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[ CAS No. 16801-63-1 ] {[proInfo.proName]}

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Chemical Structure| 16801-63-1
Chemical Structure| 16801-63-1
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Product Details of [ 16801-63-1 ]

CAS No. :16801-63-1 MDL No. :MFCD06658393
Formula : C14H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VHXBIBFCJISKFA-UHFFFAOYSA-N
M.W :247.29 Pubchem ID :14615292
Synonyms :

Calculated chemistry of [ 16801-63-1 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.62
TPSA : 55.4 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) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 2.27
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.27
Consensus Log Po/w : 2.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 1.13 mg/ml ; 0.00455 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.882 mg/ml ; 0.00357 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.87
Solubility : 0.0331 mg/ml ; 0.000134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.16

Safety of [ 16801-63-1 ]

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 [ 16801-63-1 ]

* 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 [ 16801-63-1 ]
  • Downstream synthetic route of [ 16801-63-1 ]

[ 16801-63-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 27489-63-0 ]
  • [ 16801-63-1 ]
YieldReaction ConditionsOperation in experiment
72% With Jones reagent In acetone at 0℃; for 0.5 h; [00695] Synthesis of compound 120.3. To a solution of compound 120.2 (7.0 g, 28.08 mmol, 1.00 equiv) in acetone (100 mL) was added Jones reagent (-10 mL) dropwise at 0 °C. The reaction was monitored by TLC. After stirring for 30 minutes, reaction was quenched with saturated aqueous NaHSOs and extracted with 3 x 100 mL of EtOAc. Combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 5.0 g (72percent) of compound 120.3 as a white solid.
72% With Jones reagent In acetone at 0℃; for 0.5 h; Synthesis of compound 7.3. To a solution of compound 7.2 (7.0 g, 28.08 mmol, 1.00 equiv) in acetone (100 mL) was added dropwise Jones reagent (-10 mL) at 0°C. Reaction was monitored by TLC and stirred for 30 min. Reaction was quenched with saturated aqueous NaHS03, extracted with 3 x 100 mL of EtOAc. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 5.0 g (72percent) of benzyl N-(4-oxocyclohexyl)carbamate, 7.3 as a white solid.
71% With pyridinium chlorochromate In diethyl ether; dichloromethane (2)
To 1000 ml of dichloromethane suspension containing 25.9 g of pyridinium chlorochromate (PCC) was added dropwise under ice-cooling a mixture of 15 g of N-benzyloxycarbonyl-trans-4-aminocyclohexanol and 1000 ml of dichloromethane.
The resulting mixture was stirred at room temperature for 4 hours.
Then, diethyl ether was added to the reaction mixture and insoluble materials were removed by filtration from the mixture.
The filtrate was condensed and the residue was purified by silica gel column chromatography (solvent; chloroform:methanol=10:1) to give 10.562 g of N-benzyloxycarbonyl-4-aminocyclohexanone (yield: 71percent, melting point: 65°-69° C.).
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 6, p. 3005 - 3009
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 10, p. 3387 - 3402
[3] Synthetic Communications, 1990, vol. 20, # 7, p. 1073 - 1082
[4] Patent: WO2014/194242, 2014, A2, . Location in patent: Paragraph 00693; 00695
[5] Patent: WO2015/164374, 2015, A1, . Location in patent: Paragraph 00288; 00290
[6] Patent: US5849732, 1998, A,
[7] Journal of Organic Chemistry, 1968, vol. 33, # 8, p. 3182 - 3187
