21806-61-1|Prop-1-ene-1,3-sultone| Ambeed

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Quality Control of [ 21806-61-1 ] Purity: 98% SDS Specification

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Product Details of [ 21806-61-1 ]

CAS No. :	21806-61-1
Formula :	C₃H₄O₃S
M.W :	120.13
SMILES Code :	O=S1(C=CCO1)=O
MDL No. :	MFCD12405143
InChI Key :	KLLQVNFCMHPYGL-UHFFFAOYSA-N
Pubchem ID :	10898703

Safety of [ 21806-61-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 21806-61-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	7
Num. arom. heavy atoms	0
Fraction Csp3	0.33
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	24.0
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	51.75 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.84
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.35
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.94
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.63
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.36
Solubility	51.9 mg/ml ; 0.432 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.27
Solubility	63.8 mg/ml ; 0.531 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.14
Solubility	167.0 mg/ml ; 1.39 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.28 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.2

Application In Synthesis of [ 21806-61-1 ]

* 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.

Downstream synthetic route of [ 21806-61-1 ]

[ 21806-61-1 ] Synthesis Path-Downstream 1~35

1
[ 21806-61-1 ]
[ 123-35-3 ]
(+/-)-5-(4'-methylpenta-3'-en-1'-yl)-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]
(+/-)-6-(4'-methylpenta-3'-en-1'-yl)-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]

References: [1]Chemical Communications,1997,p. 611 - 612.
[2]Tetrahedron,1999,vol. 55,p. 2245 - 2262.

2
[ 21806-61-1 ]
[ 2495-32-1 ]
(+/-)-5-t-butyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]
(+/-)-6-t-butyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]

References: [1]Chemical Communications,1997,p. 611 - 612.
[2]Tetrahedron,1999,vol. 55,p. 2245 - 2262.

3
[ 21806-61-1 ]
[ 542-92-7 ]
(+/-)-endo-4,3-oxathiatricyclo<5.2.1.0^2,6>deca-8-ene 3,3-dioxide [ No CAS ]
(+/-)-exo-4,3-oxathiatricyclo<5.2.1.0^2,6>deca-8-ene 3,3-dioxide [ No CAS ]

References: [1]Chemical Communications,1997,p. 611 - 612.
[2]Chemical Communications,1997,p. 611 - 612.
[3]Tetrahedron,1999,vol. 55,p. 2245 - 2262.
[4]Tetrahedron,1999,vol. 55,p. 2245 - 2262.

4
[ 21806-61-1 ]
[ 2207-27-4 ]
(+/-)-endo-10,10-dimethoxy-1,7,8,9-tetrachloro-4,3-oxathiatricyclo<5.2.1.0^2,6>deca-8-ene 3,3-dioxide [ No CAS ]

References: [1]Tetrahedron,1999,vol. 55,p. 2245 - 2262.
[2]Chemical Communications,1997,p. 611 - 612.

5
[ 21806-61-1 ]
[ 1165952-91-9 ]
(+/-)-endo-4,3-oxathiatricyclo<5.2.2.0^2,6>undeca-8-ene 3,3-dioxide [ No CAS ]

References: [1]Chemical Communications,1997,p. 611 - 612.
[2]Tetrahedron,1999,vol. 55,p. 2245 - 2262.
[3]Synthesis,2004,p. 1696 - 1712.

6
[ 21806-61-1 ]
[ 513-81-5 ]
(+/-)-5,6-dimethyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]

References: [1]Chemical Communications,1997,p. 611 - 612.
[2]Tetrahedron,1999,vol. 55,p. 2245 - 2262.

