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[ CAS No. 13490-69-2 ] {[proInfo.proName]}

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Chemical Structure| 13490-69-2
Chemical Structure| 13490-69-2
Structure of 13490-69-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13490-69-2 ]

CAS No. :13490-69-2 MDL No. :MFCD00167435
Formula : C11H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HDLQGISFYDYWFJ-JTQLQIEISA-N
M.W : 178.23 Pubchem ID :7233172
Synonyms :

Calculated chemistry of [ 13490-69-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.41
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) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 3.0
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 2.58
Log Po/w (SILICOS-IT) : 2.26
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.187 mg/ml ; 0.00105 mol/l
Class : Soluble
Log S (Ali) : -3.45
Solubility : 0.0636 mg/ml ; 0.000357 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.64
Solubility : 0.408 mg/ml ; 0.00229 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 13490-69-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13490-69-2 ]

* 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 [ 13490-69-2 ]
  • Downstream synthetic route of [ 13490-69-2 ]

[ 13490-69-2 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 3508-94-9 ]
  • [ 13490-69-2 ]
YieldReaction ConditionsOperation in experiment
37%
Stage #1: With (<i>S</i>)-1-phenyl-ethylamine In ethanol; waterReflux
Stage #2: With sulfuric acid In ethyl acetate at 0℃;
2-Isopropylphenylaceticacid (8.91 g), (+)-α-phenylethylamine (6.45 mL), and 63percentaqueous ethanol (193 mL) were refluxed and allowed to cool slowly. The resultingsalt was recrystallized three times from 63percent aqueous ethanol. The salt was treatedwith 10percent sulfuric acid at 0 °C, extracted with ethyl acetate, dried, and concentrated toyield 3.52 g (Yield is 39percent) of (R)-(-)-2-isopropylphenylacetic acid, [α]25D -58.6°(CHCl3, c = 0.02).
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 42 - 51
[2] Tetrahedron, 1971, vol. 27, p. 1173 - 1184
[3] Chemical Communications, 2006, # 34, p. 3600 - 3602
  • 2
  • [ 13491-00-4 ]
  • [ 13490-69-2 ]
YieldReaction ConditionsOperation in experiment
99% With sulfuric acid In water A suspension of intermediate 13 (14.7g, 49MMOL) in water (100ML) was acidified with 10percent aqueous sulphuric acid and extracted with DICHLOROMETHANE (3 x 100ML). The organic extracts were dried over magnesium sulphate and concentrated in vacuo. Cooling the residue to 0 DEGC afforded the title compound as a white SOLID (8. 65g, 99percent); 1 H NMR (250MHz, CDCI3) : 0.70 (3H, d, 6.7Hz), 1.08 (3H, d, 6.5Hz), 2.33 (1H, m), 3.14 (1H, d, 10.6Hz), 7.24-7. 33 (5H, M) ; [A] 23. 9D= +65. 2° (c=1 in MEOH).
Reference: [1] Patent: WO2005/14575, 2005, A1, . Location in patent: Page/Page column 20
  • 3
  • [ 4412-08-2 ]
  • [ 13490-69-2 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 25, p. 7876 - 7878
  • 4
  • [ 222021-01-4 ]
  • [ 13490-69-2 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 9, p. 1637 - 1640
[2] Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 7091 - 7097
  • 5
  • [ 124931-92-6 ]
  • [ 13490-69-2 ]
Reference: [1] Journal of the American Chemical Society, 1995, vol. 117, # 49, p. 12159 - 12171
  • 6
  • [ 75-30-9 ]
  • [ 103-82-2 ]
  • [ 13490-69-2 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11936 - 11939
  • 7
  • [ 4412-08-2 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Bioscience, Biotechnology, and Biochemistry, 1994, vol. 58, # 11, p. 2071 - 2072
[2] Bioscience, Biotechnology, and Biochemistry, 1994, vol. 58, # 11, p. 2071 - 2072
[3] Tetrahedron Asymmetry, 2004, vol. 15, # 14, p. 2299 - 2306
[4] Organic Letters, 2013, vol. 15, # 14, p. 3722 - 3725
  • 8
  • [ 3508-94-9 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7436 - 7441
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 23, p. 2704 - 2708
  • 9
  • [ 5558-29-2 ]
  • [ 13490-69-2 ]
  • [ 13490-79-4 ]
Reference: [1] Tetrahedron Asymmetry, 2000, vol. 11, # 5, p. 1123 - 1135
  • 10
  • [ 103-82-2 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 14, p. 3722 - 3725
  • 11
  • [ 300-57-2 ]
  • [ 13490-69-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 16, p. 1847 - 1850
  • 12
  • [ 134837-45-9 ]
  • [ 13490-69-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 16, p. 1847 - 1850
  • 13
  • [ 134837-46-0 ]
  • [ 13490-69-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 16, p. 1847 - 1850
  • 14
  • [ 134837-57-3 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 16, p. 1847 - 1850
  • 15
  • [ 72615-27-1 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
  • [ 127641-47-8 ]
  • [ 143838-44-2 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 50, p. 7053 - 7056
[2] Tetrahedron Letters, 1989, vol. 30, # 50, p. 7053 - 7056
  • 16
  • [ 103-82-2 ]
  • [ 75-26-3 ]
  • [ 13490-69-2 ]
Reference: [1] Journal of Organic Chemistry, 1967, vol. 32, p. 2797 - 2803
  • 17
  • [ 4412-08-2 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Bioscience, Biotechnology, and Biochemistry, 1994, vol. 58, # 11, p. 2071 - 2072
[2] Bioscience, Biotechnology, and Biochemistry, 1994, vol. 58, # 11, p. 2071 - 2072
[3] Tetrahedron Asymmetry, 2004, vol. 15, # 14, p. 2299 - 2306
[4] Organic Letters, 2013, vol. 15, # 14, p. 3722 - 3725
  • 18
  • [ 3508-94-9 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7436 - 7441
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 23, p. 2704 - 2708
  • 19
  • [ 103-82-2 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 14, p. 3722 - 3725
  • 20
  • [ 134837-57-3 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 16, p. 1847 - 1850
  • 21
  • [ 72615-27-1 ]
  • [ 13490-69-2 ]
  • [ 13491-13-9 ]
  • [ 127641-47-8 ]
  • [ 143838-44-2 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 50, p. 7053 - 7056
[2] Tetrahedron Letters, 1989, vol. 30, # 50, p. 7053 - 7056
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