Home Cart 0 Sign in  

[ CAS No. 1221819-46-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1221819-46-0
Chemical Structure| 1221819-46-0
Structure of 1221819-46-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1221819-46-0 ]

Related Doc. of [ 1221819-46-0 ]

Alternatived Products of [ 1221819-46-0 ]

Product Details of [ 1221819-46-0 ]

CAS No. :1221819-46-0 MDL No. :MFCD16652327
Formula : C10H10O3S Boiling Point : -
Linear Structure Formula :- InChI Key :NCHCTLRZIXTLPI-UHFFFAOYSA-N
M.W : 210.25 Pubchem ID :46203852
Synonyms :

Calculated chemistry of [ 1221819-46-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.45
TPSA : 51.75 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) : -7.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 0.36
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.56
Solubility : 5.85 mg/ml ; 0.0278 mol/l
Class : Very soluble
Log S (Ali) : -1.01
Solubility : 20.5 mg/ml ; 0.0974 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.93
Solubility : 0.248 mg/ml ; 0.00118 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.66

Safety of [ 1221819-46-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1221819-46-0 ]

* 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 [ 1221819-46-0 ]
  • Downstream synthetic route of [ 1221819-46-0 ]

[ 1221819-46-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 6704-31-0 ]
  • [ 3112-85-4 ]
  • [ 1221819-46-0 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.666667 h;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran; hexane for 0.5 h;
Stage #3: at -78℃; for 2 h;
To a solution of (methylsulfonyl)benzene (2.2 g, 13.9 mmol) in THF (38 mL) at 0 was added n-BuLi (2.5 M in hexanes, 12.2 mL, 30.6 mmol) dropwise over 10 minutes. After the mixture was stirred for 30 min, chlorodiethylphosphonate (2.4 mL, 16.7 mmol) was added dropwise to the reaction. After 30 minutes, a solution of oxetan-3-one (1.0 g, 13.9 mmol) in THF (2 mL) was added dropwise to the reaction mixture at -78 . The reaction mixture was stirred at -78 for 2 hours, then diluted with aqueous NH4Cl (100 mL) and extracted with EtOAc (100 mL x 2) . The combined organic layers were concentrated and the residue was purified by silica gel chromatxography column (petroleum ether/EtOAc = 3/1) to give the title compound (2.4 g, 82percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) : δ7.90-7.88 (m, 2H) , 7.68-7.64 (m, 1H) , 7.57 (t, J= 7.6 Hz, 2H) , 6.13-6.11 (m, 1H) , 5.66-5.64 (m, 2H) , 5.30-5.27 (m, 2H).
75%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.75 h; Inert atmosphere
Stage #2: With diethyl chlorophosphate In tetrahydrofuran; hexane at 0℃; for 0.5 h;
Stage #3: at -78℃; for 2 h;
3-((Phenylsulfonyl)methylene)oxetane
To an oven-dried vial was added (methylsulfonyl)benzene (0.570 g, 3.65 mmol) and the vial was evacuated with argon 3 times.
The dry THF (17 mL) was added and the reaction was cooled to 0° C. The 2.5 M BuLi in hexanes (3.21 mL, 8.03 mmol) was added dropwise and the reaction began to stir at 0° C. and stirred for 45 minutes.
The diethyl chlorophosphate (0.528 mL, 3.65 mmol) was then added at 0° C. and the reaction stirred for 30 minutes.
The reaction was then cooled to -78° C. and the oxetan-3-one (0.330 mL, 5.15 mmol) was then added dropwise and the reaction stirred for 2 h.
The reaction was then warmed to rt and filtered through a silica plug.
The reaction was then concentrated onto silica and purified by MPLC (20 min, 0-40percent EtOAc:hex) to provide pure 3-((phenylsulfonyl)methylene)oxetane (0.579 g, 2.75 mmol, 75percent yield).
1H NMR (400 MHz, CDCl3): δ 7.91-7.87 (m, 2H), 7.69-7.64 (m, 1H), 7.60-7.55 (m, 2H), 6.12 (quintet, J=2.3 Hz, 1H), 5.66-5.63 (m, 2H), 5.30-5.27 (m, 2H).
Reference: [1] Patent: WO2018/137619, 2018, A1, . Location in patent: Page/Page column 54; 55
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3227 - 3246
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8540 - 8562
[4] Patent: US2015/238473, 2015, A1, . Location in patent: Paragraph 0271
[5] Patent: WO2013/16197, 2013, A1, . Location in patent: Page/Page column 92
[6] Patent: WO2013/188856, 2013, A1, . Location in patent: Paragraph 0275
  • 2
  • [ 6704-31-0 ]
  • [ 56069-39-7 ]
  • [ 1221819-46-0 ]
Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 31, p. 4530 - 4542
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1221819-46-0 ]

Aryls

Chemical Structure| 22821-77-8

[ 22821-77-8 ]

4-(Methylsulfonyl)benzyl Alcohol

Similarity: 0.79

Chemical Structure| 220798-39-0

[ 220798-39-0 ]

(3-(Methylsulfonyl)phenyl)methanol

Similarity: 0.79

Chemical Structure| 5535-48-8

[ 5535-48-8 ]

(Vinylsulfonyl)benzene

Similarity: 0.77

Chemical Structure| 127-63-9

[ 127-63-9 ]

Sulfonyldibenzene

Similarity: 0.76

Chemical Structure| 14763-60-1

[ 14763-60-1 ]

4-(Methylsulfonyl)phenol

Similarity: 0.76

Alkenes

Chemical Structure| 5535-48-8

[ 5535-48-8 ]

(Vinylsulfonyl)benzene

Similarity: 0.77

Chemical Structure| 97042-18-7

[ 97042-18-7 ]

4-((4-(Allyloxy)phenyl)sulfonyl)phenol

Similarity: 0.75

Chemical Structure| 1424-51-7

[ 1424-51-7 ]

3-(Phenylsulfonyl)acrylonitrile

Similarity: 0.71

Chemical Structure| 95535-40-3

[ 95535-40-3 ]

4-(Vinylsulfonyl)benzoic acid

Similarity: 0.69

Chemical Structure| 179174-79-9

[ 179174-79-9 ]

(Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acid

Similarity: 0.64

Sulfones

Chemical Structure| 22821-77-8

[ 22821-77-8 ]

4-(Methylsulfonyl)benzyl Alcohol

Similarity: 0.79

Chemical Structure| 220798-39-0

[ 220798-39-0 ]

(3-(Methylsulfonyl)phenyl)methanol

Similarity: 0.79

Chemical Structure| 5535-48-8

[ 5535-48-8 ]

(Vinylsulfonyl)benzene

Similarity: 0.77

Chemical Structure| 127-63-9

[ 127-63-9 ]

Sulfonyldibenzene

Similarity: 0.76

Chemical Structure| 14763-60-1

[ 14763-60-1 ]

4-(Methylsulfonyl)phenol

Similarity: 0.76

Related Parent Nucleus of
[ 1221819-46-0 ]

Aliphatic Heterocycles

Chemical Structure| 1172500-91-2

[ 1172500-91-2 ]

4-Benzenesulfonylpiperidine Hydrochloride

Similarity: 0.56

Chemical Structure| 346688-38-8

[ 346688-38-8 ]

4-(3-(Methylsulfonyl)phenyl)-1-propylpiperidine

Similarity: 0.56

Chemical Structure| 916488-42-1

[ 916488-42-1 ]

1-(2-(Methylsulfonyl)phenyl)piperazine hydrochloride

Similarity: 0.50