4-HYDROXYMYOPORONE

Base Information

• Chemical Name: 4-HYDROXYMYOPORONE
• CAS No.: 55626-95-4
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 55626-95-4.mol

Synonyms:(+)-4-Hydroxymyoporone;4-Hydroxymyoporone

Chemical Property of 4-HYDROXYMYOPORONE

Chemical Property:

• Vapor Pressure: 5.77E-08mmHg at 25°C
• Boiling Point: 424.5°Cat760mmHg
• Flash Point: 210.6°C
• PSA: 67.51000
• Density: 1.076g/cm³
• LogP: 2.99880

Purity/Quality:

99%min ^*data from raw suppliers

4-HYDROXYMYOPORONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-HYDROXYMYOPORONE

There total 13 articles about 4-HYDROXYMYOPORONE 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: 17.0%

(R)-1-Furan-3-yl-4,8-dimethyl-nonane-1,4,6-triol (247256-65-1) → athanagrandione (55626-95-4)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0031-9422(00)80452-5

Reference yield:

(3S,1'S,2'S)-1-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)hex-5-en (214959-70-3) → athanagrandione (55626-95-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: O₃ / CH₂Cl₂; methanol / -78 °C

1.2: 95 percent / PPh₃ / 0.5 h / -78 °C

2.1: 96 percent / tetrahydrofuran; diethyl ether / 4 h / -78 - 20 °C

3.1: 95 percent / Na; NH₃ / tetrahydrofuran / 0.5 h / -78 °C

4.1: 86 percent / p-TsOH / CH₂Cl₂ / 1 h / 20 °C

5.1: 99 percent / TBAF*3H₂O / tetrahydrofuran / 5 h / 20 °C

6.1: 87 percent / I₂; imidazole; PPh₃ / diethyl ether; acetonitrile / 12 h / 20 °C

7.1: MeLi / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

7.2: diethyl ether; tetrahydrofuran / 3.5 h / -78 - 20 °C

7.3: 75 percent / TBAF*3H₂O / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

8.1: NaBH₄ / ethanol / 18 h / 20 °C

9.1: PPTS / methanol / 48 h / 20 °C

10.1: TPAP; NMO / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; ammonia; methyllithium; iodine; sodium; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetonitrile; 1.1: Oxidation / 1.2: Reduction / 2.1: Grignard reaction / 3.1: Substitution / 4.1: Cyclization / 5.1: Hydrolysis / 6.1: Substitution / 7.1: Metallation / 7.2: Substitution / 7.3: Elimination / 8.1: Reduction / 9.1: Ring cleavage / 10.1: Oxidation;

DOI:10.1002/(SICI)1521-3765(19991001)5:10<2885::AID-CHEM2885>3.0.CO;2-8

Reference yield:

(3R,5RS)-3,7-Dimethyl-1,3,5-octanetriol-3,5-p-methoxybenzylidenacetal (247256-61-7) → athanagrandione (55626-95-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 87 percent / I₂; imidazole; PPh₃ / diethyl ether; acetonitrile / 12 h / 20 °C

2.1: MeLi / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

2.2: diethyl ether; tetrahydrofuran / 3.5 h / -78 - 20 °C

2.3: 75 percent / TBAF*3H₂O / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

3.1: NaBH₄ / ethanol / 18 h / 20 °C

4.1: PPTS / methanol / 48 h / 20 °C

5.1: TPAP; NMO / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methyllithium; iodine; pyridinium p-toluenesulfonate; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetonitrile; 1.1: Substitution / 2.1: Metallation / 2.2: Substitution / 2.3: Elimination / 3.1: Reduction / 4.1: Ring cleavage / 5.1: Oxidation;

DOI:10.1002/(SICI)1521-3765(19991001)5:10<2885::AID-CHEM2885>3.0.CO;2-8

upstream raw materials:

4-hydroxydehydromyoporone

(R)-1-Furan-3-yl-4,8-dimethyl-nonane-1,4,6-triol

(3S,1'S,2'S)-1-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)hex-5-en

(3R,5RS)-3,7-Dimethyl-1,3,5-octanetriol-3,5-p-methoxybenzylidenacetal

Refernces

• 1、 Dimitriadis, Eugene,Massy-Westropp, Ralph A.. "THE CONFIGURATION OF THE SESQUITERPENOID 4-HYDROXY-MYOPORONE (ATHANAGRANDIONE)". . p. 1325 - 1326. Retrieved 2007/10/02.