Home Cart 0 Sign in  

[ CAS No. 676560-15-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 676560-15-9
Chemical Structure| 676560-15-9
Structure of 676560-15-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 676560-15-9 ]

Related Doc. of [ 676560-15-9 ]

Alternatived Products of [ 676560-15-9 ]

Product Details of [ 676560-15-9 ]

CAS No. :676560-15-9 MDL No. :MFCD24038913
Formula : C15H30O3Si Boiling Point : -
Linear Structure Formula :- InChI Key :VFEJEBVELPDVHI-UHFFFAOYSA-N
M.W : 286.48 Pubchem ID :23144129
Synonyms :

Calculated chemistry of [ 676560-15-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.93
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 82.34
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.97
Log Po/w (XLOGP3) : 4.35
Log Po/w (WLOGP) : 4.13
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 1.91
Consensus Log Po/w : 3.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.96
Solubility : 0.0314 mg/ml ; 0.000109 mol/l
Class : Soluble
Log S (Ali) : -4.81
Solubility : 0.00442 mg/ml ; 0.0000154 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.116 mg/ml ; 0.000406 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.69

Safety of [ 676560-15-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 676560-15-9 ]

* 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 [ 676560-15-9 ]
  • Downstream synthetic route of [ 676560-15-9 ]

[ 676560-15-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 3618-04-0 ]
  • [ 18162-48-6 ]
  • [ 676560-15-9 ]
YieldReaction ConditionsOperation in experiment
100% With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 35℃; for 12 h; A. 4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester. To a solution of tert-butyldimethylsilyl chloride (10.6 g, 70 mmol) and imidazole (9.9 g, 145 mmol) in DMF (20 mL) was added 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (9.4 mL, 58 mmol). The mixture was stirred at 35° C. for 12 h, diluted with EtOAc (100 mL), washed with H2O (3.x.), dried (Na2SO4), and concentrated. The resulting white solid was isolated in quantitative yield (16.6 g) and was used in the next step without purification.
96% With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3 h; Example 3 : 8-(3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-lH-pyrazol-l-yl)-2- oxaspiro [4.5] decan-1-one; Step 1: ethyl 4-(tert-butyldimethyIsilyloxy)cyclohexanecarboxylate.; [124] tert-Butyldimethylsilyl chloride (3.61 g, 0.0240 mol) was added to a solution of 4- hydroxy-cyclohexanecarboxylic acid ethyl ester (3.44 g, 0.0200 mol; ), and lH-imidazole (3.40 g, 0.0499 mol; ) in N,N-Dimethylformamide (5.0 mL, 0.064 mol). The mixture was stirred at the room temperature for 3 hours. The mixture was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with brine, dried over sodium sulfate, filtered, and then concentrated to give oily crude product. Column chromatography eluting with 0-20percent ethyl acetate/hexanes gave 5.5 g (96percent) of the title compound as colorless oil. 1H-NMR (300 MHz, CD3Cl) δ 4.12 (m, 2H), 3.72 (m, IH), 2.29 (m, IH), 1.93 (m, 2H), 1.65 (m, 2H), 1.56 (m, 2H), 1.48 (m, 2H), .125 (m, 3H), 0.88 (d, 6H), 0.03 (d, 6H).
45%
Stage #1: With triethylamine In dichloromethane at 20℃; for 0.333333 h;
Stage #2: at 20℃; for 40 h;
To a solution of ethyl 4-hydroxycyclohexane-1-carboxylate (10 g, 58.06 mmol) in dichloromethane (25 mL) was added triethylamine (13 g, 128.47 mmol) slowly at room temperature. After stirring for additional 20 min, TBDMSC1 (24.9 g, 87.09 mmol) was slowly added. The resulting reaction mixture was then stirred at room temperature for 40 h. The reaction mixture was quenched by the addition of water (100 mL) and extracted with dichloromethane (100 mL×2). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (1percent to 10percent gradient) to yield ethyl 4-[(tert-butyldimethylsilyl)oxy]cyclohexane-1-carboxylate as yellow oil (7.5 g, 45percent).
79% With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 18 h; EXAMPLE 5
5-Butyl-9-[1-(4,6-dimethyl-pyrimidine-5-carbonyl)-4-methyl-piperidin-4-yl]-3-(trans-4-hydroxy-cyclohexylmethyl)-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one (I-4)
4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38)-To a solution of 4-oxy-cyclohexanecarboxylic acid ethyl ester (CASRN 17159-80-7, 1.7 g, 0.01 mol) in DMF (14 mL) was added DMAP (58 mg, 0.47 mmol), TEA (1.54 mL) and tert-butyl-dimethylsilyl chloride (1.65 g, 0.011 mol).
The reaction mixture was stirred at RT for 18 h, poured into ice (10 g), extracted with EtOAc (3*50 mL).
The organic extracts were dried (MgSO4) filtered and concentrated.
The residue was purified by SiO2 chromatography eluding with EtOAc/hexane (1:20) to afford 2.25 g (79percent) of 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38) as colorless oil.
34.94 g With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15 h; Cooling with ice Compound 5 (20.04 g) and imidazole (15.84 g) were dissolved in N,N-dimethylformamide (116 mL), tert-butyldimethylsilylchloride (19.47 g) was added under ice cooling, and the mixture was stirred at room temperature for 15hours. The reaction solution was added to ice water, and the mixture was extracted with diethyl ether. The extract waswashed with water and saturated brine. The solution was dried over anhydrous magnesium sulfate, and concentratedunder reduced pressure to obtain Compound 6 (34.94 g) as a colorless oil.MS (m/z): 287 [M+H]+
43.1 g With 1H-imidazole In N,N-dimethyl-formamide at 20℃; tert-Butyldimethylsilyl chloride (26.3 g, hydroxycyclohexanecarboxylate (25.0 g, 171 59-80-7) and imidazole (24.7 g, 363174 mmol) was added to a solution of ethyl 4-145 mmol, mixture of cis-/trans-isomers, Gas Nommol) in N,N-dimethylformamide (36 ml) and the mixture was stirred over night at room temperature. For work-up, water was added and the mixture was extracted with tert-butyl methyl ether (3x). The combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressure to yield ethyl 4-[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (43.1 g, 104percent yield) which was used in the next step without further purification. 1HNMR (400 MHz, DMSO-d6, mixture of isomers): 6 [ppm] = 4.10-3.99 (m, 2H), 3.93-3.86 (m, 0.7H), 3.63-3.51 (m, 0.3H), 2.39-2.28 (m, 0.8H), 2.27-2.14 (m, 0.3H), 1.91-1.21 (m, 8H), 1.20-1.13 (m, 3H), 0.89-0.79 (m, 9H), 0.08-0.00 (m, 6H).

