(E)-1-[(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

Base Information

• Chemical Name: (E)-1-[(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
• CAS No.: 94668-55-0
• Molecular Formula: C14H21 N O3 S
• Molecular Weight: 283.39
• European Community (EC) Number: 635-629-5
• Mol file: 94668-55-0.mol

Synonyms:(R)-(-)-(2-Butenoyl)-2,10-camphorsultam;94668-55-0

Chemical Property of (E)-1-[(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

Chemical Property:

• Vapor Pressure: 1.62E-06mmHg at 25°C
• Melting Point: 180-184 °C(lit.)
• Refractive Index: 1.576
• Boiling Point: 397.2°Cat760mmHg
• PKA: -14.19±0.40(Predicted)
• Flash Point: 194°C
• PSA: 62.83000
• Density: 1.27g/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

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

Safty Information:

• 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]3CCC2(C3(C)C)CS1(=O)=O
• Uses: (R)-(-)-(2-Butenoyl)-2,10-camphorsultam can be used: In the asymmetric total synthesis of lycopodine via diastereoselective cyclization and intramolecular Mannich cyclization. To prepare (S)-4,4-dichloro-3-methylbutanoic acid, which is utilized as a key intermediate for the total synthesis of dysideaproline E.

Technology Process of (E)-1-[(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

There total 13 articles about (E)-1-[(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 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: 89.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → (1S)-N-crotyl-2,10-camphorsultam (94668-55-0)

Guidance literature:

With copper dichloride; In benzene; for 1h; Heating;

DOI:10.1016/S0040-4020(03)00853-6

Reference yield: 87.0%

trans-crotonic anhydride (623-68-7) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → (1S)-N-crotyl-2,10-camphorsultam (94668-55-0)

Guidance literature:

With triethylamine; lithium chloride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jo00112a060

Reference yield: 76.0%

trans-but-2-enyl chloride (4894-61-5) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → (1S)-N-crotyl-2,10-camphorsultam (94668-55-0)

Guidance literature:

(2R)-bornane-10,2-sultam; In toluene; mineral oil; at 0 - 20 ℃; for 0.75h;

trans-but-2-enyl chloride; In toluene; mineral oil; at 0 - 20 ℃; for 2.25h;

DOI:10.1002/chem.201800046

upstream raw materials:

trans-chrotonyl chloride

(2R)-bornane-10,2-sultam

trans-crotonic anhydride

1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.0^1.5]dec-4-yl]-ethanone

Downstream raw materials:

(-)-N-[(1'R,6'R)-6-methyl-3-cyclohexenylcarbonyl]bornane-10,2-sultam

C₁₆H₂₂O₃

(2R)-bornane-10,2-sultam

Refernces

• 1、 Khrimian, Ashot,Margaryan, Armenak Kh.,Schmidt, Walter F.. "An improved synthesis of ethyl cis-5-iodo-trans-2-methylcyclohexanecarboxylate, a potent attractant for the Mediterranean fruit fly". . p. 5475 - 5480. Retrieved 2007/10/03.
• 2、 Harding, John R.,Hughes, Rachael A.,Kelly, Nicholas M.,Sutherland, Andrew,Willis, Christine L.. "Syntheses of isotopically labelled L-?±-amino acids with an asymmetric centre at C-3". . p. 3406 - 3416. Retrieved 2007/10/03.