methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

Base Information

Chemical Name:methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate
CAS No.:1262726-29-3
Molecular Formula:C₁₆H₁₄I₂O₂
Molecular Weight:492.095
Hs Code.:

Synonyms:methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

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Chemical Property of methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

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Technology Process of methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

There total 9 articles about methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate 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: 46.0%

: (1RS,4SR,7SR)-[7-benzyl-3-iodo-7-(methoxycarbonyl)bicyclo[2.2.1]hepta-2,5-dien-2-yl](phenyl)iodonium triflate

: 1262726-29-3
methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

Guidance literature:: With copper(l) iodide; sodium iodide; In acetonitrile; at -40 - 20 ℃;
DOI:10.3998/ark.5550190.0012.310

Reference yield: 35.0%

: (1RS,4SR,7SR)-[7-benzyl-3-iodo-7-(methoxycarbonyl)bicyclo[2.2.1]hepta-2,5-dien-2-yl](phenyl)iodonium triflate

: methyl (1RS,4SR,5SR,7RS)-7-benzyl-5-iodo-6-oxobicyclo[2.2.1]hept-2-ene-7-carboxylate

: 1262726-29-3
methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

Guidance literature:: With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 18h;
DOI:10.3998/ark.5550190.0012.310

Reference yield:

: 1262726-19-1
methyl 1-benzyl-2-(trimethylsilyloxy)cyclopent-2-enecarboxylate

: 1262726-29-3
methyl (1R,4S,7s)-7-benzyl-2,3-diiodobicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: oxygen; palladium diacetate / dimethyl sulfoxide / 24 h / 20 °C

2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0 - 20 °C

3: toluene-4-sulfonic acid / benzene / 18 h / Reflux

4: acetonitrile / 68 h / 20 °C

5: copper(l) iodide; sodium iodide / acetonitrile / -40 - 20 °C

With sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride heptahydrate; oxygen; palladium diacetate; toluene-4-sulfonic acid; sodium iodide; In methanol; dimethyl sulfoxide; acetonitrile; benzene; 2: Luche reduction / 4: Diels-Alder reaction;
DOI:10.3998/ark.5550190.0012.310