Home Cart 0 Sign in  
X

[ CAS No. 108354-78-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 108354-78-5
Chemical Structure| 108354-78-5
Chemical Structure| 108354-78-5
Structure of 108354-78-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 108354-78-5 ]

Related Doc. of [ 108354-78-5 ]

Alternatived Products of [ 108354-78-5 ]

Product Details of [ 108354-78-5 ]

CAS No. :108354-78-5 MDL No. :MFCD00130099
Formula : C10H13NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :DKYYKIHEIOOWRB-UHFFFAOYSA-N
M.W : 211.28 Pubchem ID :2756552
Synonyms :

Calculated chemistry of [ 108354-78-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.43
TPSA : 80.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 2.89
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 3.09
Consensus Log Po/w : 2.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.167 mg/ml ; 0.000789 mol/l
Class : Soluble
Log S (Ali) : -4.24
Solubility : 0.0121 mg/ml ; 0.0000573 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.5
Solubility : 0.668 mg/ml ; 0.00316 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.83

Safety of [ 108354-78-5 ]

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 [ 108354-78-5 ]

* 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 [ 108354-78-5 ]
  • Downstream synthetic route of [ 108354-78-5 ]

[ 108354-78-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 108-94-1 ]
  • [ 105-34-0 ]
  • [ 108354-78-5 ]
YieldReaction ConditionsOperation in experiment
82% With morpholine; sulfur In ethanol for 3 h; Reflux Synthesis of compounds 1, 2a-i and 3a-i
Compound 1 was prepared through standard Gewald reaction.
14
4.4 g (0.05 mol) of morpholine was added dropwise into a stirred solution of cyclohexanone (4.91 g, 0.05 mol), methyl cyanoacetate (4.95 g, 0.05 mol) and sulfur (1.92 g, 0.06 mol) in 35 mL ethanol.
On completion, the mixture was refluxed for further 3 h.
After cooling to room temperature, the precipitate was separated by filtration and recrystallized from ethanol to give 1 as pale yellow powders (8.6 g, 82percent yield), mp 128.2-129.4 °C (lit.
15
128-130 °C), MS (GC-MS): m/z, 211 [M+H]+, 179, 151, 125, 91, 77, 65, 53.
70% With sulfur; triethylamine In ethanol at 20℃; Inert atmosphere To EtOH (37.5 mL) in an open flask was added S8 (4.68 g, 150 mmol, 1.0 eq.),cyclohexanone (23.3 mL, 225 mmol, 1.5 eq.), methyl cyanoacetate (13.3. mL, 150 mmol,1.0 eq.), and Et3N (10.4 mL, 75 mmol, 0.5 eq.), and the reaction was stirred at rt overnight.The flask was cooled to 0 °C with no stirring for 5 h followed by collection of theprecipitate by filtration. The solid was washed with ice cold EtOH then dried at rt overnight to yield 6a asan off-white solid (22.1 g, 105 mmol, 70percent)
20%
Stage #1: With diethylamine In ethanol for 0.166667 h; Reflux
Stage #2: With sulfur In ethanol for 3 h; Reflux
EXAMPLE 11; The reaction scheme for the synthesis of azo dye 11 is shown below. In a Gewald reaction, diethylamine (8 ml) was added to a solution of equimolar quantities of cyclohexanone (9.80 g, 0.10 mol) and methyl cyanoacetate (9.90 g, 0.10 mol) in ethanol, and the mixture was refluxed for 10 minutes. Then sulfur (3.53 g, 0.11 mol) was added, and the solution was refluxed for a further 3 hours. The pale yellow precipitate that formed was filtered and washed with cooled ethanol to give 11a as a pale yellow powder (4.22 g, 20percent yield), m.p. 132-133° C.
Reference: [1] Asian Journal of Chemistry, 2010, vol. 22, # 9, p. 7399 - 7404
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 12, p. 1942 - 1956
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 8, p. 1866 - 1871
[4] Tetrahedron, 2006, vol. 62, # 29, p. 7121 - 7131
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1947 - 1953
[6] Chemical Biology and Drug Design, 2010, vol. 76, # 2, p. 116 - 129
[7] ChemMedChem, 2015, vol. 10, # 1, p. 69 - 82
[8] Patent: US2010/81823, 2010, A1, . Location in patent: Page/Page column 8
[9] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 305 - 308
[10] Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3620 - 3635
[11] Transition Metal Chemistry, 2014, vol. 39, # 4, p. 431 - 442
[12] Synlett, 2014, vol. 25, # 9,
[13] Journal of Molecular Liquids, 2017, vol. 243, p. 85 - 90
[14] Patent: WO2003/101979, 2003, A1, . Location in patent: Page 19
[15] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 239 - 251
  • 2
  • [ 108-94-1 ]
  • [ 105-56-6 ]
  • [ 108354-78-5 ]
YieldReaction ConditionsOperation in experiment
75% With sulfur; diethylamine In ethanol at 45 - 50℃; for 1 h; Intermediate 1. To a suspension of sulfur (11.5 g, 359 mmol) and ethyl 2- cyanoacetate (38.7 g, 342 mmol) in 50 mL of ethanol was added cyclohexan-l-one (33.6 g, 342 mmol) drop-wise at room temperature, followed by addition of diethyl amine (DEA) (25.0 g, 342 mmol), making sure the temperature was maintained below 50 °C. The resulting mixture was stirred at 45 °C for 1 h, before being cooled to 0 °C and filtered. The collected material was washed with cold ethanol and dried under vacuum to give Intermediate 1 as yellow solid (57.8 g, yield: 75percent).
Reference: [1] Patent: WO2012/12712, 2012, A2, . Location in patent: Page/Page column 47-48
  • 3
  • [ 10544-50-0 ]
  • [ 108-94-1 ]
  • [ 105-34-0 ]
  • [ 108354-78-5 ]
Reference: [1] Synlett, 2014, vol. 25, # 20, p. 2918 - 2922
  • 4
  • [ 67-56-1 ]
  • [ 108-94-1 ]
  • [ 372-09-8 ]
  • [ 108354-78-5 ]
Reference: [1] Journal of Chemical Research, 2004, # 5, p. 360 - 361
  • 5
  • [ 67-56-1 ]
  • [ 4506-71-2 ]
  • [ 108354-78-5 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 3, p. 1018 - 1021
  • 6
  • [ 108354-78-5 ]
  • [ 1240361-06-1 ]
Reference: [1] Chemical Biology and Drug Design, 2010, vol. 76, # 2, p. 116 - 129
[2] Chemical Biology and Drug Design, 2010, vol. 76, # 2, p. 130 - 141
Recommend Products
Same Skeleton Products
Historical Records