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[ CAS No. 183673-66-7 ] {[proInfo.proName]}

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Chemical Structure| 183673-66-7
Chemical Structure| 183673-66-7
Structure of 183673-66-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 183673-66-7 ]

CAS No. :183673-66-7 MDL No. :MFCD01318741
Formula : C26H30N2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :BOFOACPQHWDRLH-UHFFFAOYSA-N
M.W : 466.53 Pubchem ID :2734399
Synonyms :

Calculated chemistry of [ 183673-66-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.42
Num. rotatable bonds : 9
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 130.07
TPSA : 105.17 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.25
Log Po/w (XLOGP3) : 3.88
Log Po/w (WLOGP) : 4.0
Log Po/w (MLOGP) : 2.8
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 3.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.84
Solubility : 0.00668 mg/ml ; 0.0000143 mol/l
Class : Moderately soluble
Log S (Ali) : -5.79
Solubility : 0.000764 mg/ml ; 0.00000164 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.95
Solubility : 0.000528 mg/ml ; 0.00000113 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.18

Safety of [ 183673-66-7 ]

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

Application In Synthesis of [ 183673-66-7 ]

* 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 [ 183673-66-7 ]
  • Downstream synthetic route of [ 183673-66-7 ]

[ 183673-66-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 183673-66-7 ]
  • [ 406235-17-4 ]
  • [ 161529-14-2 ]
Reference: [1] Patent: US2002/55631, 2002, A1,
[2] Patent: US2002/86887, 2002, A1,
  • 2
  • [ 28920-43-6 ]
  • [ 183673-71-4 ]
  • [ 183673-66-7 ]
YieldReaction ConditionsOperation in experiment
42% With sodium carbonate In tetrahydrofuran at 0 - 25℃; for 12 h; 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert- butoxycarbonyl)piperidine-4-carboxylic acid (Scheme 1, compound 8) [0225] A solution of 4-amino-1 -(terf-butoxycarbonyl)piperidine-4- carboxylic acid (5 g, 20.5 mmol) in THF (300 mL) and Na2CO3 (6.45 g, 61 .5 mmol, 3.0 eq in 64.5 mL of water) was cooled to 0°C before the dropwise addition of a solution of Fmoc chloride (5.3 g, 30.7 mmol, 1 .5 eq) in THF (30 mL). The resulting mixture was slowly warmed to 25°C and stirred for an additional 12 hours. Upon completion, the reaction contents were carefully acidified with HCI (1 M), and the crude material was extracted with EtOAc (three times). The combined organic layers were dried (Na2SO4), concentrated, and the crude material was purified by combiflash 0 to 10percent MeOH in DCM to provide 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1 -(te/t- butoxycarbonyl)piperidine-4-carboxylic acid (Scheme 1 , compound 8) (4.02 g, 42percent yield). [0226] 1 H NMR (400 MHz, Ch lore-form -c/) δ 7.75 (d, J = 7.5 Hz, 2H), 7.57 (d, J = 7.5 Hz, 2H), 7.45-7.34 (m, 2H), 7.30 (td, J = 6.9, 6.3, 1 .4 Hz, 2H), 4.68-4.26 (m, 2H), 4.19 (t, J = 6.5 Hz, 1 H), 3.96-3.65 (m, 3H), 3.08 (s, 2H), 1 .91 -1 .77 (m, 2H), 1 .48 (s, 9H). 13C NMR (101 MHz, CDCI3) 177.19, 154.73, 143.67, 141 .32, 127.72, 127.08, 124.95, 1 19.97, 80.06, 67.90, 66.86, 57.49, 47.19, 31 .98, 28.42, 25.57. HRMS (m/z): [M+] cald for C26H30N2O6, 466.53, found 466.2
Reference: [1] Organic Syntheses, 2005, vol. 81, p. 213 - 224
[2] Patent: WO2015/184349, 2015, A2, . Location in patent: Paragraph 0225-0226
  • 3
  • [ 82911-69-1 ]
  • [ 183673-71-4 ]
  • [ 183673-66-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 18, p. 5694 - 5706
  • 4
  • [ 40064-34-4 ]
  • [ 183673-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
[2] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
  • 5
  • [ 24424-99-5 ]
  • [ 183673-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
  • 6
  • [ 79099-07-3 ]
  • [ 183673-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
  • 7
  • [ 13625-39-3 ]
  • [ 183673-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
  • 8
  • [ 183673-70-3 ]
  • [ 183673-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
  • 9
  • [ 183673-68-9 ]
  • [ 183673-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
  • 10
  • [ 102774-86-7 ]
  • [ 183673-71-4 ]
  • [ 183673-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7650 - 7651
  • 11
  • [ 183673-66-7 ]
  • [ 368866-09-5 ]
Reference: [1] Patent: WO2011/153588, 2011, A1, . Location in patent: Page/Page column 49
[2] ChemBioChem, 2016, vol. 17, # 2, p. 137 - 140
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