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[ CAS No. 164470-64-8 ] {[proInfo.proName]}

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Chemical Structure| 164470-64-8
Chemical Structure| 164470-64-8
Structure of 164470-64-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 164470-64-8 ]

CAS No. :164470-64-8 MDL No. :MFCD01074693
Formula : C23H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :JRHUROPSUJVMNH-UHFFFAOYSA-N
M.W : 373.40 Pubchem ID :2756083
Synonyms :

Calculated chemistry of [ 164470-64-8 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.13
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 105.23
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : 4.08
Log Po/w (WLOGP) : 4.27
Log Po/w (MLOGP) : 3.48
Log Po/w (SILICOS-IT) : 3.94
Consensus Log Po/w : 3.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.74
Solubility : 0.00681 mg/ml ; 0.0000182 mol/l
Class : Moderately soluble
Log S (Ali) : -5.37
Solubility : 0.00158 mg/ml ; 0.00000423 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.34
Solubility : 0.0000171 mg/ml ; 0.0000000457 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.41

Safety of [ 164470-64-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 164470-64-8 ]

* 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 [ 164470-64-8 ]
  • Downstream synthetic route of [ 164470-64-8 ]

[ 164470-64-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 56-91-7 ]
  • [ 71989-31-6 ]
  • [ 164470-64-8 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 2 h; (4-aminomethyl)-benzoic acid (4.9 g, 1. 1 equiv. ) was dissolved in 5percent NaHCO3 150 ml in water and stirred. N- (9- Fluorenylmethoxycarbonyl) -L-proline (Fmoc, 1 equiv. , lOg) was dissolved in an equivalent amount of dioxane and added. The reaction was allowed to stir at room temperature. After two hours, 10percent citric acid in water 75 ml was added. A white solid precipitated upon addition. The solid was washed filtered and washed with hexane. The solid was dissolved in THF and allowed to dry overnight over MGSO. The following day, the solution was filtered, crystallized from THF and hexane, and placed under a drying vacuum (90percent yield). ESIMS: (M+H) + Calcd, 373.1 ; Found, 374.1.
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 39, p. 11804 - 11805
[2] Patent: WO2004/99106, 2004, A2, . Location in patent: Page 18-19; 27-28
  • 2
  • [ 56-91-7 ]
  • [ 82911-69-1 ]
  • [ 164470-64-8 ]
YieldReaction ConditionsOperation in experiment
23% With sodium hydrogencarbonate In water; acetone at 20℃; 4-(Aminomethyl)benzoic acid (304 mg, 2.0 mmol) was stirred in 10percent Sodium hydrogencarbonate (sat aq, 10 ml). N-(9-Fluorenylmethoxycarbonyloxy)succinimide (680 mg, 2.0 mmol) and acetone (10 ml) was added and thick suspension was formed. Water (10 ml) was added to give an almost clear mixture that was stirred at room temperature over week-end. The mixture was washed with dichloromethane (a thick precipitate was formed in the water layer). The water layer was acidified with HCI (1 M) and extracted with dichloromethane (the precipitate moved into the dichloromethane layer). The precipitate was filtered off, dissolved in acetone and the insoluble material was filtered off. This latter filtrate was evaporated and dried on pump to yield a pure product (174 mg, 0.466 mmol, 23 percent). H NMR (400 MHz, DMSO-cfe) δ ppm 4.25 (m, 3 H) 4.38 (d, J^6.6 Hz, 2 H) 7.26 - 7.46 (m, 6 H) 7.70 (d, J=7.6 Hz, 2 H) 7.81 - 7.99 (m, 5 H) 12.85 (br. s., 1 H). 3C NMR (101 MHz, DMSO-cfe) δ ppm 43.55, 46.82, 65.33, 120.1 1 , 125.14, 126.96, 127.03, 127.59, 129.37, 140.78, 143.86, 144.90, 156.41 , 167.19.
Reference: [1] Organic letters, 2001, vol. 3, # 26, p. 4239 - 4242
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 528 - 530
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 1, p. 161 - 175
[4] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4423 - 4427
[5] Patent: WO2015/63694, 2015, A1, . Location in patent: Page/Page column 39
[6] Chemical Communications, 2010, vol. 46, # 8, p. 1221 - 1223
[7] Organic Process Research and Development, 2001, vol. 5, # 4, p. 445 - 449
[8] Biological Chemistry, 2015, vol. 396, # 1, p. 45 - 52
  • 3
  • [ 56-91-7 ]
  • [ 28920-43-6 ]
  • [ 164470-64-8 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 16, p. 6518 - 6524
[2] Tetrahedron, 1998, vol. 54, # 50, p. 15063 - 15086
[3] Organic Letters, 2008, vol. 10, # 10, p. 1881 - 1884
[4] Russian Journal of General Chemistry, 2010, vol. 80, # 12, p. 2572 - 2589
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 873 - 879
[6] Patent: US9422239, 2016, B1, . Location in patent: Page/Page column 89
  • 4
  • [ 56-91-7 ]
  • [ 497-19-8 ]
  • [ 164470-64-8 ]
Reference: [1] Patent: US2003/187027, 2003, A1,
[2] Patent: US2004/72849, 2004, A1,
  • 5
  • [ 56-91-7 ]
  • [ 164470-64-8 ]
Reference: [1] Patent: US6191171, 2001, B1,
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