Isoboonein acetate

Base Information

• Chemical Name: Isoboonein acetate
• CAS No.: 99891-77-7
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.246
• Mol file: 99891-77-7.mol

Synonyms:Isoboonein acetate;Reaxys ID: 6504764;(4aR,6S,7R,7aS)-6-(Acetyloxy)hexahydro-7-methylcyclopenta[c]pyran-3(1H)-one;Cyclopenta[c]pyran-3(1H)-one, 6-(acetyloxy)hexahydro-7-methyl-, (4aR,6S,7R,7aS)-

Chemical Property of Isoboonein acetate

Chemical Property:

• Boiling Point: 336.4±35.0 °C(Predicted)
• PSA: 52.60000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 1.13720

Purity/Quality:

98% ^*data from raw suppliers

Isobooneinacetate ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Isoboonein acetate

There total 14 articles about Isoboonein acetate 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:

(+)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene (78037-77-1,448922-61-0) → Acetic acid (4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydro-cyclopenta[c]pyran-6-yl ester (99891-77-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / MCPBA

2: 89 percent

3: 89 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

4: 86 percent / HgCl₂, Al / tetrahydrofuran; ethanol

5: 82 percent / MCPBA / CH₂Cl₂ / 72 h / Ambient temperature

6: 79 percent / pyridinium chlorochromate/alumina / CH₂Cl₂ / 6 h

7: 65 percent / aq. TFA / CH₂Cl₂ / 12 h / Ambient temperature

8: 1.) H₂, 2.) pyridinium p-toluenesulfonate / 1.) 5 percent Pd/C / 1.) EtOAc, 72 h, 2.) C₆H₆, reflux, 5 h

9: 78 percent / NaBH₄ / propan-2-ol / 0.17 h / 0 °C

10: Ph₃P, (NCO₂C₂H₅)2 / tetrahydrofuran / 24 h / Ambient temperature

With aluminum oxide; sodium tetrahydroborate; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; aluminium; trifluoroacetic acid; mercury dichloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1248/cpb.46.1451

Reference yield:

4aR,7aS-tetrahydro-6-oxo-7-methylenecyclopentapyran-3(1H)-one (214895-68-8) → Acetic acid (4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydro-cyclopenta[c]pyran-6-yl ester (99891-77-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) H₂, 2.) pyridinium p-toluenesulfonate / 1.) 5 percent Pd/C / 1.) EtOAc, 72 h, 2.) C₆H₆, reflux, 5 h

2: 78 percent / NaBH₄ / propan-2-ol / 0.17 h / 0 °C

3: Ph₃P, (NCO₂C₂H₅)2 / tetrahydrofuran / 24 h / Ambient temperature

With sodium tetrahydroborate; hydrogen; pyridinium p-toluenesulfonate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1248/cpb.46.1451

Reference yield:

4-hydroxymethyl-7-oxatricyclo<3.2.1.13,8>nonan-2-ol (188441-94-3) → Acetic acid (4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydro-cyclopenta[c]pyran-6-yl ester (99891-77-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent

2: 89 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

3: 86 percent / HgCl₂, Al / tetrahydrofuran; ethanol

4: 82 percent / MCPBA / CH₂Cl₂ / 72 h / Ambient temperature

5: 79 percent / pyridinium chlorochromate/alumina / CH₂Cl₂ / 6 h

6: 65 percent / aq. TFA / CH₂Cl₂ / 12 h / Ambient temperature

7: 1.) H₂, 2.) pyridinium p-toluenesulfonate / 1.) 5 percent Pd/C / 1.) EtOAc, 72 h, 2.) C₆H₆, reflux, 5 h

8: 78 percent / NaBH₄ / propan-2-ol / 0.17 h / 0 °C

9: Ph₃P, (NCO₂C₂H₅)2 / tetrahydrofuran / 24 h / Ambient temperature

With aluminum oxide; sodium tetrahydroborate; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; aluminium; trifluoroacetic acid; mercury dichloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1248/cpb.46.1451

upstream raw materials:

acetic anhydride

isoboonein

acetic acid

4aR,6R,7R,7aS-tetrahydro-6-hydroxy-7-methylcyclopentapyran-3(1H)-one

Downstream raw materials:

isoboonein

Refernces

• 1、 Murai, Fujio,Tagawa, Motoko,Matsuda, Satoko,Kikuchi, Tohru,Uesato, Shinichi,et al.. "ABELIOSIDES A AND B, SECOIRIDOID GLUCOSIDES FROM ABELIA GRANDIFLORA". . p. 2329 - 2336. Retrieved 2007/10/02.