(6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine

Base Information

• Chemical Name: (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine
• CAS No.: 32064-13-4
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397
• Mol file: 32064-13-4.mol

Synonyms:

Chemical Property of (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine

There total 16 articles about (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine 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: 96.0%

Epoxyaurapten (21499-17-2) → (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine (5980-09-6,14957-38-1,31946-96-0,32064-13-4,61347-54-4,130548-21-9)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85097-3

Reference yield:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine (5980-09-6,14957-38-1,31946-96-0,32064-13-4,61347-54-4,130548-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / m-CPBA; K₂CO₃ / CH₂Cl₂ / 24 h / 0 °C

2: 10 percent / NaH / dimethylformamide / 12 h / 20 °C

3: Rhodococcus ruber DSM 43338 / H₂O; various solvent(s) / 216 h / pH 8.0

With Rhodococcus ruber DSM 43338; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2003.10.106

Reference yield:

(R)-6-O-(4-geranyloxy-2-hydroxy)cinnamoylmarmin (142628-36-2) → (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine (5980-09-6,14957-38-1,31946-96-0,32064-13-4,61347-54-4,130548-21-9)

Guidance literature:

With sodium hydroxide; In methanol; at 23 ℃; for 3h;

DOI:10.1016/0031-9422(92)80291-L

upstream raw materials:

auraptene

Epoxyaurapten

(R)-6-O-(4-geranyloxy-2-hydroxy)cinnamoylmarmin

(E)-7-<<5-(3,3-dimethyloxiranyl)-3-methyl-2-pentenyl>oxy>-2H-1-benzopyran-2-one

Refernces

• 1、 Masuda, Toshiya,Muroya, Yukari,Nakatani, Nobuji. "7-HYDROXYCOUMARIN DERIVATIVES FROM THE JUICE OIL OF CITRUS HASSAKU". . p. 1363 - 1366. Retrieved 1992.
• 2、 Ohashi, Kazuyoshi,Watanabe, Hisashi,Ohi, Katsuhide,Arimoto, Hirokazu,Okumura, Yasuaki. "Two New 7-Geranyloxycoumarins from the Bark of Aegle Marmelos, an Indonesian Medicinal Plant". . p. 881 - 882. Retrieved 2007/10/03.