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[ CAS No. 116195-15-4 ] {[proInfo.proName]}

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Chemical Structure| 116195-15-4
Chemical Structure| 116195-15-4
Structure of 116195-15-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 116195-15-4 ]

CAS No. :116195-15-4 MDL No. :MFCD30530177
Formula : C14H21NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :BALAVPVKVQRBKA-JTNHKYCSSA-N
M.W : 283.39 Pubchem ID :11098052
Synonyms :

Calculated chemistry of [ 116195-15-4 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.79
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 78.05
TPSA : 62.83 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) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.63
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : 1.61
Consensus Log Po/w : 1.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.274 mg/ml ; 0.000967 mol/l
Class : Soluble
Log S (Ali) : -3.42
Solubility : 0.107 mg/ml ; 0.000377 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.42
Solubility : 1.07 mg/ml ; 0.00378 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 5.01

Safety of [ 116195-15-4 ]

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 [ 116195-15-4 ]

* 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 [ 116195-15-4 ]
  • Downstream synthetic route of [ 116195-15-4 ]

[ 116195-15-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 94594-90-8 ]
  • [ 920-46-7 ]
  • [ 116195-15-4 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With sodium hydride In toluene for 1.5 h;
Stage #2: at 20℃;
Example 2(R)-5-Methyl-4,5-dihydro-pyrazole-1 ,5-dicarboxylic acid 1 -[(4-chloro-phenyl)-amide] 5-[2-fluoro-4- (2-oxo-2H-pyridin-1-yl)-phenyl]-amide}Step 1. Synthesis of (3aS,6R,7aR)-1-methacryloyl-8,8-dimethylhexahydro-3a,6-methano-2,1- benzisothiazole 2,2-dioxide(1 S)-(-)-2,10-camphorsultamProcedure: To a solution of (1S)-(-)-2,10-camphorsultam (1.160g, 5.388 mmoles) in toluene (10ml) was added sodium hydride (60percent in oil, 0.323g, 8.08 mmoles). Stirred for 1.5 hours Added methacryoyl chloride (1.126g, 10.78 mmoles) directly to the reaction mixture. Stirred at room temperature overnight, Evaporated, extracted into ethylacetate, washed with 1 N HCI, dried MgSO4, evaporated in vacuo and purified by chromatography (0-20percent EtOAc in hexane) to afford the desired compound (1.24Og, 81percent) 1 H NMR (400 MHz, DMSO-D6) δ ppm 0.90 (s, 3 H), 1.08 (s, 3 H), 1.23 (m 1 H), 1.42 (m, 1 H), 1.78 (m, 5 H), 1.81 (m, 3H), 3.26 (s, 4 H), 3.56 (d, J=14.04 Hz, 1 H), 3.77 (d, J=14.04 Hz, 1 H)1 3.91 (m, 1 H), 5.48 (s, 1 H)1 5.60 (s,1 H)
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3218 - 3227
[2] Patent: WO2008/65503, 2008, A1, . Location in patent: Page/Page column 36
[3] Tetrahedron Asymmetry, 1991, vol. 2, # 12, p. 1359 - 1370
  • 2
  • [ 760-93-0 ]
  • [ 94594-90-8 ]
  • [ 116195-15-4 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With triethylamine; lithium chloride In tetrahydrofuran at -20℃; for 0.166667 h;
Stage #2: at -20 - -10℃; for 0.0833333 h;
Example 3Step 1. Synthesis of (3aS,6R,7aR)-1 -methacιyloyl-8,8-dimethylhexahydro-3a,6-methano-2,1- benzisothiazole 2,2-dioxide.(1 S)-(-)-2,10-camphorsultamProcedure: To a solution of the (1S)-(-)-2,10-camphorsultam (5.00Og, 23.22 mmoles) in anhydrous THF (50ml) at -20° C was added lithium chloride (1.08g, 25.5 mmoles, - small balls), triethylamine (4.21 ml, 30.2 mmoles, 1.30 equivalents.) and then the mixture was allowed to stir for 10 minutes. The lithium chloride did not go into solution. 2-methylacrylic anhydride (4.15 ml, 27.9 mmoles, 1.20 equivalents.) in THF (15ml) was then added. The internal temperature varied between -20° C and -10° C during addition which took about 5 minutes. The thick white mixture was stirred within the cooling bath and allowed to reach room temperature. After stirring overnight the white heterogeneous reaction mixture was added to 350ml of water with stirring. The white crystalline solid (3aS,6R,7aR)-1 -methacryloyl-8,8- dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide (6.302g, 96percent yield) was collected and dried under vacuum.-Analytical HPLC run with a Vydac 218TP54 C18 reverse phase column run with solvents A: 0.1percent trifluoroacetic acid in H2O and B: 0.1percent trifluoroacetic acid in acetonitrile. Gradient (0 to 100percentB) over 22 minutes. Retention time 18.166 min (100percent).Optical rotation = 0.02Og in 2ml; c=0.01g/ml (C= 1 (CHCI3)}; measurement -0.226; optical rotation = - 0.226x4000/10 = - 90.4.Combustion Anal sis:Steps 2 through 5 were performed as in Example 2.
Reference: [1] Patent: WO2008/65503, 2008, A1, . Location in patent: Page/Page column 40
[2] Journal of Organic Chemistry, 1995, vol. 60, # 7, p. 2271 - 2273
  • 3
  • [ 80-62-6 ]
  • [ 94594-90-8 ]
  • [ 116195-15-4 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 6, p. 3941 - 3953
  • 4
  • [ 94594-91-9 ]
  • [ 116195-15-4 ]
Reference: [1] Tetrahedron Asymmetry, 1991, vol. 2, # 12, p. 1359 - 1370
[2] Tetrahedron Asymmetry, 1991, vol. 2, # 12, p. 1359 - 1370
  • 5
  • [ 133705-97-2 ]
  • [ 116195-15-4 ]
Reference: [1] Tetrahedron Asymmetry, 1991, vol. 2, # 12, p. 1359 - 1370
  • 6
  • [ 119897-85-7 ]
  • [ 116195-15-4 ]
Reference: [1] Tetrahedron Asymmetry, 1991, vol. 2, # 12, p. 1359 - 1370
  • 7
  • [ 119897-86-8 ]
  • [ 116195-15-4 ]
Reference: [1] Tetrahedron Asymmetry, 1991, vol. 2, # 12, p. 1359 - 1370
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