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[ CAS No. 223131-01-9 ] {[proInfo.proName]}

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Chemical Structure| 223131-01-9
Chemical Structure| 223131-01-9
Structure of 223131-01-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 223131-01-9 ]

CAS No. :223131-01-9 MDL No. :MFCD03844606
Formula : C12H23NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 229.32 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 223131-01-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 63.36
TPSA : 58.56 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) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.67
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 1.26
Consensus Log Po/w : 1.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.05
Solubility : 2.06 mg/ml ; 0.00898 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.553 mg/ml ; 0.00241 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.88
Solubility : 3.06 mg/ml ; 0.0133 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.05

Safety of [ 223131-01-9 ]

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 [ 223131-01-9 ]

* 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 [ 223131-01-9 ]
  • Downstream synthetic route of [ 223131-01-9 ]

[ 223131-01-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 24424-99-5 ]
  • [ 30134-98-6 ]
  • [ 223131-01-9 ]
YieldReaction ConditionsOperation in experiment
79% at 20℃; Di-tert-butyl dicarbonate (3.04 g, 13.9 mmol) was added to a stirred solution of ((1r,4r)-4-aminocyclohexyl)methanol (1.50 g, 11.6 mmol) in tetrahydrofuran (20 mL).
After stirring overnight at ambient temperature, the mixture was evaporated and partitioned between ethyl acetate and water.
The organic layer was separated, washed with water and brine, dried (MgSO4) and evaporated.
The residue was treated with hexanes and the suspension was filtered to give the title compound (2.11 g, 79percent) as a white solid.
LRMS (m/z): 228 (M-H)+.
1H NMR δ (DMSQ-d6): 0.84 - 0.95 (m, 2H), 1.05-1.18 (m, 2H), 1.20 - 1.29 (m, 2H), 1.40 (s, 9H), 1.71 - 1.80 (m, 3H), 3.14 (m, 1H), 3.21 (t, 2H), 4.41 (t, 1H), 6.73 (d, 1H).
Reference: [1] Patent: EP2554544, 2013, A1, . Location in patent: Paragraph 0161
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S309-S310,S311
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # 3, p. 293 - 307
[4] Patent: US2015/31674, 2015, A1, . Location in patent: Paragraph 0274
  • 2
  • [ 24424-99-5 ]
  • [ 61367-22-4 ]
  • [ 223131-01-9 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In dichloromethane at 20℃; ((cis)-4-aminocyclohexyl)methanol hydrochloride (20.0 g, 0.121 mol) was added to DCM (30 mL) and triethylamine (32 g, 0.316 mol) was added,Di-tert-butyl dicarbonate (32 g, 0.147 mol) was slowly added dropwise and stirred overnight at room temperature. LC-MS monitored that no raw material remained, and was concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (PE:EA=30:1) to give tert-butyl (cis)-4-(hydroxymethyl)cyclohexyl)carbamate ( 28g, yield 96percent).
Reference: [1] Patent: CN107793360, 2018, A, . Location in patent: Paragraph 0211; 0212; 0213
  • 3
  • [ 53292-90-3 ]
  • [ 223131-01-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2177 - 2180
[2] Patent: US2016/333021, 2016, A1, . Location in patent: Page/Page column 0432
  • 4
  • [ 1346527-75-0 ]
  • [ 223131-01-9 ]
Reference: [1] Patent: WO2005/95357, 2005, A2, . Location in patent: Page/Page column 109; 110
  • 5
  • [ 364385-64-8 ]
  • [ 223131-01-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 10, p. 3307 - 3319
  • 6
  • [ 3685-23-2 ]
  • [ 223131-01-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 10, p. 3307 - 3319
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2177 - 2180
  • 7
  • [ 62456-15-9 ]
  • [ 223131-01-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 10, p. 3307 - 3319
  • 8
  • [ 24424-99-5 ]
  • [ 223131-01-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2177 - 2180
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