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

Base Information

• Chemical Name: N-Propionyl-(2R)-bornane-10,2-sultam
• CAS No.: 125664-95-1
• Molecular Formula: C13H21NO3S
• Molecular Weight: 271.381
• DSSTox Substance ID: DTXSID00451412
• Nikkaji Number: J430.703H
• Wikidata: Q82271422
• Mol file: 125664-95-1.mol

Synonyms:125664-95-1;N-Propionyl-(2R)-bornane-10,2-sultam;1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one;N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM;1-[(1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]propan-1-one;1-Propanone, 1-[(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-;DTXSID00451412;JEMOGQYNLSWGPL-GIPNMCIBSA-N;AKOS016013074;AC-28350;AM20120714;CS-0166793;(3aS,6R,7aR)-8,8-Dimethyl-1-propanoylhexahydro-3a,6-methano-2lambda~6~-2lambda~6~,1-benzothiazole-2,2(3H)-dione;1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)propan-1-one

Chemical Property of N-Propionyl-(2R)-bornane-10,2-sultam

Chemical Property:

• Melting Point: 153-154 °C(Solv: methanol (67-56-1))
• Boiling Point: 384.8±25.0 °C(Predicted)
• PKA: -14.14±0.40(Predicted)
• PSA: 62.83000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 2.78200
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 271.12421471
• Heavy Atom Count: 18
• Complexity: 505

Purity/Quality:

98%min ^*data from raw suppliers

1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of N-Propionyl-(2R)-bornane-10,2-sultam

There total 6 articles about N-Propionyl-(2R)-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: 95.0%

propionic acid anhydride (123-62-6) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → N-propionyl-(2R)-bornane-(10,2)-sultam (125664-95-1)

Guidance literature:

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

DOI:10.1021/jo00112a060

Reference yield: 87.0%

propionyl chloride (79-03-8) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → N-propionyl-(2R)-bornane-(10,2)-sultam (125664-95-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1039/c3ob41569d

Reference yield:

N-<(2R,3S)-3-hydroxy-2-methylbutanoyl>bornane-10,2-sultam (125664-99-5) → N-propionyl-(2R)-bornane-(10,2)-sultam (125664-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O₂, LiOH / 1.) THF, H₂O, 0 deg C

2: 1.) NaH / 1.) toluene, RT, 2 h, 2.) 2 h

With lithium hydroxide; dihydrogen peroxide; sodium hydride;

DOI:10.1021/ja00163a045

upstream raw materials:

propionyl chloride

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

propionic acid anhydride

C₈H₁₄O₃

Downstream raw materials:

[(S)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-3-oxo-propyl]-methyl-carbamic acid benzyl ester

(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-chloro-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-propan-1-one

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-chloro-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-propan-1-one

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-3-(4-nitro-phenyl)-propan-1-one

Refernces

• 1、 Rival, Nicolas,Hanquet, Gilles,Bensoussan, Charlelie,Reymond, Sebastien,Cossy, Janine,Colobert, Francoise. "Diastereoselective synthesis of the C14-C29 fragment of amphidinol 3". . p. 6829 - 6840. Retrieved 2013/10/01.
• 2、 Shklyaruck, Denis,Matiushenkov, Evgenii. "Stereoselective synthesis of (3S,5S,6S)-tetrahydro-6-isopropyl-3,5- dimethylpyran-2-one; A C5-epimer of a component of a natural sex pheromone of the wasp Macrocentrus grandii, the larval parasitoid of the European corn borer Ostrinia nubilalis". scheme or table. p. 1448 - 1454. Retrieved 2011/11/12.