Home Cart 0 Sign in  

[ CAS No. 66405-41-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 66405-41-2
Chemical Structure| 66405-41-2
Structure of 66405-41-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 66405-41-2 ]

Related Doc. of [ 66405-41-2 ]

Alternatived Products of [ 66405-41-2 ]

Product Details of [ 66405-41-2 ]

CAS No. :66405-41-2 MDL No. :MFCD09031995
Formula : C9H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AEZHUDXZHNLVKG-UHFFFAOYSA-N
M.W : 170.21 Pubchem ID :21249113
Synonyms :

Calculated chemistry of [ 66405-41-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.75
TPSA : 43.37 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) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 0.48
Log Po/w (WLOGP) : 1.31
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.0
Solubility : 17.0 mg/ml ; 0.1 mol/l
Class : Very soluble
Log S (Ali) : -0.96
Solubility : 18.7 mg/ml ; 0.11 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.68
Solubility : 3.55 mg/ml ; 0.0208 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 66405-41-2 ]

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 [ 66405-41-2 ]

* 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 [ 66405-41-2 ]
  • Downstream synthetic route of [ 66405-41-2 ]

[ 66405-41-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 14199-15-6 ]
  • [ 66405-41-2 ]
YieldReaction ConditionsOperation in experiment
97.4% With hydrogen In o-xylene at 140℃; for 7 - 8 h; Example 2: Preparation of 4-(methoxycarbonvmethvPcvclohexanone A high pressure autoclave was charged with a mixture of methyl (4- hydroxyphenyl)acetate (50 g, 0.30 mol), palladium ( 5g) (10 percent) on carbon (50 percent wet) and O- xylene (250 mL). The reaction mixture was stirred under 110 to 115 psi of hydrogen pressure for 7 to 8 h at 1400C. The reaction was monitored by HPLC. The reaction mixture was then cooled to room temperature, and the catalyst was filtered off. Filtrate was concentrated under reduced pressure to get 4-(methoxycarbonylmethyl)cyclohexanone as light yellow to colorless oily liquid (48.7 g, 97.4 percent).(M++!) 171, ' HNMR (400 MHz, CDCl 3): ? 1.48 - 1.51 ( m, 2H), 2.1 1-2.07 (m, 2H), 2.4- 2.23 (m, 7H), 3.7 (s, 3H).
97.4% With hydrogen In o-xylene; water at 140℃; for 8 h; Autoclave Example 2
Preparation of 4-(methoxycarbonymethyl)cyclohexanone
A high pressure autoclave was charged with a mixture of methyl (4-hydroxyphenyl)acetate (50 g, 0.30 mol), palladium (5 g) (10percent) on carbon (50percent wet) and O-xylene (250 mL).
The reaction mixture was stirred under 110 to 115 psi of hydrogen pressure for 7 to 8 h at 140° C.
The reaction was monitored by HPLC.
The reaction mixture was then cooled to room temperature, and the catalyst was filtered off.
Filtrate was concentrated under reduced pressure to get 4-(methoxycarbonylmethyl)cyclohexanone as light yellow to colorless oily liquid (48.7 g, 97.4percent).
(M++1) 171, 1HNMR (400 MHz, CDCl3): δ 1.48-1.51 (m, 2H), 2.11-2.07 (m, 2H), 2.4-2.23 (m, 7H), 3.7 (s, 3H).
69% at 90℃; for 80 h; Inert atmosphere; Large scale A 20 L reaction vessel was vacuum purged of air and flushed (6 ×)with N2. To this vessel blanketed in N2, 10percent Pd/C (300.0 g) wascarefully added followed by methyl 4-hydroxyphenylacetate (24;3.0 kg, 18.05 mol) at all times maintaining a slight positive pressure of N2 gas. AcOH (6.0 L) was then slowly added via a large additionfunnel. The resulting mixture was stirred and sparged with more N2(large bubbler) for some time. The N2 gas was then replaced with H2and the sparging continued as the reaction mixture was heated to 90 °C with continued H2 sparging for 80 h. At this time, the reactionmixture was cooled down to r.t. and the reaction vessel vacuumpurged (6 ×) with N2 gas. The heterogeneous solution was removedvia a tygon tube and carefully filtered through Celite and washedwith CH2Cl2 (4 L) at all times keeping the filter cake moist. The resultingsolution was concentrated in vacuo to provide a viscous liquid.The viscous liquid was purified by distillation (100 °C/0.5 mmHg) to provide 25 as a colorless oil; yield: 2.11 kg (69percent).1H NMR (500 MHz, CDCl3): δ = 3.69 (s, 3 H), 2.38 (m, 4 H), 2.33(m, 2 H), 2.27 (m, 1 H), 2.09 (m, 2 H), 1.47 (m, 2 H).MS (ESI+): m/z = 171.1 (M + 1).Anal. Calcd for C9H14O3: C, 63.51; H, 8.29. Found: C, 63.16; H,8.51
Reference: [1] Patent: WO2007/138435, 2007, A2, . Location in patent: Page/Page column 6
