Anisomelic acid

Base Information

• Chemical Name: Anisomelic acid
• CAS No.: 59632-76-7
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424
• NSC Number: 272354
• DSSTox Substance ID: DTXSID20418461
• Mol file: 59632-76-7.mol

Synonyms:anisomelic acid

Chemical Property of Anisomelic acid

Chemical Property:

• Vapor Pressure: 2.97E-13mmHg at 25°C
• Refractive Index: 1.544
• Boiling Point: 543.5oC at 760 mmHg
• Flash Point: 191.7oC
• PSA: 63.60000
• Density: 1.12g/cm3
• LogP: 4.34200
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 330.18310931
• Heavy Atom Count: 24
• Complexity: 622

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CCCC(=CCCC(=CC2C(CC1)C(=C)C(=O)O2)C)C(=O)O
• Isomeric SMILES: C/C/1=C\CC/C(=C/CC/C(=C\C2C(CC1)C(=C)C(=O)O2)/C)/C(=O)O

Technology Process of Anisomelic acid

There total 37 articles about Anisomelic 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: 90.0%

(+/-)-methyl anisomelate (80994-13-4,81027-47-6,111057-44-4) → (+/-)-anisomelic acid (59632-76-7,81026-38-2,81026-39-3,93059-31-5,141271-49-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 3h; Heating;

DOI:10.1016/S0040-4020(01)87668-7

Reference yield:

(E)-6-acetoxy-4-methyl-4-hexenal (35334-60-2) → (+/-)-anisomelic acid (59632-76-7,81026-38-2,81026-39-3,93059-31-5,141271-49-0)

Guidance literature:

Multi-step reaction with 18 steps

1: NaBH₄

2: DMAP

3: K₂CO₃ / methanol

4: MnO₂ / (COCl)2, DMSO and Et₃N

5: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h

6: LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C / Heating

7: PPTS / CH₂Cl₂ / 0.08 h / Ambient temperature

8: 1.) B₂H₆, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H₂O₂ / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min.

9: 90 percent / triphenylphosphine, imidazole, I₂ / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C

10: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight

11: MeOH / PPTS / 0.08 h / Heating

12: 1.) DMSO, (COCl)2 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min; 2.) CH₂Cl₂, -78 to 0 deg C

13: 35 percent / K₂CO₃, 18-crown-6 / toluene / 80 °C

14: H₂O / PPTS / tetrahydrofuran / 1.5 h / Heating

15: PCC, sodium acetate / CH₂Cl₂ / 2.5 h

16: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min.

17: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C

18: 90 percent / KOH / aq. ethanol / 3 h / Heating

With 1H-imidazole; triisopropoxytitanium(IV) chloride; methanol; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; 1,10-Phenanthroline; 2-methyl-but-2-ene; oxalyl dichloride; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; water; dihydrogen peroxide; iodine; sodium acetate; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; pyridinium chlorochromate; diborane; lithium diisopropyl amide; pyridinium p-toluenesulfonate; copper(II) iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)87668-7

Reference yield:

(2E,6E)-6-methylnona-2,6,8-trien-1-ol (110965-88-3) → (+/-)-anisomelic acid (59632-76-7,81026-38-2,81026-39-3,93059-31-5,141271-49-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) sodium hydride / 1.) DME, RT, 10 min; 2.) DME, RT, overnight

2: 1.) TMEDA, n-BuLi 2.) ClTi(O-iPr)3 / 1.) ether, hexane, -78 deg C, 1 h 2.) ether, hexane, -78 deg C, 2 h then -10 deg C, 1.5 h

3: LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C / Heating

4: PPTS / CH₂Cl₂ / 0.08 h / Ambient temperature

5: 1.) B₂H₆, 2-methyl-2-butene 3.) 3M NaOH, 30percent aq. H₂O₂ / 1.) THF, -10 deg C, 2 h 2.) THF, 0 deg C, 30 min; 3.) THF, RT, 30 min.

6: 90 percent / triphenylphosphine, imidazole, I₂ / tetrahydrofuran; acetonitrile / 0.5 h / -10 °C

7: 1.) NaH / 1.) DMSO, RT, 30 min; 2.) DMSO, overnight

8: MeOH / PPTS / 0.08 h / Heating

9: 1.) DMSO, (COCl)2 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min; 2.) CH₂Cl₂, -78 to 0 deg C

10: 35 percent / K₂CO₃, 18-crown-6 / toluene / 80 °C

11: H₂O / PPTS / tetrahydrofuran / 1.5 h / Heating

12: PCC, sodium acetate / CH₂Cl₂ / 2.5 h

13: 1.) LDA, 1,10-phenanthroline / 1.) THF, -78 deg C, 15 min; 2.) THF, -20 deg C, 5 min.

14: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulphonate / copper(II) iodide / acetonitrile / 4 h / 55 - 58 °C

15: 90 percent / KOH / aq. ethanol / 3 h / Heating

With 1H-imidazole; triisopropoxytitanium(IV) chloride; methanol; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 1,10-Phenanthroline; 2-methyl-but-2-ene; oxalyl dichloride; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; water; dihydrogen peroxide; iodine; sodium acetate; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; pyridinium chlorochromate; diborane; lithium diisopropyl amide; pyridinium p-toluenesulfonate; copper(II) iodide; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)87668-7

upstream raw materials:

(+/-)-methyl anisomelate

(E)-6-acetoxy-4-methyl-4-hexenal

(2E,6E)-6-methylnona-2,6,8-trien-1-ol

<(2E)-6-Hydroxy-3-methyl-2-hexenyl>acetat

Downstream raw materials:

(rel-3Ξ,3aR)-(6E,10Z,14E)-6,14-dimethyl-2-oxo-(3ar,15at)-3a,4,5,8,9,12,13,15a-octahydro-spiro[cyclotetradeca[b]furan-3,3'-pyrazole]-10-carboxylic acid methyl ester

Refernces

• 1、 Marshall, James A.,DeHoff, Bradley S.. "STEREOSELECTIVE TOTAL SYNTHESIS OF THE CEMBRANOLIDE DITERPENE ANISOMELIC ACID". . p. 4873 - 4876. Retrieved 2007/10/02.