Paeonilactone A

Base Information

• Chemical Name: Paeonilactone A
• CAS No.: 98751-79-2
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• UNII: LQV4N956WD
• Nikkaji Number: J181.248C
• Wikidata: Q27155056
• Mol file: 98751-79-2.mol

Synonyms:paeonilactone A;paeonilactone-A

Chemical Property of Paeonilactone A

Chemical Property:

• PSA: 63.60000
• LogP: 0.27800
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 198.08920892
• Heavy Atom Count: 14
• Complexity: 299

Purity/Quality:

98%Min ^*data from raw suppliers

PaeonilactoneA 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC(=O)C(CC2OC1=O)(C)O
• Isomeric SMILES: C[C@@H]1[C@H]2CC(=O)[C@@](C[C@H]2OC1=O)(C)O

Technology Process of Paeonilactone A

There total 35 articles about Paeonilactone A 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: 60.0%

(3R,3aR,5R,6S,7aR)-5,6-dihydroxy-3,6-dimethylhexahydrobenzofuran-2-one (124618-15-1) → paeonilactone A (98751-79-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -50 ℃;

DOI:10.1248/cpb.37.843

Reference yield:

(1R,2R,4S,6S)-(-)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol (24120-79-4) → paeonilactone A (98751-79-2)

Guidance literature:

Multi-step reaction with 13 steps

1: NaBH₄ / ethanol

2: p-TsOH*2H₂O / acetone / Heating

3: mCPBA / CH₂Cl₂ / 0 °C

4: pyridine / benzene / Heating

5: 69 percent / diethylaluminum 2,2,6,6-tetramethylpiperidide / benzene / 0 °C

6: MnO₂ / CH₂Cl₂

7: NaClO₂, NaHPO₄, 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol

8: I₂, KI, sat. NaHCO₃

9: 80 percent / n-Bu₃SnH / AIBN / tetrahydrofuran / Heating

10: 100 percent / H₂ / 10percent Pd/C / ethanol

11: 93 percent / NaOMe / methanol

12: 10percent HCl / tetrahydrofuran

13: SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

With pyridine; hydrogenchloride; manganese(IV) oxide; sodium chlorite; sodium tetrahydroborate; 2-methyl-but-2-ene; diethyl(2,2,6,6-tetramethylpiperidino)aluminium; pyridine-SO₃ complex; hydrogen; iodine; tri-n-butyl-tin hydride; sodium methylate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(00)74124-4

Reference yield:

2-((3aR,5S,7aS)-2,2,7a-Trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-propenal → paeonilactone A (98751-79-2)

Guidance literature:

Multi-step reaction with 7 steps

1: NaClO₂, NaHPO₄, 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol

2: I₂, KI, sat. NaHCO₃

3: 80 percent / n-Bu₃SnH / AIBN / tetrahydrofuran / Heating

4: 100 percent / H₂ / 10percent Pd/C / ethanol

5: 93 percent / NaOMe / methanol

6: 10percent HCl / tetrahydrofuran

7: SO₃*pyridine, Et₃N, DMSO / CH₂Cl₂

With hydrogenchloride; sodium chlorite; 2-methyl-but-2-ene; pyridine-SO₃ complex; hydrogen; iodine; tri-n-butyl-tin hydride; sodium methylate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; potassium iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)74124-4

upstream raw materials:

(3S,3aS,5S,6R,7aS)-5,6-Dihydroxy-3,6-dimethyl-hexahydro-benzofuran-2-one

2-<(1RS)-4-methylcyclohex-3-enyl>acetic acid

(1R,5R)-8-Methyl-2-oxa-bicyclo[3.3.1]non-7-en-3-one

((1S,5S)-5-Hydroxy-4-methyl-cyclohex-3-enyl)-acetic acid methyl ester

Refernces

• 1、 Richardson, David P.,Smith, Thomas E.,Lin, William W.,Kiser, Cynthia N.,Mahon, Brian R.. "STEREOSELECTIVE SYNTHESIS OF THE PAEONILACTONES A, B AND C". . p. 5973 - 5976. Retrieved 2007/10/02.