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[ CAS No. 21658-35-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 21658-35-5
Chemical Structure| 21658-35-5
Chemical Structure| 21658-35-5
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Product Details of [ 21658-35-5 ]

CAS No. :21658-35-5 MDL No. :MFCD00092742
Formula : C13H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IZOYTDIICIICBE-UHFFFAOYSA-N
M.W : 200.23 Pubchem ID :238676
Synonyms :

Calculated chemistry of [ 21658-35-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.15
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.3
TPSA : 37.3 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) : -5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 3.34
Log Po/w (WLOGP) : 2.86
Log Po/w (MLOGP) : 2.92
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 2.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.48
Solubility : 0.0662 mg/ml ; 0.00033 mol/l
Class : Soluble
Log S (Ali) : -3.8
Solubility : 0.0317 mg/ml ; 0.000158 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.26
Solubility : 0.011 mg/ml ; 0.0000548 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.1

Safety of [ 21658-35-5 ]

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

Application In Synthesis of [ 21658-35-5 ]

* 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 [ 21658-35-5 ]
  • Downstream synthetic route of [ 21658-35-5 ]

[ 21658-35-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 21658-35-5 ]
  • [ 6342-87-6 ]
YieldReaction ConditionsOperation in experiment
80% at 20℃; In a flask equipped with a mechanical stirrer to the Eaton's reagent prepared from 165.0 g of P4O10 and 840 ml of methanesulfonic acid 144.0 g (ca. 720 mmol) of 3-(naphthalen-2- yl)propanoic acid was added portionwise at room temperature. The formed mixture was stirred overnight, then poured into 2 L of ice-cold water. Crude product was extracted with 3 x 500 ml of dichloromethane. The combined extract was washed with aqueous K2CO3, dried over Na2S04, and then evaporated to dryness. The residue was subjected to flash chromatography using 600 ml of silica gel 60 (40-653 urn) and mixture of hexane and dichloromethane in the ratio 1 :1 as eluent to give 105.0 g (80percent) of the title product as a brownish solid. Anal. calc. for C13H10O: C, 85.69; H, 5.53. Found: C, 85.98; H, 5.75. 1H NMR (CDCIs): 5 9.12 (d, J = 8.5 Hz, 1 H), 7.93 (d, J = 8.3 Hz, 1 H), 7.81 (d, J = 8.1 Hz, 1 H), 7.61 (ddd, J = 8.3 Hz, J = 7.1 Hz, J = 1.2 Hz, 1 H), 7.50 (ddd, J = 8.1 Hz, J = 7.1 Hz, J = 1 .0 Hz, 1 H), 7.39 (d, J = 8.3 Hz, 1 H), 3.12-3.04 (m, 2H), 2.75-2.65 (m, 2H). 13C{1H} NMR (CDCIs): 5207.26, 158.26, 135.47, 132.41 , 130.81 , 129.23, 128.65, 127.90, 126.39, 123.87, 123.76, 36.73, 25.99
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 14, p. 3214 - 3222
[2] Chemistry - A European Journal, 2015, vol. 21, # 37, p. 13052 - 13057
[3] Patent: WO2017/118617, 2017, A1, . Location in patent: Page/Page column 20
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 1845 - 1848
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 10, p. 1015 - 1019
[6] Journal of Organic Chemistry, 1984, vol. 49, # 1, p. 207 - 209
[7] Tetrahedron Letters, 2012, vol. 53, # 1, p. 15 - 18
  • 2
  • [ 21658-35-5 ]
  • [ 7646-78-8 ]
  • [ 6342-87-6 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 1098,1100, 1110[2] Journal of the Chemical Society, 1934, p. 365,366
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