Hirsutic acid C

Base Information

• Chemical Name: Hirsutic acid C
• CAS No.: 3650-17-7
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• UNII: 81WU46AI9A
• DSSTox Substance ID: DTXSID90190000
• Nikkaji Number: J8.195G
• Wikidata: Q27106871
• Metabolomics Workbench ID: 144025
• Mol file: 3650-17-7.mol

Synonyms:hirsutic acid C

Chemical Property of Hirsutic acid C

Chemical Property:

• Vapor Pressure: 1.31E-09mmHg at 25°C
• Melting Point: 179-182°
• Boiling Point: 440.5°Cat760mmHg
• Flash Point: 166.5°C
• PSA: 70.06000
• Density: 1.33g/cm³
• LogP: 1.58180
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 514

Purity/Quality:

HIRSUTIC ACID C 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2CC34C(O3)C(C(=C)C4(C2C1)C)O)C(=O)O
• Isomeric SMILES: C[C@@]1(C[C@@H]2C[C@]34[C@H](O3)[C@@H](C(=C)[C@]4([C@@H]2C1)C)O)C(=O)O

Technology Process of Hirsutic acid C

There total 27 articles about Hirsutic acid 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: 74.0%

(1S,2R,4S,6R,8S,9S)-8,9-epoxy-1,4-dimethyl-11-methylene-10-oxotricyclo<6.3.0.02,6>undecane-4-carboxylic acid (51741-93-6) → (+)-hirsutic acid (3650-17-7,1403-73-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.166667h;

DOI:10.1248/cpb.38.3230

Reference yield:

methyl (2S,3aR,3bS,7aS)-2,3,3a,3b,4,5,7,7a-octahydro-2,3b-dimethyl-5-oxo-1H-cyclopentapentalene-2-carboxylate (85799-03-7) → (+)-hirsutic acid (3650-17-7,1403-73-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 91 mg / tetrahydrofuran / -78 - 18 °C

2.1: diethyl ether; CH₂Cl₂ / 16 h / 18 °C

3.1: 179 mg / Al₂O₃ / CH₂Cl₂ / 0.5 h / 18 °C

4.1: 69 mg / LiI / dimethylformamide / 34 h / Heating

5.1: 35 percent / H₂O₂; NaOH / methanol; H₂O / 0.75 h / -50 - -36 °C

6.1: 12 mg / NaBH₄ / ethanol; H₂O / 4 h / -35 °C

With aluminum oxide; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; lithium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.03.073

Reference yield:

[2S-(2α,3aα,3bβ,7aα)]-2,3,3a,3b,4,5,7,7a-octahydro-2,3b-dimethyl-4-methylene-5-oxo-1H-cyclopenta[a]pentalene-2-carboxylic acid (85799-05-9) → (+)-hirsutic acid (3650-17-7,1403-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / H₂O₂; NaOH / methanol; H₂O / 0.75 h / -50 - -36 °C

2: 12 mg / NaBH₄ / ethanol; H₂O / 4 h / -35 °C

With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; In methanol; ethanol; water;

DOI:10.1016/j.tet.2007.03.073

upstream raw materials:

(1S,2R,4S,6R,8S,9S)-8,9-epoxy-1,4-dimethyl-11-methylene-10-oxotricyclo<6.3.0.0^2,6>undecane-4-carboxylic acid

methyl (1R,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate

methyl (1S,2aR,2bR,2cR,4S,5aR,5bS,5cS)-1-(benzoyloxy)-decahydro-4,5b-dimethyl-2-oxo-1H-cyclopenta[a]cyclopropa[cd]pentalene-4-carboxylate

methyl [2S-(2α,3aα,3bβ,7aα)]-2,3,3a,3b,4,5,7,7a-octahydro-2,3b-dimethyl-4-[(dimethylamino)methyl]-5-oxo-1H-cyclopenta[a]pentalene-2-carboxylate

Refernces

A total synthesis of (+)-hirsutic acid

10.1248/cpb.38.3230

The research presents the first asymmetric total synthesis of (+)-hirsutic acid in a highly stereocontrolled manner. The synthesis includes a novel method for the preparation of (1S,5R,6S)-6-hydroxy-cis-bicyclo[3.3.0]octan-3-one and a stereospecific Simmons-Smith reaction controlled by the participation of a relatively remote hydroxyl group. Key chemicals involved in the research include methyl (1R,5R)-5-phenoxythiocarbonyl-2-cyclopentenylacetate, (S)-2-cyclopentenylacetic acid, methyl (S)-3-oxo-4-(2-cyclopentenyl)butyrate, and various reagents such as tributyltin hydride, thionyl chloride, Meldrum's acid, and pyridine. The synthesis process involves multiple steps, including reduction, hydrolysis, esterification, and oxidation, with careful control of reaction conditions to achieve the desired stereochemistry and yield of the final product, (+)-hirsutic acid.