[8] Journal of Materials Chemistry, 2011, vol. 21, # 18, p. 6677 - 6682
  • 2
  • [ 27489-63-0 ]
  • [ 16801-63-1 ]
YieldReaction ConditionsOperation in experiment
90.3% With 9-benzyl-9-norazaadamantane N-oxyl; di-isopropyl azodicarboxylate; acetic acid In dichloromethane for 8 h; Reflux trans-4-Carbobenzyloxyaminocyclohexanol (119.2 mg, 0.478 mmol) was oxidized in the same manner as that described in Example 8, (a) (except that Nor-AZADO was used at 3 mol percent, and DIAD was used in an amount of 1.1 equivalents) to obtain the objective compound (106.8 mg; yield, 90.3percent). The spectrum data were found to be the same as those obtained in Example 6, (m). A solution of 4-phenylbutan-2-ol (97.7 mg, 0.651 mmol), Nor-AZADO (0.90 mg, 6.51 µmol, 1 molpercent) and acetic acid (37 µl, 0.651 mmol) in dichloromethane (0.65 ml) was added with DIAD (128 µl, 0.651 mmol, 1 equivalent), and the mixture was stirred for 8 hours under reflux by heating. The reaction mixture was added with saturated aqueous sodium carbonate (2 ml), and the mixture was extracted with dichloromethane. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the objective compound (95.1 mg; yield, 99percent). The spectrum data were found to be the same as those obtained in Example 5, (b).
78% With chromium(VI) oxide In acetic acid at 20℃; for 24 h; To a stirred solution of trans-4-benzyloxycarbonylaminocyclohexanol (21.5 g, 86.3 mmol) in acetic acid (160 mL) at room temperature under nitrogen was added chromium trioxide (8.63 g, 86.3 mmol).
After 1 d, the reaction mixture was evaporated under vacuum to yield a residue.
The residue was suspended in acetone and filtered through a plug of Celite.(R)..
The filtrate was evaporated to obtain a green solid.
The green solid was purified by silica gel chromatography (eluted with 5percent methanol in methylene chloride) to obtain the title compound (16.65 g, 78percent) as an off-white solid. 13C NMR (400 MHz, CDCl3) δ 209.6, 155.8, 136.2, 128.5, 128.2, 128.1, 66.8, 47.9, 38.8, 32.1. 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 5H), 5.09 (s, 2H), 4.84 (br s, 1H), 3.97 (s, 1H), 2.38 (m, 4H), 2.20 (m, 2H), 1.68 (m, 2H). HPLC/MS [M+H]+, 248.
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 48, p. 12624 - 12627[2] Angew. Chem., 2013, vol. 125, # 48, p. 12856 - 12859,4
[3] Chemistry - An Asian Journal, 2015, vol. 10, # 4, p. 1004 - 1009
[4] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10256 - 10268
[5] Patent: EP2594550, 2013, A1, . Location in patent: Paragraph 0101; 0102
[6] Patent: US2006/111338, 2006, A1, . Location in patent: Page/Page column 29
[7] Organic Letters, 2013, vol. 15, # 5, p. 992 - 995
[8] Chemical and Pharmaceutical Bulletin, 2011, vol. 59, # 12, p. 1570 - 1573
[9] Patent: US2006/63791, 2006, A1, . Location in patent: Page/Page column 10
  • 3
  • [ 6850-65-3 ]
  • [ 16801-63-1 ]
Reference: [1] Synthetic Communications, 1990, vol. 20, # 7, p. 1073 - 1082
[2] Journal of Organic Chemistry, 1968, vol. 33, # 8, p. 3182 - 3187
[3] Journal of Materials Chemistry, 2011, vol. 21, # 18, p. 6677 - 6682
[4] Patent: WO2014/194242, 2014, A2,
[5] Patent: WO2015/164374, 2015, A1,
  • 4
  • [ 501-53-1 ]
  • [ 16801-63-1 ]
Reference: [1] Synthetic Communications, 1990, vol. 20, # 7, p. 1073 - 1082
[2] Reactive and Functional Polymers, 2010, vol. 70, # 7, p. 400 - 407
[3] Patent: WO2014/194242, 2014, A2,
[4] Patent: WO2015/164374, 2015, A1,
  • 5
  • [ 7107-58-6 ]
  • [ 16801-63-1 ]
Reference: [1] Journal of Organic Chemistry, 1968, vol. 33, # 8, p. 3182 - 3187
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