(1alpha,6alpha)-2-Acetyl-9-tosyl-9-azabicyclo[4.2.1]nona-2-ene

Base Information

Chemical Name:(1alpha,6alpha)-2-Acetyl-9-tosyl-9-azabicyclo[4.2.1]nona-2-ene
CAS No.:225779-62-4
Molecular Formula:C₁₇H₂₁NO₃S
Molecular Weight:319.425
Hs Code.:
DSSTox Substance ID:DTXSID601133256
Nikkaji Number:J1.104.878A

Synonyms:DTXSID601133256;(1alpha,6alpha)-2-Acetyl-9-tosyl-9-azabicyclo[4.2.1]nona-2-ene;1-[(1S,6S)-9-[(4-Methylphenyl)sulfonyl]-9-azabicyclo[4.2.1]non-2-en-2-yl]ethanone;225779-62-4

Suppliers and Price of (1alpha,6alpha)-2-Acetyl-9-tosyl-9-azabicyclo[4.2.1]nona-2-ene

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1alpha,6alpha)-2-Acetyl-9-tosyl-9-azabicyclo[4.2.1]nona-2-ene

Chemical Property:

XLogP3:2.5
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:319.12421471
Heavy Atom Count:22
Complexity:567

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1=CC=C(C=C1)S(=O)(=O)N2C3CCC=C(C2CC3)C(=O)C
Isomeric SMILES:CC1=CC=C(C=C1)S(=O)(=O)N2[C@H]3CCC=C([C@@H]2CC3)C(=O)C

Technology Process of (1alpha,6alpha)-2-Acetyl-9-tosyl-9-azabicyclo[4.2.1]nona-2-ene

There total 30 articles about (1alpha,6alpha)-2-Acetyl-9-tosyl-9-azabicyclo[4.2.1]nona-2-ene 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: 85.0%

: 916152-75-5
2-[(1S,6S)-9-(Toluene-4-sulfonyl)-9-aza-bicyclo[4.2.1]non-2-en-2-yl]-propane-1,2-diol

: 225779-62-4
(+)-N-tosylanatoxin-a

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 1.5h;
DOI:10.1016/j.tet.2006.05.088

Reference yield:

: C₁₈H₂₅NO₄S

: 143264-77-1
(-)-N-tosylanatoxin-a

: 225779-62-4
(+)-N-tosylanatoxin-a

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; (+)-(2S,5S)-2,5-diphenyltetrahydrothiophene; In acetonitrile; at -20 ℃; for 22h; Reagent/catalyst; Temperature; Overall yield = 53 percent; enantioselective reaction; Inert atmosphere;
DOI:10.1002/anie.202004464

Reference yield:

: trans/cis-1-bromo-5-(N-tosylamido)-8-acetoxy-(E)-cyclooctene

: 225779-62-4
(+)-N-tosylanatoxin-a

Guidance literature:: Multi-step reaction with 11 steps

1: 72 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

2: 100 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

3: Ph₃P, diisopropyl azodicarboxylate / benzene / 3 h / Ambient temperature

4: 70 percent / Pd(PPh₃)4, Et₃N, DMPU / 14 h / 100 °C / 31028.9 Torr

5: 100 percent / K₂CO₃ / methanol / 0.33 h / Ambient temperature

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 s, 2.) THF, hexane, from -78 deg C to RT

7: 95 percent / TFA / CH₂Cl₂ / 1 h / Ambient temperature

8: S,S-1-(2-diphenylphosphinobenzamido)-2-(2-picolinamido)cyclohexane, Pd₂(dba)3CHCl₃ / CH₂Cl₂ / 14 h / 0 °C

9: aq. LiOH / tetrahydrofuran / 4 h / Ambient temperature

10: 1.) NaH, 2.) (COCl)2 / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, RT, 1.5 h

11: 1.) AlCl₃ / 1.) CH₂Cl₂, -50 deg C, 1 h, 2.) CH₂Cl₂, toluene, RT, 2 h

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; aluminium trichloride; oxalyl dichloride; di-isopropyl azodicarboxylate; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; S,S-1-(2-diphenylphosphinobenzamido)-2-(2-picolinamido)cyclohexane; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/ja983617d