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[ CAS No. 54622-95-6 ] {[proInfo.proName]}

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Chemical Structure| 54622-95-6
Chemical Structure| 54622-95-6
Structure of 54622-95-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54622-95-6 ]

CAS No. :54622-95-6 MDL No. :MFCD10039832
Formula : C9H14O6 Boiling Point : -
Linear Structure Formula :- InChI Key :BTFKDZSYIKUCGF-BYPJNBLXSA-N
M.W : 218.20 Pubchem ID :10932896
Synonyms :

Calculated chemistry of [ 54622-95-6 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.3
TPSA : 74.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : -0.18
Log Po/w (WLOGP) : -0.04
Log Po/w (MLOGP) : -0.68
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : 0.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.95
Solubility : 24.6 mg/ml ; 0.113 mol/l
Class : Very soluble
Log S (Ali) : -0.92
Solubility : 26.1 mg/ml ; 0.119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.17
Solubility : 321.0 mg/ml ; 1.47 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.16

Safety of [ 54622-95-6 ]

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 [ 54622-95-6 ]

* 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 [ 54622-95-6 ]
  • Downstream synthetic route of [ 54622-95-6 ]

[ 54622-95-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 4099-85-8 ]
  • [ 54622-95-6 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In water; ethyl acetate at 0℃; for 0.5 h; Inert atmosphere
Stage #2: With hydrogenchloride; sodium chlorite In water; ethyl acetate at 20℃; for 7 h;
KBr (1.70 g, 14.7 mmol) and TEMPO (0.383 g, 2.45 mmol) were added to a solution of 2 (10.0 g, 49.0 mmol) in EtOAc (100 mL), followed by dropwise addition of NaOCl (12percent, 39.5 mL, 63.7 mmol) over 30 min at 0 °C. Then, the pH was adjusted to 2 by the addition of 35percent HCl, followed by the addition of 25percent aq NaClO2 (5.76 g, 63.7 mmol) over 30 min maintaining r.t. Stirring was continued until completion of the reaction after 7 h. After adjusting the pH to 2–3, the product was extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered, and the solvent was removed in vacuo to give the crude product. Recrystallization from hot CH2Cl2 with n-hexane gave a white solid; yield: 10.68 g (quant.); mp 128.5–129.5 °C (Lit.27b mp 129–131 °C); [α]D20.5 –67.29 (c 2.47, CHCl3).1H NMR (CDCl3, 400 MHz): δ = 10.69 (s, 1 H), 5.20 (d, J = 6.3 Hz, 1 H)5.09 (s, 1 H), 4.69 (s, 1 H), 4.59 (d, J = 6.0 Hz, 1 H), 3.45 (s, 3 H), 1.50(s,3 H), 1.34 (s, 3 H).
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 20, p. 5246 - 5252
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4299 - 4302
[3] Tetrahedron, 1991, vol. 47, # 4-5, p. 715 - 724
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 5168,5173
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053
  • 2
  • [ 532-20-7 ]
  • [ 54622-95-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4299 - 4302
  • 3
  • [ 67814-68-0 ]
  • [ 54622-95-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053
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