(R)-(-)-Acryloyl-2,10-camphorsultam

Base Information

• Chemical Name: (R)-(-)-Acryloyl-2,10-camphorsultam
• CAS No.: 94594-91-9
• Molecular Formula: C₁₃H₁₉NO₃S
• Molecular Weight: 269.365
• DSSTox Substance ID: DTXSID701107953
• Nikkaji Number: J430.774G,J875.113G
• Mol file: 94594-91-9.mol

Synonyms:94594-91-9;(R)-(-)-Acryloyl-2,10-camphorsultam;1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one;Oppolzer's caMphor sultaM;DTXSID701107953;E85542;(1S,4R)-2alpha-(Acryloylamino)bornane-10-sulfonic acid sultam;(7aalpha)-1-Propenoyl-3abeta,6beta-isopropylideneoctahydro-2,1-benzoisothiazole 2,2-dioxide;(1S,5R,7R)-10,10-dimethyl-4-(prop-2-enoyl)-3|E?-thia-4-azatricyclo[5.2.1.0?,?]decane-3,3-dione;1-[(1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]prop-2-en-1-one;1-[(3aS,6R,7aR)-Tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-propen-1-one

Chemical Property of (R)-(-)-Acryloyl-2,10-camphorsultam

Chemical Property:

• Melting Point: 203-205 °C(Solv: ethanol (64-17-5))
• Boiling Point: 382.1±25.0 °C(Predicted)
• PKA: -14.54±0.40(Predicted)
• PSA: 62.83000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 2.55800
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 269.10856464
• Heavy Atom Count: 18
• Complexity: 531

Purity/Quality:

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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC13CS(=O)(=O)N(C3C2)C(=O)C=C)C
• Isomeric SMILES: CC1([C@@H]2CC[C@]13CS(=O)(=O)N([C@@H]3C2)C(=O)C=C)C

Technology Process of (R)-(-)-Acryloyl-2,10-camphorsultam

There total 13 articles about (R)-(-)-Acryloyl-2,10-camphorsultam 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%

acryloyl chloride (814-68-6,25189-84-8) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → acrylcamphorsultam (94594-91-9)

Guidance literature:

With pyridine;

Reference yield: 18.5%

3-benzyloxy-2-bromopropanoyl bromide (167872-57-3) + N-trimethylsilylbornane-10,2-sultam (167934-73-8) → acrylcamphorsultam (94594-91-9)

Guidance literature:

In acetonitrile; at 40 ℃; for 48h;

DOI:10.1016/0957-4166(95)00032-K

Reference yield:

acrylic acid anhydride (2051-76-5) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → acrylcamphorsultam (94594-91-9)

Guidance literature:

With lithium chloride; In tetrahydrofuran; Yield given; Ambient temperature;

DOI:10.1021/jo00112a060

upstream raw materials:

acryloyl chloride

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

3-benzyloxy-2-bromopropanoyl bromide

N-trimethylsilylbornane-10,2-sultam

Downstream raw materials:

(3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-(3-phenyl-2-trimethylsilanyloxy-isoxazolidin-5-yl)-methanone

3-<(1S)-N-(tert-butyloxycarbonyl)amino-2-phenylethyl>-5-<(2R)-(bornane-10,2-sultamyl)-N-carbonyl>-(5R)-Δ²-isoxazoline

{(S)-1-[(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-4,5-dihydro-isoxazol-3-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Refernces

• 1、 -. "Conjugate of cytotoxin molecule and cell binding receptor molecule". Paragraph 0035. . Retrieved 2019/10/10.
• 2、 Neisius, N. Matthias,Plietker, Bernd. "Diastereoselective ru-catalyzed cross-metathesis-dihydroxylation sequence. An efficient approach toward enantiomerically enriched syn-diols". . p. 3218 - 3227. Retrieved 2008/09/19.