5-(2,3-Dihydroxypropyl)-5'-allylbiphenyl-2,2'-diol

Base Information

• Chemical Name: 5-(2,3-Dihydroxypropyl)-5'-allylbiphenyl-2,2'-diol
• CAS No.: 93673-81-5
• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.354
• Mol file: 93673-81-5.mol

Synonyms:

Chemical Property of 5-(2,3-Dihydroxypropyl)-5'-allylbiphenyl-2,2'-diol

Chemical Property:

• PSA: 80.92000
• LogP: 2.38900

Purity/Quality:

98%Min ^*data from raw suppliers

MagnolignanA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Magnolignan A is a magnolol derivative with potent anticancer activity in non-small cell lung cancer.

Technology Process of 5-(2,3-Dihydroxypropyl)-5'-allylbiphenyl-2,2'-diol

There total 6 articles about 5-(2,3-Dihydroxypropyl)-5'-allylbiphenyl-2,2'-diol 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: 20.0%

Magnolol (528-43-8) → magnolignan A (140866-37-1,93673-81-5)

Guidance literature:

With osmium(VIII) oxide; water; In acetone; tert-butyl alcohol; at 20 ℃; for 24h;

DOI:10.1021/ml300235q

Reference yield:

Magnolol (528-43-8) → 5'-Allyl-5-((S)-2,3-dihydroxy-propyl)-biphenyl-2,2'-diol + magnolignan A (93673-81-5)

Guidance literature:

With AD-mix-α; sodium hydrogencarbonate; In water; tert-butyl alcohol; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(98)00118-9

Reference yield:

4-bromo-phenol (106-41-2) → magnolignan A (93673-81-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / K₂CO₃ / acetone / 2 h / Heating

2: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h

3: 3N aq. HCl / tetrahydrofuran / 3 h / Heating

4: 77 percent / AlCl₃, DDQ / nitromethane / 1.5 h / Ambient temperature

5: NaHCO3, AD-mix-β / 2-methyl-propan-2-ol; H2O / 0 °C

With hydrogenchloride; aluminium trichloride; AD-mix-β; sodium hydrogencarbonate; potassium carbonate; magnesium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; nitromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/S0957-4166(98)00118-9

upstream raw materials:

Magnolol

4-bromo-phenol

4-(prop-2-enyl)phenol

p-methoxymethoxybromobenzene

Refernces

• 1、 Gu, Wenxin,She, Xuegong,Pan, Xinfu,Yang, Teng-Kuei. "Enantioselective syntheses of (S)- and (R)-8,9 dihydroxydihydromagnolol". . p. 1377 - 1380. Retrieved 2007/10/03.