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[ CAS No. 101555-63-9 ] {[proInfo.proName]}

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Chemical Structure| 101555-63-9
Chemical Structure| 101555-63-9
Structure of 101555-63-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 101555-63-9 ]

CAS No. :101555-63-9 MDL No. :MFCD00235899
Formula : C21H21NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :CKLAZLINARHOTG-LJQANCHMSA-N
M.W : 351.40 Pubchem ID :6958378
Synonyms :

Calculated chemistry of [ 101555-63-9 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 101.49
TPSA : 66.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : 3.72
Log Po/w (WLOGP) : 3.49
Log Po/w (MLOGP) : 3.0
Log Po/w (SILICOS-IT) : 2.9
Consensus Log Po/w : 3.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.37
Solubility : 0.0149 mg/ml ; 0.0000423 mol/l
Class : Moderately soluble
Log S (Ali) : -4.82
Solubility : 0.00538 mg/ml ; 0.0000153 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.88
Solubility : 0.00466 mg/ml ; 0.0000133 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.75

Safety of [ 101555-63-9 ]

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 [ 101555-63-9 ]

* 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 [ 101555-63-9 ]
  • Downstream synthetic route of [ 101555-63-9 ]

[ 101555-63-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 102774-86-7 ]
  • [ 3105-95-1 ]
  • [ 101555-63-9 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In 1,4-dioxane at 20℃; Synthesis of building blocks A Synthesis of (S)-1 -(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid A solution of the L-pipecolic acid (3.6g, 38.7 mmol) in 40ml of 10percent sodium carbonate was dissolved in round bottom flask and allowed to stir for 5 min at rt. To this solution was added F-moc succinamide (8.5g, 34.8 mmol) dissolved in 35 ml dioxane and the reaction was stirred overnight. After overnight stirring water was added and the aqueous layer was extracted with ethyl acetate. The aqueous layer was made acidic (pH-2) by addition of concentrated HCI. The acidic layer was extracted with ethyl acetate (3x 40ml). The organic phase was washed with 1 N HCI followed by brine, dried over MgSO4 and concentrated under vacuo to yield a oily colorless liquid. The oily liquid was dissolved in ether and cooled to get fluffy white solid which was washed with hexane and dried to yield (S)-1 -(((9H-fluoren-9- yl)methoxy)carbonyl)piperidine-2-carboxylic acid ( 8.2g, 38.7mmol, 83percent). TLC (Hexane:EtOAc: TFA 1 : 1 : 0.2): RF = 0.60 HPLC (Gradient A) retention time= 24.6-24.8 min 1 H NMR (300 MHz, CDCI3) 5=1 .28-1 .53 (m, 2H), 1 .69-1 .82 (m, 3H), 2.19-2.37 (m, 1 H), 3.15 (t, 1 H, J= 13.2Hz), 4.05-4.33 (m, 2H), 4.37-4.49 (m, 2H), 4.76-5.05(m, 1 H), 7.28-7.41 (m, 4H), 7.55-7.62 (m, 2H), 1 .77 (s, 2H). 13C NMR (75 MHz, CDCI3) δ= 20.72, 24.70, 26.55, 41 .94, 47.25, 54.19, 67.86, 1 19.97, 125.08, 127.07, 127.68, 141 .33, 143.89, 156.65, 177.36 MS (ESI) m/z 352.66 [M + H] \ calculated 352.40 [M + H] +.
Reference: [1] Patent: WO2013/91900, 2013, A1, . Location in patent: Page/Page column 41
  • 2
  • [ 28920-43-6 ]
  • [ 3105-95-1 ]
  • [ 101555-63-9 ]
YieldReaction ConditionsOperation in experiment
1.41 g With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; for 16 h; To a stirred mixture of (S)-piperidine-2-carboxylic acid (1.0 g, 7.75 mmol) and Na2C03 (1.65 g, 15.50 mmol) in water (10 mL) was added a solution of FMOC-C1 (3.0 g, 11.63 mmol) in 1,4-dioxane (10 mL) dropwise at 0°C and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (50 mL) and washed with MTBE (25 mL). The aqueous layer was acidified with 1M aqueous HC1 (10 mL) to pH 2 and extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with brine solution (50 mL), dried over anhydrous a2S04, filtered and concentrated to afford the title compound (1.41 g) as an off-white solid. The crude product was used in the next step without purification
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1111 - 1115
[2] Journal of the American Chemical Society, 2006, vol. 128, # 11, p. 3838 - 3847
[3] Patent: WO2013/148478, 2013, A1, . Location in patent: Page/Page column 23
  • 3
  • [ 82911-69-1 ]
  • [ 3105-95-1 ]
  • [ 101555-63-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 5, p. 1059 - 1063
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4114 - 4122
  • 4
  • [ 88744-04-1 ]
  • [ 3105-95-1 ]
  • [ 101555-63-9 ]
Reference: [1] Synthesis, 1986, # 4, p. 303 - 305
  • 5
  • [ 28920-43-6 ]
  • [ 15912-30-8 ]
  • [ 101555-63-9 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 16, p. 4394 - 4400
  • 6
  • [ 4043-87-2 ]
  • [ 101555-63-9 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 16, p. 6686 - 6693
  • 7
  • [ 82911-69-1 ]
  • [ 101555-63-9 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 16, p. 6686 - 6693
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