[2] Patent: US2011/124886, 2011, A1, . Location in patent: Page/Page column 3
[3] Angewandte Chemie - International Edition, 1998, vol. 37, # 4, p. 484 - 489
[4] Synthesis (Germany), 2014, vol. 46, # 22, p. 3047 - 3058
[5] Tetrahedron, 2014, vol. 70, # 30, p. 4563 - 4570
[6] Patent: WO2014/140241, 2014, A1, . Location in patent: Page/Page column 25
  • 2
  • [ 317338-46-8 ]
  • [ 66405-41-2 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In water; acetone at 20℃; for 15 h; A 1 N aqueous hydrochloric acid solution (50 mL)/acetone (200 ml) mixture of (1,4-dioxa-spiro[4.5]dec-8-yl)-acetic acid methyl ester (4.99 g) obtained in Example (1b) was stirred at room temperature for 15 hours. The organic solvent was removed using an evaporator. The remaining aqueous solution was subjected to two extractions with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated to obtain the title compound (4.30 g, quantitative yield) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ (ppm) = 3.71 (3H, s), 2.41-2.24 (7H, m), 2.12-2.05 (2H, m), 1.54-1.43 (2H, m); MS (EI) m/z: 170 (M)+.
100% With hydrogenchloride In water; acetone at 20℃; for 15 h; (1c)
(4-oxo-cyclohexyl)-acetic acid methyl ester
A 1 N aqueous hydrochloric acid solution (50 mL)/acetone (200 ml) mixture of the compound (4.99 g) obtained in Example (1b) was stirred at room temperature for 15 hours.
The organic solvent was removed using an evaporator.
The remaining aqueous solution was subjected to two extractions with ethyl acetate.
The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated to obtain the title compound (4.30 g, quantitative yield) as a colorless oil.
1H NMR (400 MHz, CDCl3) δ (ppm) = 3.71 (3H, s), 2.41-2.24 (7H, m), 2.12-2.05 (2H, m), 1.54-1.43 (2H, m);
MS (EI) m/z: 170 (M)+.
54% With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; Methyl 2-(4-(1,3-dioxalane)cyclohexyl)acetate (51.1 g, 238 mmol, 1.0 eq) was dissolved in THF (2 L). This was cooled to 0° C. and 2 N HCl (1.4 L, 2.8 mol, 12.0 eq) was added dropwise in 2.5 hours keeping T=0° C. The reaction mixture was stirred over night allowing it to warm to room temperature. Then water (1 L) and EtOAc (1 L) were added and the layers were separated. The aqueous layer was extracted with EtOAc (1 L). The combined organic layers were washed with brine (1 L) and dried (Na2SO4). The mixture was evaporated and purified by column chromatography (silica: EtOAc/heptane=1/4). Yield: 21.9 g, 54percent (clear oil) of methyl 2-(4-oxocyclohexyl)acetate. 1H NMR (CDCl3, 300 MHz) δ 1.50 (m, 2H), 2.16 (m, 2H), 2.36 (d, 2H), 2.38 (m, 1H), 2.39 (m, 4H), 3.71 (s, 3H)
Reference: [1] Patent: EP2256105, 2010, A1, . Location in patent: Page/Page column 25; 26
[2] Patent: EP2471777, 2012, A1, . Location in patent: Page/Page column 10
[3] Patent: US2009/36425, 2009, A1, . Location in patent: Page/Page column 18
  • 3
  • [ 91158-10-0 ]
  • [ 66405-41-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 8, p. 2496 - 2511
[2] Tetrahedron Letters, 1987, vol. 28, # 29, p. 3373 - 3376
  • 4
  • [ 172270-85-8 ]
  • [ 66405-41-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 38, p. 11599 - 11603[2] Angew. Chem., 2017, vol. 129, p. 11757 - 11761,5
[3] Patent: EP2471777, 2012, A1,
  • 5
  • [ 99183-13-8 ]
  • [ 66405-41-2 ]
YieldReaction ConditionsOperation in experiment
97 g at -10 - 25℃; for 2 h; To a cooled (∼10°C) solution of 100.3g (582.0mmol) of the above alcohol in 361mL of AcOH was added drop wise 954mL of a 5percent solution of NaOCl while maintaining the internal temperature EtOAc and the layers were separated. The aqueous layer was back extracted with EtOAc (3×500mL). The combined organic extracts were washed with 500mL of 20percent K2CO3 and then with 500mL of satd NaHCO3. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 97.0g (98percent) of 11, which was sufficiently pure for use in the next step.
Reference: [1] Tetrahedron, 2014, vol. 70, # 30, p. 4563 - 4570
  • 6
  • [ 637-88-7 ]
  • [ 66405-41-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 8, p. 2496 - 2511
[2] Tetrahedron Letters, 1987, vol. 28, # 29, p. 3373 - 3376
  • 7
  • [ 4746-97-8 ]
  • [ 66405-41-2 ]
Reference: [1] Patent: EP2471777, 2012, A1,
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 38, p. 11599 - 11603[3] Angew. Chem., 2017, vol. 129, p. 11757 - 11761,5
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 66405-41-2 ]

