(N-Crotonyl)-(2S)-bornane-10,2-sultam

Base Information

• Chemical Name: (N-Crotonyl)-(2S)-bornane-10,2-sultam
• CAS No.: 94594-81-7
• Molecular Formula: C14H21NO3S
• Molecular Weight: 283.39
• Hs Code.: 2934999090
• European Community (EC) Number: 635-626-9
• DSSTox Substance ID: DTXSID20448960
• Nikkaji Number: J1.008.253F,J1.490.492A,J888.072G
• Wikidata: Q82268198
• Mol file: 94594-81-7.mol

Synonyms:94594-81-7;(N-Crotonyl)-(2S)-bornane-10,2-sultam;(S)-(+)-(2-Butenoyl)-2,10-camphorsultam;(E)-1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]but-2-en-1-one;(S)-(+)-(2-Butenoyl)-2 10-camphorsultam;N-Crotonyl-(2S)-bornane 10,2-sultam;SCHEMBL23977524;DTXSID20448960;MFCD00269665;AKOS027470096;AS-49357;E84033;(S)-(+)-(2-Butenoyl)-2,10-camphorsultam, 97%;(1R,4S)-2beta-[[(E)-2-Butenoyl]amino]-7,7-dimethylbicyclo[2.2.1]heptane-1-methanesulfonic acid sultam;(1R,5S,7S)-4-[(2E)-but-2-enoyl]-10,10-dimethyl-3|E?-thia-4-azatricyclo[5.2.1.0?,?]decane-3,3-dione;(3aR,7abeta)-1-(2-Butenoyl)-8,8-dimethylhexahydro-3H-3aalpha,6alpha-methano-2,1-benzisothiazole 2,2-dioxide;(E)-1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)but-2-en-1-one;(E)-1-((3AR,6S,7AS)-8,8-DIMETHYL-2,2-DIOXIDOTETRAHYDRO-3H-3A,6-METHANOBENZO[C]ISOTHIAZOL-1(4H)-YL)BUT-2-EN-1-ONE

Chemical Property of (N-Crotonyl)-(2S)-bornane-10,2-sultam

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 182-185 °C(lit.)
• Refractive Index: 1.576
• Boiling Point: 397.2 °C at 760 mmHg
• Flash Point: 194 °C
• PSA: 62.83000
• Density: 1.27 g/cm³
• LogP: 2.94810
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 283.12421471
• Heavy Atom Count: 19
• Complexity: 558

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(+)-(2-Butenoyl)-2,10-camphorsultam 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)N1C2CC3CCC2(C3(C)C)CS1(=O)=O
• Isomeric SMILES: C/C=C/C(=O)N1[C@H]2C[C@@H]3CC[C@]2(C3(C)C)CS1(=O)=O

Technology Process of (N-Crotonyl)-(2S)-bornane-10,2-sultam

There total 7 articles about (N-Crotonyl)-(2S)-bornane-10,2-sultam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + (+)-camphorsultam (108448-77-7,124224-04-0) → (E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one (94594-81-7)

Guidance literature:

With sodium hydride; In toluene; at 20 ℃;

DOI:10.1021/ol006679t

Reference yield: 86.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + (+)-(1R,5S)-N-(trimethylsilyl)bornane-2,10-sultam (124170-22-5,143167-58-2) → (E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one (94594-81-7)

Guidance literature:

With copper dichloride; In toluene; for 16h; Heating;

DOI:10.1055/s-1992-26169

Reference yield:

(R)-10-camphorsulfonic acid (35963-20-3,61380-66-3) → (E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one (94594-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂

2: NH₃ / dioxane; H₂O

3: 100 percent / NaBH₄ / methanol; H₂O

4: 90 percent / NaH / toluene; various solvent(s) / 20 °C

With sodium tetrahydroborate; thionyl chloride; ammonia; sodium hydride; In 1,4-dioxane; methanol; water; toluene;

DOI:10.1021/ol006679t

upstream raw materials:

trans-chrotonyl chloride

(+)-camphorsultam

(+)-(1R,5S)-N-(trimethylsilyl)bornane-2,10-sultam

(R)-10-camphorsulfonic acid

Downstream raw materials:

1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-butan-1-one

<3aR-<1(4S^*,5S^*),3aα,6α,7aβ>>-1-<(4,5-dihydro-4-methyl-3-phenyl-5-isoxazolyl)carbonyl>hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

<3aR-<1(4R^*,5R^*),3aα,6α,7aβ>>-1-<(4,5-dihydro-4-methyl-3-phenyl-5-isoxazolyl)carbonyl>hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

<3aR-<1(4R^*,5S^*),3aα,6α,7aβ>>-1-<(4,5-dihydro-4-methyl-3-phenyl-5-isoxazolyl)carbonyl>hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide