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[ CAS No. 60031-08-5 ] {[proInfo.proName]}

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Chemical Structure| 60031-08-5
Chemical Structure| 60031-08-5
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Product Details of [ 60031-08-5 ]

CAS No. :60031-08-5 MDL No. :MFCD02179295
Formula : C10H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BIABIACQHKYEEB-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :12341286
Synonyms :

Calculated chemistry of [ 60031-08-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.45
TPSA : 54.37 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : 1.51
Log Po/w (MLOGP) : 1.2
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.94 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (Ali) : -1.93
Solubility : 2.08 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.574 mg/ml ; 0.00326 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 60031-08-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 60031-08-5 ]

* 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 [ 60031-08-5 ]
  • Downstream synthetic route of [ 60031-08-5 ]

[ 60031-08-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 38628-51-2 ]
  • [ 60031-08-5 ]
YieldReaction ConditionsOperation in experiment
90% at 180℃; for 1 h; Neat (no solvent) 6-Carboxy-1-indanone used as the starting material of example 206 was prepared according to the following procedure: 3- (4-carboxyphenyl) propionic acid (5 g, 0.026 mol), frash AICI3 (25 g, 7.2 eq, 0.187 mol), and NaCI (2.5 g, 10percent w/w of AICI3 used) were loaded into a 100 mL flask fitted with a condenser and internal thermometer going to the bottom of the flask. The flask was shaken briefly to mix the solids, then heated in an oil bath set to 190 °C. Internal temperature was held at or above 180° C for 1 h (reaction will fuse to form a dark brown liquid), then the mixture was cooled, and washed with water into a 2000 mL beaker containing ice. 180 mL of 6 M HCI and 250 mL of EtOAc were added. The layers were separated and the aqueous layer extracted with EtOAc (3 x 200 mL). Combined organic layers were washed with 2 M HCI, water, and brine, dried with MgS04, filtered and concentrated in vacuo to yield 6-carboxy-1-indanone (4.10 g, 90percent) as a light brown solid directly used for the next step synthesis.
90%
Stage #1: at 190℃; for 2 h;
Stage #2: With hydrogenchloride In water; ethyl acetate at 25℃; Cooling with ice bath
Step 1:
A mixture of compound 1 (82.4 mmol, 1.0 eq.), AlCl3 (593.8 mmol, 7.2 eq.) and NaCl (10percent w/w of AlCl3 used) was heated at 190° C. for 2 h.
The reaction mixture was cooled to 25° C., the tacky mass was dissolved in ice-cold water and the solution was shaken with crushed ice in a 5 l glass beaker.
A mixture of 600 ml of a 6 N HCl and 750 ml of ethyl acetate was added to the reaction mixture.
The organic phase was separated off and the aqueous phase was extracted with ethyl acetate (3*650 ml).
The combined organic phases were washed with 2 M HCl (100 ml), water (2*100 ml) and sat. NaCl solution (100 ml) and dried over sodium sulfate.
The solvent was concentrated in vacuo in order to obtain the desired product 2. Yield: 90percent
Reference: [1] Patent: WO2005/87236, 2005, A1, . Location in patent: Page/Page column 39
[2] Patent: US2010/249095, 2010, A1, . Location in patent: Page/Page column 68-69
[3] Tetrahedron, 1995, vol. 51, # 1, p. 203 - 216
[4] Journal of the Chemical Society, 1956, p. 4647,3652
[5] Patent: US2012/71461, 2012, A1, . Location in patent: Page/Page column 60
  • 2
  • [ 866848-94-4 ]
  • [ 124-38-9 ]
  • [ 60031-08-5 ]
Reference: [1] Patent: WO2005/95387, 2005, A1, . Location in patent: Page/Page column 60
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