Bakkenolide C

Base Information

• Chemical Name: Bakkenolide C
• CAS No.: 18456-00-3
• Molecular Formula: C20H28O5
• Molecular Weight: 348.43332
• Mol file: 18456-00-3.mol

Synonyms:Bakkenolide C;(3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxospiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-4-yl) (E)-2-methylbut-2-enoate;[(2R,3R,3aS,4S,7S,7aR)-3-hydroxy-7,7a-dimethyl-4'-methylidene-2'-oxospiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-4-yl] (Z)-2-methylbut-2-enoate;18456-00-3

Chemical Property of Bakkenolide C

Chemical Property:

• Melting Point: 165 - 165.5 °C (CH2Cl2)
• PSA: 72.83000
• LogP: 2.78080
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 348.19367399
• Heavy Atom Count: 25
• Complexity: 651

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=C(C)C(=O)OC1CCC(C2(C1C(C3(C2)C(=C)COC3=O)O)C)C
• Isomeric SMILES: C/C=C(\C)/C(=O)OC1CCC(C2(C1C(C3(C2)C(=C)COC3=O)O)C)C

Technology Process of Bakkenolide C

There total 22 articles about Bakkenolide C 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: 86.0%

(-)-Bakkenolide III (24909-95-3) + (2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride (137601-32-2) → (-)-Bakkenolide C (18456-00-3)

Guidance literature:

In toluene; Heating;

DOI:10.1002/1521-3773(20001201)39:23<4314::AID-ANIE4314>3.0.CO;2-Q

Reference yield:

(1S,2R,6S,8S)-ethyl-1,2-dimethyl-7-oxobicyclo[4.3.0]nonane-8-carboxylate (192197-73-2) → (-)-Bakkenolide C (18456-00-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: toluene / Heating

2.1: Mn(O₂CCH₃)3 / ethanol / 20 °C

3.1: NaHMDS / tetrahydrofuran / 4 h / -65 °C

3.2: C₆H₅SeBr / tetrahydrofuran / -65 - 0 °C

3.3: 77 percent / aq. H₂O₂; AcOH / 1.5 h / 0 °C

4.1: NaBH₄; CeCl₃ / ethanol / 1.5 h / -30 °C

5.1: 57 percent / vanadyl acetylacetonate; TBHP / toluene; 1,2-dichloro-ethane / 6 h / 50 - 60 °C

6.1: 83 percent / (ClCO)2; DMSO; Et₃N / CH₂Cl₂ / -60 - -20 °C

7.1: 83 percent / SmI₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

8.1: 82 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

9.1: 86 percent / toluene / 32 h / Heating

With tert.-butylhydroperoxide; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; oxalyl dichloride; vanadyl acetylacetonate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; manganese triacetate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; 4.1: Luche reduction;

DOI:10.1021/ja0208456

Reference yield:

(-)-1,10-didehydro-7-epi-9-oxo-bakkenolide A (322479-98-1) → (-)-Bakkenolide C (18456-00-3)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄; CeCl₃ / ethanol / 1.5 h / -30 °C

2: 57 percent / vanadyl acetylacetonate; TBHP / toluene; 1,2-dichloro-ethane / 6 h / 50 - 60 °C

3: 83 percent / (ClCO)2; DMSO; Et₃N / CH₂Cl₂ / -60 - -20 °C

4: 83 percent / SmI₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

5: 82 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

6: 86 percent / toluene / 32 h / Heating

With tert.-butylhydroperoxide; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; oxalyl dichloride; vanadyl acetylacetonate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; 1: Luche reduction;

DOI:10.1021/ja0208456

upstream raw materials:

(-)-Bakkenolide III

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride

(2S,3aR,4S,7aS)-prop-2-ynyl 3a,4-dimethyl-1-oxooctahydro-1H-indene-2-carboxylate

2-methyl-2-cyclohexen-1-one

Downstream raw materials:

bakkenolide B

Refernces

• 1、 Hamelin, Olivier,Wang, Yanyun,Depres, Jean-Pierre,Greene, Andrew E.. "The first entry to complex bakkanes: A highly effective retroaldol-aldol-based approach to (-)-bakkenolides III B, C, and H". . p. 4314 - 4316. Retrieved 2007/10/03.