7
[ 189756-89-6 ]
[ 21806-61-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In toluene; for 3h;Product distribution / selectivity;	Preparation of (Z)-3-(tert-butylamino)prop-1-ene-1-sulfonic acid (Compound N20); To a boiling solution of allyl bromide (21.6 mL, 250 mmol) in a solvent mixture of EtOH and H2O (200 mL, v/v=3:1) was added dropwise a solution of sodium sulfite (15.75 g, 125 mmol) in water (60 mL). The reaction mixture was heated under reflux for 3 hours, and concentrated to dryness under reduced pressure. The obtained white solid was suspended in EtOH in water (130 mL, 90%), heated for 30 minutes, cooled to room temperature, and collected by filtration, giving sodium prop-2-ene-1-sulfonate (14 g, 76%); 1H NMR (500 MHz, D2O) delta 3.55 (d, J=7.3 Hz, 2H), 5.35-5.41 (m, 2H), 5.85-6.00 (m, 1H). To a stirred solution of sulfonate obtained from step 1 (12.0 g, 84 mmol) in water (48 mL) was added bromine (about 4.5 mL) dropwise with stirring until the solution turned pale brown. The solution was stirred at room temperature for 3 hours. A small amount of Na2SO3 was added to destroy the excess bromine. The solvent was then removed in vacuo and a white solid was obtained. Without further purification, the 2,3-dibromo-1-propanesulfonate was treated with concentrated HCl (50 mL) by stirring at room temperature for 1 day. The precipitate (inorganic salt) was removed by filtration. The filtrate was concentrated to yellow syrup. Without further purification, the syrup residue was subjected to vacuum distillation at 140-150 C. to give 2-bromo-1,3-propane sultone (6.5 g, 32%); 1H NMR (500 MHz, CDCl3) delta 3.52 (dd, J=14.0 & 7.0 Hz, 1H), 3.88 (dd, J=14.0 & 7.0 Hz, 1H), 4.50-4.60 (m, 1H), 4.70-4.82 (m, 2H). To a solution of 2-bromo-1,3-propane sultone (obtained in Step 2, 8.0 g, 39.80 mmol) in toluene (200 mL) was added NEt3 (9 mL, 65 mmol). The reaction mixture was stirred for 3 h (or until complete consumption of the starting material), diluted with an aqueous solution of HCl (1 M), and extracted twice with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give 1,3-prop-1-ene sultone (4.5 g, 94%) as a white solid; 1H NMR (500 MHz, CDCl3) delta 5.11 (dd, J=2.2 & 2.2 Hz, 2H), 6.80 (dt, J=6.6 & 2.2 Hz, 1H), 7.00 (dt, J=6.6 & 2.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta 72.54, 124.76, 137.04. To a solution of 1,3-prop-1-ene sultone (obtained in step 3, 36 mg, 3 mmol) in THF (5 mL) was added tert-butylamine (316 muL, 3 mmol). The reaction mixture was refluxed for 4 h, and then concentrated to dryness. The residual solid material was suspended in a solvent mixture of EtOH, acetone and ether, heated for 15 minutes, and cooled to room temperature. The solid was collected by filtration, washed with ether then dried, providing the title compound (130 mg, 22%); 1H NMR (500 MHz, D2O) delta 1.24 (s, 9H), 4.00 (d, J=7.0 Hz, 2H), 5.94 (m, 1H), 6.50 (d, J=11.0 Hz, 1H). 13C NMR (125 MHz, D2O) delta 25.08, 37.84, 57.63, 127.81, 136.08. ES-MS 192 (M-1).

References: [1]Chemical Communications,1997,p. 611 - 612.
[2]Tetrahedron,1999,vol. 55,p. 2245 - 2262.
[3]Synthesis,2003,p. 1329 - 1334.
[4]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 173-174.
[5]Synlett,1998,p. 1411 - 1413.

8
[ 21806-61-1 ]
[ 78-79-5 ]
(+/-)-6-methyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]
(+/-)-5-methyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]

References: [1]Chemical Communications,1997,p. 611 - 612.
[2]Tetrahedron,1999,vol. 55,p. 2245 - 2262.

9
[ 219952-30-4 ]
[ 21806-61-1 ]

References: [1]Synlett,1998,p. 1411 - 1413.

10
[ 2004-70-8 ]
[ 21806-61-1 ]
(+/-)-4-methyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]
(+/-)-7-methyl-3a,4,7,7a-tetrahydro-2,1-oxathiaindene 1,1-dioxide [ No CAS ]

References: [1]Tetrahedron,1999,vol. 55,p. 2245 - 2262.

12
[ 21806-61-1 ]
[ 2627-86-3 ]
[ 350506-88-6 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 3121 - 3124.

13
[ 21806-61-1 ]
[ 100-46-9 ]
[ 240115-51-9 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 3121 - 3124.

