Cyclobuta[1,2:3,4]dicyclopenten-1(2H)-one, octahydro-3a-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (3aalpha,3balpha,6aalpha,6balpha)-

Base Information

• Chemical Name: Cyclobuta[1,2:3,4]dicyclopenten-1(2H)-one, octahydro-3a-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (3aalpha,3balpha,6aalpha,6balpha)-
• CAS No.: 119245-18-0
• Molecular Formula: C₁₈H₂₂O₄S
• Molecular Weight: 334.436
• DSSTox Substance ID: DTXSID801106322
• Mol file: 119245-18-0.mol

Synonyms:DTXSID801106322;119245-18-0;Cyclobuta[1,2:3,4]dicyclopenten-1(2H)-one, octahydro-3a-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (3aalpha,3balpha,6aalpha,6balpha)-

Chemical Property of Cyclobuta[1,2:3,4]dicyclopenten-1(2H)-one, octahydro-3a-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (3aalpha,3balpha,6aalpha,6balpha)-

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.12388035
• Heavy Atom Count: 23
• Complexity: 585

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC23CCC(=O)C2C4C3CCC4

Technology Process of Cyclobuta[1,2:3,4]dicyclopenten-1(2H)-one, octahydro-3a-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (3aalpha,3balpha,6aalpha,6balpha)-

There total 4 articles about Cyclobuta[1,2:3,4]dicyclopenten-1(2H)-one, octahydro-3a-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (3aalpha,3balpha,6aalpha,6balpha)- 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: 58.0%

3a-Hydroxymethyl-octahydro-cyclobutadicyclopenten-1-one (119245-17-9,131321-90-9) + p-toluenesulfonyl chloride (98-59-9) → 6-<<(p-tolylsulfonyl)oxy>methyl>tricyclo<5.3.0.02,6>-3-decanone (119245-18-0,119324-02-6)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 18h;

DOI:10.1021/jo00269a012

Reference yield:

methyl 8-oxotricyclo<5.3.0.02,6>decane-1-carboxylate (159572-82-4) → 6-<<(p-tolylsulfonyl)oxy>methyl>tricyclo<5.3.0.02,6>-3-decanone (119245-18-0,119324-02-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / p-toluenesulfonic acid / toluene / 4.5 h / Heating

2: LiAlH₄ / diethyl ether / 2 h / Heating

3: 1 M aq. H₂SO₄ / diethyl ether / 2 h / Ambient temperature

4: 58 percent / pyridine / 18 h / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; sulfuric acid; toluene-4-sulfonic acid; In diethyl ether; toluene;

DOI:10.1021/jo00269a012

Reference yield:

C14H20O4 (119245-15-7,119324-05-9,133162-52-4) → 6-<<(p-tolylsulfonyl)oxy>methyl>tricyclo<5.3.0.02,6>-3-decanone (119245-18-0,119324-02-6)

Guidance literature:

Multi-step reaction with 3 steps

1: LiAlH₄ / diethyl ether / 2 h / Heating

2: 1 M aq. H₂SO₄ / diethyl ether / 2 h / Ambient temperature

3: 58 percent / pyridine / 18 h / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; sulfuric acid; In diethyl ether;

DOI:10.1021/jo00269a012

upstream raw materials:

3a-Hydroxymethyl-octahydro-cyclobutadicyclopenten-1-one

p-toluenesulfonyl chloride

methyl 8-oxotricyclo<5.3.0.0^2,6>decane-1-carboxylate

C₁₄H₂₀O₄

Downstream raw materials:

(+/-)-tricyclo<6.3.0.0^2,6>-2(6)-undecen-3-one

(+/-)-1-<(p-tolylsulfonyl)oxy>tricyclo<5.3.1.0^2,6>-8-undecanone