<1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

Base Information

Chemical Name:<1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one
CAS No.:115463-47-3
Molecular Formula:C₁₉H₂₄O₄
Molecular Weight:316.397
Hs Code.:

Synonyms:<1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

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Chemical Property of <1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

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Technology Process of <1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

There total 2 articles about <1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one 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: 41.0%

: 90-24-4
2-hydroxy-4,6-dimethoxyacetophenone

: 38651-65-9
(1R,5S)-(+)-nopinone

: 115481-66-8
2-[(1R,5S)-6,6-Dimethyl-bicyclo[3.1.1]hept-(2E)-ylidene]-1-(2-hydroxy-4,6-dimethoxy-phenyl)-ethanone

: 115510-71-9
2,3-dihydro-5,7-dimethoxy-2-(6,6-dimethylbicyclo<3.1.1.>-2-heptylidene)-4H-1-benzopyran-4-one

: 115463-47-3
<1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

Guidance literature:: With pyrrolidine; In benzene; Yields of byproduct given;
DOI:10.1021/ja00223a062

Reference yield:

: 38651-65-9
(1R,5S)-(+)-nopinone

: 115463-47-3
<1'R-(1'α,2'α,5'α)>-5,7-dimethoxy-6',6'-dimethylspiro<2H-1-benzopyran-2,2'-bicyclo<3.1.1>heptan>-4(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / NaH / tetrahydrofuran / 20 h / 50 °C

2: 95 percent / DIBAL-H / toluene / 0.25 h / -78 °C

3: 95 percent / N-methyl morpholine N-oxide, tetra-N-propylammonium perruthenate, 4 A mecular sieves / 0.08 h / Ambient temperature

4: 1.) phenylboronic acid, propanoic acid, 2.) H₂, 3.) ceric ammonium nitrate / 2.) 10percent Pd/C

With tetrapropylammonium perruthennate; ammonium cerium(IV) nitrate; 4 A molecular sieve; hydrogen; sodium hydride; diisobutylaluminium hydride; propionic acid; 4-methylmorpholine N-oxide; phenylboronic acid; palladium on activated charcoal; In tetrahydrofuran; toluene;
DOI:10.1139/v94-237