14
[ 7459-72-5 ]
[ 21806-61-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	Grubbs catalyst first generation; In dichloromethane; for 2h;Heating / reflux;Product distribution / selectivity;	Preparation of 6-(aminomethyl)-3,4-dimethylcyclohex-3-ene-1-sulfonic acid (Compound N1); To a cold (-40 C.) solution of allyl alcohol (20 ml, 300 mmol) and NEt3 (26 mL, 186 mmol) in THF (150 mL) was added dropwise 2-chloroethanesulfonyl chloride (10.4 mL, 100 mmol). The reaction was stirred at -40 to -20 C. for 5 hours, quenched with HCl (1M) and extracted with EtOAc. The organic layer was washed with water and dried over Na2SO4. The product was purified by column chromatography using Hexanes/EtOAc 80/20 as eluant to afford allyl vinylsulfonate as a yellowish oil (7 g, 47%). 1H NMR (500 MHz, CDCl3) delta 4.55 (m, 2H), 5.34 (m, 2H), 5.85 (m, 1H), 6.06 (d, J=6.0 Hz, 1H), 6.35 (d, J=17.0 Hz, 1H), 6.50 (dd, J=17 & 9.5 Hz, 1H). To a degassed (by Nitrogen bubbling) solution of allyl vinylsulfonate (3 g, 20.24 mmol) in CH2Cl2 (1 L) was added Grubbs Catalyst (170 mg, 0.2 mmol). The reaction was heated at reflux for 2 h then concentrated. The residual material was applied on silica gel column using Hexanes/EtOAc 80/20 to 50/50 as eluant to afford 1,3-prop-1-ene sultone 2.2 g (92%). 1H NMR (500 MHz, CDCl3) delta 5.11 (dd, J=2.2 & 2.2 Hz, 2H), 6.80 (dt, J=6.6 & 2.2 Hz, 1H), 7.00 (dt, J=6.6 & 2.0 Hz, 1H); 3C NMR (125 MHz, CDCl3) delta 72.54, 124.76, 137.04. A mixture of 1,3-propene sultone (1.44 g, 12 mmol), 2,3-dimethyl-1,3-butanediene (9.5 mL, 84 mmol) in 30 mL of toluene was placed in a sealed tube and heated at 150 C. for 15 hours. The solvent was removed and the residual material was applied on silica gel column using Hexanes/EtOAc 80:20 to 70:30 as eluant to afford 700 mg (86%) of the Diels-Alder adduct. 1H NMR (500 MHz, CDCl3) delta 1.62 (s, 3H), 1.66 (s, 3H), 1.88-1.92 (m, 1H), 2.28-2.42 (m, 3H), 3.12-3.18 (m, 1H), 3.48 (q, J=7.6 Hz, 1H), 3.96 (t, J=8.5 Hz, 1H), 4.40 (dd, J=8.50 & 7.25 Hz, 1H). 13C NMR (125 MHz, CDCl3) delta 19.13, 19.25, 27.20, 30.79, 34.18, 53.04, 72.61, 122.70, 123.44. To an ice-cooled solution of NH4OH (28% in water, 22 mL, 168 mmol) in a co-solvent of THF and EtOH (20 mL, v/v=1:1) was added slowly via a syringe pump a solution of the Diels-Alder adduct from step 3 (680 mg, 3.36 mmol). After the addition (2 h), the reaction was stirred for two more hours until TLC indicated complete consumption of the starting material. The solvent was evaporated and the resulting solid was suspended in mixed solvents of EtOH, acetone and ether, heated for 15 minutes and cooled. The solid was collected by filtration, washed with ether and dried, to give the title compound (450 mg, 61%). 1H NMR (500 MHz, D2O) delta 1.49 (s, 3H), 1.52 (s, 3H), 1.86-1.92 (m, 1H), 2.14-2.28 (m, 3H), 2.44-2.49 (m, 1H), 2.80 (dd, J=13.0 & 6.0 Hz, 1H), 3.10-3.16 (m, 1H), 3.27 (dd, J=14.0 & 6.0 Hz, 1H); 13C NMR (125 MHz, D2O) delta 18.02, 18.28, 28.93, 32.36, 34.69, 38.79, 57.85, 123.09, 123.72. ES-MS 218 (M-1).

References: [1]Synlett,2003,p. 667 - 670.
[2]Tetrahedron,2006,vol. 62,p. 9017 - 9037.
[3]Synlett,2002,p. 2019 - 2022.
[4]Synthesis,2004,p. 1696 - 1712.
[5]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 172-173.
[6]Chemistry - A European Journal,2015,vol. 21,p. 6906 - 6912.

15
[ 21806-61-1 ]
C₂₄H₁₇NO₂ [ No CAS ]
2-((3S,3aS,6aS)-4,4-Dioxo-3-pyren-1-yl-tetrahydro-1,5-dioxa-4λ⁶-thia-2-aza-pentalen-2-ylmethyl)-phenol [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 2884 - 2885.

16
[ 24423-88-9 ]
[ 21806-61-1 ]
(+/-)-(3aR,8aS,8bS)-octahydro[3,4-d]pyrrolo[2,3-a]pyridine[1,2-b]isoxazol-2,1-oxathiain-1,1-dioxide [ No CAS ]