Aliphatic Cyclic Hydrocarbons

Chemical Structure| 10407-33-7

[ 10407-33-7 ]

Methyl 3-(2-oxocyclohexyl)propanoate

Similarity: 0.96

Chemical Structure| 13672-64-5

[ 13672-64-5 ]

Methyl 2-(2-oxocyclohexyl)acetate

Similarity: 0.96

Chemical Structure| 78478-61-2

[ 78478-61-2 ]

Methyl 5-oxobicyclo[2.2.2]octane-2-carboxylate

Similarity: 0.93

Chemical Structure| 62617-92-9

[ 62617-92-9 ]

Methyl 3-methyl-4-oxocyclohexanecarboxylate

Similarity: 0.93

Chemical Structure| 87122-06-3

[ 87122-06-3 ]

Dimethyl 5-oxocyclohexane-1,3-dicarboxylate

Similarity: 0.93

Esters

Chemical Structure| 10407-33-7

[ 10407-33-7 ]

Methyl 3-(2-oxocyclohexyl)propanoate

Similarity: 0.96

Chemical Structure| 13672-64-5

[ 13672-64-5 ]

Methyl 2-(2-oxocyclohexyl)acetate

Similarity: 0.96

Chemical Structure| 78478-61-2

[ 78478-61-2 ]

Methyl 5-oxobicyclo[2.2.2]octane-2-carboxylate

Similarity: 0.93

Chemical Structure| 62617-92-9

[ 62617-92-9 ]

Methyl 3-methyl-4-oxocyclohexanecarboxylate

Similarity: 0.93

Chemical Structure| 87122-06-3

[ 87122-06-3 ]

Dimethyl 5-oxocyclohexane-1,3-dicarboxylate

Similarity: 0.93

Ketones

Chemical Structure| 10407-33-7

[ 10407-33-7 ]

Methyl 3-(2-oxocyclohexyl)propanoate

Similarity: 0.96

Chemical Structure| 13672-64-5

[ 13672-64-5 ]

Methyl 2-(2-oxocyclohexyl)acetate

Similarity: 0.96

Chemical Structure| 120077-76-1

[ 120077-76-1 ]

Methyl 4-acetylcyclohexanecarboxylate

Similarity: 0.93

Chemical Structure| 62617-92-9

[ 62617-92-9 ]

Methyl 3-methyl-4-oxocyclohexanecarboxylate

Similarity: 0.93

Chemical Structure| 87122-06-3

[ 87122-06-3 ]

Dimethyl 5-oxocyclohexane-1,3-dicarboxylate

Similarity: 0.93