Reference: [1] Patent: US2006/4039, 2006, A1, . Location in patent: Page/Page column 13
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 2, p. 129 - 134
[3] Patent: WO2009/9059, 2009, A1, . Location in patent: Page/Page column 30
[4] Journal of Organic Chemistry, 1994, vol. 59, # 10, p. 2748 - 2761
[5] Patent: US2016/75711, 2016, A1, . Location in patent: Paragraph 0219-0220
[6] Patent: US2008/249087, 2008, A1, . Location in patent: Page/Page column 24-25
[7] Patent: WO2009/24821, 2009, A2, . Location in patent: Page/Page column 81
[8] Patent: WO2009/37294, 2009, A1, . Location in patent: Page/Page column 64-65
[9] Patent: WO2007/76086, 2007, A2, . Location in patent: Page/Page column 54-55
[10] Patent: WO2004/26822, 2004, A2, . Location in patent: Page 68
[11] Patent: EP2862856, 2015, A1, . Location in patent: Paragraph 0693; 0694
[12] Tetrahedron, 2016, vol. 72, # 27-28, p. 4032 - 4038
[13] Patent: WO2016/177658, 2016, A1, . Location in patent: Page/Page column 223; 224
[14] Patent: WO2018/78005, 2018, A1, . Location in patent: Page/Page column 115
[15] Patent: WO2018/78009, 2018, A1, . Location in patent: Page/Page column 118; 119
[16] Patent: WO2007/107565, 2007, A1, . Location in patent: Page/Page column 72-73
[17] Patent: WO2008/119713, 2008, A1, . Location in patent: Page/Page column 58
[18] Patent: WO2008/101914, 2008, A2, . Location in patent: Page/Page column 65
[19] Patent: WO2007/107566, 2007, A1, . Location in patent: Page/Page column 73-74
[20] Patent: WO2007/107567, 2007, A1, . Location in patent: Page/Page column 54; 59
  • 2
  • [ 3618-04-0 ]
  • [ 69739-34-0 ]
  • [ 676560-15-9 ]
Reference: [1] Amino Acids, 2013, vol. 45, # 5, p. 1157 - 1168
  • 3
  • [ 288-32-4 ]
  • [ 3618-04-0 ]
  • [ 18162-48-6 ]
  • [ 676560-15-9 ]
Reference: [1] Patent: US2004/259843, 2004, A1,
[2] Patent: US2005/215784, 2005, A1,
  • 4
  • [ 108-48-5 ]
  • [ 3618-04-0 ]
  • [ 676560-15-9 ]
Reference: [1] Patent: EP3418282, 2018, A1,
Same Skeleton Products
Historical Records