(+/-)-14-oxo-1,2-dehydrocacalol methyl ether

Base Information

Chemical Name:(+/-)-14-oxo-1,2-dehydrocacalol methyl ether
CAS No.:676562-84-8
Molecular Formula:C₁₆H₁₆O₃
Molecular Weight:256.301
Hs Code.:

Synonyms:

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Chemical Property of (+/-)-14-oxo-1,2-dehydrocacalol methyl ether

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Technology Process of (+/-)-14-oxo-1,2-dehydrocacalol methyl ether

There total 17 articles about (+/-)-14-oxo-1,2-dehydrocacalol methyl ether 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%

: 676562-83-7
(+/-)-14-oxocacalol methyl ether

: 65080-24-2
maturinin

: 676562-84-8,64185-53-1
(+/-)-14-oxo-1,2-dehydrocacalol methyl ether

: (5R,8R)-8-Hydroxy-9-methoxy-3,5-dimethyl-5,6,7,8-tetrahydro-naphtho[2,3-b]furan-4-carbaldehyde

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 0 - 20 ℃; for 3h;
DOI:10.1246/cl.2004.136

Reference yield: 37.0%

: (5R,8R)-8-Hydroxy-9-methoxy-3,5-dimethyl-5,6,7,8-tetrahydro-naphtho[2,3-b]furan-4-carbaldehyde

: 676562-84-8,64185-53-1
(+/-)-14-oxo-1,2-dehydrocacalol methyl ether

Guidance literature:: With Burgess Reagent; In benzene; at 20 ℃;
DOI:10.1246/cl.2004.136

Reference yield:

: 2859-78-1
4-Bromoveratrole

: 676562-84-8,64185-53-1
(+/-)-14-oxo-1,2-dehydrocacalol methyl ether

Guidance literature:: Multi-step reaction with 14 steps

1.1: AlCl₃ / 1,1,2,2-tetrachloro-ethane / 70 °C

1.2: AcCl / methanol / 14 h / 20 °C

1.3: 54 percent / K₂CO₃ / acetone / 46 h / Heating

2.1: 97 percent / NaOH / methanol / 24 h / 40 °C

3.1: 64 percent / (CF₃CO)2O / trifluoroacetic acid / 3 h / 40 °C

4.1: 98 percent / BBr₃ / CH₂Cl₂ / 18 h / -78 - -40 °C

5.1: 86 percent / Li₂CO₃ / 17 h / 70 °C

6.1: 77 percent / K₂CO₃ / acetone / 14 h / Heating

7.1: 52 percent / NaBH₄ / trifluoroacetic acid / 4 h / 0 - 20 °C

8.1: 96 percent / NaBH₄ / methanol / 14 h / 20 °C

9.1: 97 percent / iPr₂NEt / CH₂Cl₂

10.1: nBuLi / tetrahydrofuran / -78 °C

10.2: 90 percent / tetrahydrofuran / 1 h

11.1: 100 percent / HCl / tetrahydrofuran / 40 °C

12.1: 84 percent / DMSO; (COCl)2; Et₃N

13.1: 99 percent / CF₃SO₃H / CH₂Cl₂ / 5 h / 0 - 20 °C

14.1: 23 percent / DDQ / benzene / 3 h / 0 - 20 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; aluminium trichloride; oxalyl dichloride; trifluorormethanesulfonic acid; boron tribromide; lithium carbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; acetone; trifluoroacetic acid; 1,1,2,2-tetrachloroethane; benzene; 1.1: Friedel-Crafts alkylation / 3.1: Friedel-Craft acylation / 12.1: Swern oxidation;
DOI:10.1246/cl.2004.136