2-[(5S,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid

Base Information

• Chemical Name: 2-[(5S,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid
• CAS No.: 115473-63-7
• Molecular Formula: C15H20 O3
• Molecular Weight: 248.3175
• DSSTox Substance ID: DTXSID90151111
• Mol file: 115473-63-7.mol

Synonyms:rupestonic acid

Chemical Property of 2-[(5S,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid

Chemical Property:

• Vapor Pressure: 6.76E-09mmHg at 25°C
• Boiling Point: 438°Cat760mmHg
• Flash Point: 232.8°C
• PSA: 54.37000
• Density: 1.12g/cm³
• LogP: 2.96890
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 445

Purity/Quality:

≥98% ^*data from raw suppliers

Rupestonicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(CC2=C(C(=O)CC12)C)C(=C)C(=O)O
• Isomeric SMILES: C[C@H]1CC[C@@H](CC2=C(C(=O)C[C@@H]12)C)C(=C)C(=O)O

Technology Process of 2-[(5S,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid

There total 32 articles about 2-[(5S,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid 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:

C15H22O2 → (5S,8S,8aS)-2-(3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylic acid (115473-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: chromium(VI) oxide; 3,5-dimethyl-1H-pyrazole / dichloromethane / 0.83 h / 0 °C

2: 2-methyl-but-2-ene; potassium dihydrogenphosphate; sodium chlorite / water; acetone / 3 h

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In dichloromethane; water; acetone;

DOI:10.1021/acs.orglett.7b03459

Reference yield:

C15H20O2 → (5S,8S,8aS)-2-(3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylic acid (115473-63-7)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In water; acetone; for 3h;

DOI:10.1021/acs.orglett.7b03459

Reference yield:

C14H30O2Si → (5S,8S,8aS)-2-(3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylic acid (115473-63-7)

Guidance literature:

Multi-step reaction with 24 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 18 h / 0 °C

2.1: 4-methylmorpholine N-oxide; potassium osmate(VI) dihydrate / water; tert-butyl alcohol / 16 h / 20 °C

3.1: NaIO₄ supported on silica gel / dichloromethane / 0.33 h

4.1: tetrahydrofuran / 0.17 h / -15 °C

5.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 24 h

6.1: palladium 10% on activated carbon; palladium(II) hydroxide; hydrogen / methanol / 5 h

7.1: Dess-Martin periodane / dichloromethane / 1 h

8.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / -50 - 20 °C

9.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

10.1: pyridine hydrogenfluoride / 16 h

11.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / acetonitrile / 1 h / Molecular sieve

12.1: tetrahydrofuran; hexane / 3 h / -78 °C

12.2: 3 h

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h

14.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / acetonitrile / 4 h / Molecular sieve

15.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 10 h / 50 °C / Inert atmosphere

16.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h

17.1: potassium tert-butylate / tetrahydrofuran / 3 h

18.1: acetic acid / 12 h

19.1: 1H-imidazole / tetrahydrofuran-d8 / 9 h

20.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / acetonitrile / 1 h / Molecular sieve

21.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

22.1: toluene-4-sulfonic acid / methanol / 0.17 h

23.1: chromium(VI) oxide; 3,5-dimethyl-1H-pyrazole / dichloromethane / 0.83 h / 0 °C

24.1: 2-methyl-but-2-ene; potassium dihydrogenphosphate; sodium chlorite / water; acetone / 3 h

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium osmate(VI) dihydrate; sodium chlorite; potassium dihydrogenphosphate; samarium diiodide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; palladium(II) hydroxide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; tetrahydrofuran-d8; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 21.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.7b03459

upstream raw materials:

(Z)-(-)-methyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

(R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)prop-2-en-1-ol

tert-butyl (R,Z)-2-((3-(2,2-dimethyl-1,3-dioxolan-4-yl)allyl)oxy)acetate

tert-butyl (2S,3S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxypent-4-enoate

Downstream raw materials:

C₂₁H₂₄O₃

C₂₁H₂₂Cl₂O₃

C₂₁H₂₄O₄

C₂₃H₂₆O₅