dl-hirsutic acid C

Base Information

• Chemical Name: dl-hirsutic acid C
• CAS No.: 55123-33-6
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 55123-33-6.mol

Synonyms:

Chemical Property of dl-hirsutic acid C

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dl-hirsutic acid C

There total 27 articles about dl-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:

dl-complicatic acid (51741-93-6,55123-34-7,55123-40-5) → dl-hirsutic acid C (55123-33-6,1403-73-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -35 - 0 ℃; for 0.583333h;

DOI:10.1021/ja00346a054

Reference yield:

4α-carboxy-1β,4β-dimethyl-11-methylene-(2α,6α)-tricyclo<6.3.0.02,6>undec-8-en-10-one (55093-82-8,55123-39-2,60828-59-3,85799-05-9) → dl-hirsutic acid C (55123-33-6,1403-73-2)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; Yield given. Multistep reaction; 1.) EtOH, H₂O;

DOI:10.1021/jo00364a023

Reference yield:

3-cyclopentene-1-carboxylic acid (7686-77-3) → dl-hirsutic acid C (55123-33-6,1403-73-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 84 percent / conc. H₂SO₄ / diethyl ether / 96 h / Ambient temperature

2: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C (5 min), -10 deg C (10 min); 2) THF, hexane, -78 deg C --> room temperature

3: 50 percent / zinc-copper couple, phosphorus oxychloride / diethyl ether / 3 h

4: 1.) Li(CH₃)2Cu / 1) THF, ether, -78 --> -50 deg C, 30 min; 2) HMPA, -78 deg C

5: diethyl ether; methanol / 82 h / -35 °C

6: 2.50 g / sodium borohydride / methanol / 0.17 h / 0 °C

7: 0.740 g / aq. Cr(ClO₄)2, NH₂CH₂CH₂NH₂ / dimethylformamide / 1.5 h

8: Zn-Cu, phosphorus oxychloride / diethyl ether / 1) 28 deg C, 4.5 h; 2) 17 deg C, overnight

9: diethyl ether; methanol / 0.5 h / Ambient temperature

10: 0.510 g / Zn, glacial acetic acid / 4.5 h / 85 °C

11: 58 percent Turnov_. / palladium(II) chloride, palladium(II) acetate, oxygen / dioxane; H₂O / 5 h / 85 °C

12: 99 percent / AlBr₃ / tetrahydrothiophene / 69 h

13: 1.) lithium bis(trimethylsilyl)amide / 1) THF, -78 --> -35 deg C; 2) THF, -35 deg C --> room temperature

14: 40 mg / aq. formalin, potassium carbonate / acetone

15: aq. H₂O₂, aq. sodium hydroxide / ethanol / 4 h / -35 °C

16: 18 mg / sodium borohydride / ethanol / 0.58 h / -35 - 0 °C

With sodium hydroxide; sodium tetrahydroborate; formaldehyd; aluminum tri-bromide; zinc copper; chromium(II) perchlorate; sulfuric acid; lithium dimethylcuprate; dihydrogen peroxide; oxygen; palladium diacetate; copper; potassium carbonate; acetic acid; ethylenediamine; palladium dichloride; lithium hexamethyldisilazane; zinc; lithium diisopropyl amide; trichlorophosphate; In thiophene; 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja00346a054

upstream raw materials:

4α-carboxy-1β,4β-dimethyl-11-methylene-(2α,6α)-tricyclo<6.3.0.0^2,6>undec-8-en-10-one

dl-complicatic acid

3-cyclopentene-1-carboxylic acid

methyl (2R*,3aS*,3bR*,7aR*)-2,3,3a,3b,4,5,7,7a-octahydro-2,3b-dimethyl-5-oxo-1H-cyclopentapentalene-2-carboxylate