Cachan, France), 1956, vol. <13> 1, p. 214,224
[2] Chemische Berichte, 1970, vol. 103, p. 2208 - 2224
[3] Organic Letters, 2014, vol. 16, # 8, p. 2236 - 2239
  • 6
  • [ 90-96-0 ]
  • [ 101597-25-5 ]
Reference: [1] Patent: US5411679, 1995, A,
[2] Patent: US5411679, 1995, A,
[3] European Journal of Pharmaceutics and Biopharmaceutics, 2013, vol. 85, # 3 PART B, p. 862 - 872
  • 7
  • [ 90-96-0 ]
  • [ 70277-75-7 ]
  • [ 101597-25-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1968, vol. 11, # 4, p. 749 - 752
  • 8
  • [ 90-96-0 ]
  • [ 1066-26-8 ]
  • [ 101597-25-5 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4289 - 4300
  • 9
  • [ 100-07-2 ]
  • [ 101597-25-5 ]
Reference: [1] European Journal of Pharmaceutics and Biopharmaceutics, 2013, vol. 85, # 3 PART B, p. 862 - 872
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