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[ CAS No. 94594-90-8 ] {[proInfo.proName]}

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Chemical Structure| 94594-90-8
Chemical Structure| 94594-90-8
Structure of 94594-90-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 94594-90-8 ]

CAS No. :94594-90-8 MDL No. :MFCD00066271
Formula : C10H17NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 215.31 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 94594-90-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.0
TPSA : 54.55 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 1.2
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.54 mg/ml ; 0.00716 mol/l
Class : Soluble
Log S (Ali) : -2.29
Solubility : 1.09 mg/ml ; 0.00507 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.927 mg/ml ; 0.00431 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.84

Safety of [ 94594-90-8 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 94594-90-8 ]

* 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 [ 94594-90-8 ]
  • Downstream synthetic route of [ 94594-90-8 ]

[ 94594-90-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 213914-68-2 ]
  • [ 213914-70-6 ]
  • [ 94594-90-8 ]
  • [ 60886-80-8 ]
YieldReaction ConditionsOperation in experiment
28.7%
Stage #1: With potassium hydroxide; dihydrogen peroxide In n-heptane; diethylene glycol dimethyl ether; water at 17℃; for 11 h;
Stage #2: With hydrogenchloride; sodium sulfite In diethylene glycol dimethyl ether; water at 5 - 21℃; for 1.58333 h;
In a round-bottomed flask, 40.00 g (0.105 mol) of (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide and 160 ml of diglyme were placed, and the mixture was cooled to 17° C. while nitrogen was being sent thereto with the intention of limiting the concentration of oxygen to 5percent or less until the end of the reaction. After 0.51 g (0.005 mol) of 35percent hydrogen peroxide solution was inpoured, 15.79 g (0.162 mol) of 35percent aqueous hydrogen peroxide solution and 19.61 g (0.168 mol) of 48percent aqueous potassium hydroxide solution were simultaneously inpoured at 17° C. over 9 hours, followed by stirring at 17° C. for 2 hours, and the end of the reaction was checked by HPLC.Separately, 21.14 g (0.168 mol) of sodium sulfite was dissolved in 110 ml of water in a flask with a stop-cock at room temperature, 58.97 g (0.566 mol) of 35percent hydrochloric acid was added dropwise at 9 to 10° C., and then the above-mentioned reaction mixture was added dropwise thereto at 5 to 12° C. over 1 hour. After the resultant mixture was heated to 21° C. and stirred at the same temperature for 35 min, 200 ml of methyl tert-butyl ether was inpoured thereto, the mixture was stirred for 10 min, and the water layer was removed by separation. The organic layer was washed with saline solution (1.60 g NaCl, 200 ml tap water), 2.40 g of n-heptane and saline solution (1.60 g NaCl, 200 ml tap water) were added thereto, the mixture was stirred for 15 min, the water layer was removed by separation, and the end of washing was checked by GC. The organic layer was concentrated at normal pressures, and 240 ml of n-heptane was added to the obtained residue, which was then vacuum-concentrated until the residue was reduced to about 160 ml. Then, the residue was cooled and stirred at 0 to 10° C. for 30 minutes. The obtained crystal was filtered, washed with 40 ml of n-heptane, and dried under reduced pressure. Thus, 6.48 g of camphorsultam (yield based on (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide: 28.7percent; GC area percentage value: 98.23percent) was obtained. (1S)-2,10-camphorsulfonimine (imine form) was contained in the recovered camphorsultam and couldn't be removed by purification.Meanwhile, the filtrate was concentrated under reduced pressure and n-heptane was added thereto, to obtain 72.17 g (corresponding to 0.105 mol) of (2S)-2-(2-propenyl) octanoic acid/heptane solution. From this of which amount was corresponding to 0.087 mol, cyclohexylamine salt of (2S)-2-(2-propenyl) octanoic acid was derived.In a round-bottomed flask, 241 ml of ethyl acetate, 7.78 g (0.078 mol) of cyclohexylamine were placed and 9.00 g (0.013 mol) of (2S)-2-(2-propenyl) octanoic acid/heptane solution was added dropwise thereto at 20° C. over a 30 minute period, followed by stirring at 20 to 21° C. for 1 hour. Further, 51.00 g (corresponding to 0.074 mol) of (2S)-2-(2-propenyl) octanoic acid/heptane solution was added dropwise thereto at 20° C. over 2 hour 30 min. Then, the mixture was cooled and kept within the range of -3 to 3° C. for 1 hour. The crystal was collected by filtration, washed with 64 ml of cooled ethyl acetate, and dried under reduced pressure. Thus, 20.29 g of cyclohexylamine salt of (2S)-2-(2-propenyl) octanoic acid (yield based on (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide: 82.1percent; optical purity: 100percent) was obtained.
Reference: [1] Patent: US2009/118542, 2009, A1, . Location in patent: Page/Page column 6
  • 2
  • [ 94594-90-8 ]
  • [ 60933-63-3 ]
  • [ 60886-80-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 2, p. 423 - 428
  • 3
  • [ 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
  • 4
  • [ 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
  • 5
  • [ 80-62-6 ]
  • [ 94594-90-8 ]
  • [ 116195-15-4 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 6, p. 3941 - 3953
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