Complicatic acid

Base Information

• Chemical Name: Complicatic acid
• CAS No.: 51741-93-6
• Molecular Formula: C15H18O4
• Molecular Weight: 262.3
• DSSTox Substance ID: DTXSID201018791
• Nikkaji Number: J11.217H
• Wikidata: Q104912755
• Mol file: 51741-93-6.mol

Synonyms:Complicatic acid;51741-93-6;DTXSID201018791;Cyclopenta[4,5]pentaleno[1,6a-b]oxirene-5-carboxylic acid, decahydro-3a,5-dimethyl-3-methylene-2-oxo-, [1aS-(1a.alpha.,3a.beta.,3b.alpha.,5.alpha.,6a.alpha.,7aR*)]-

Chemical Property of Complicatic acid

Chemical Property:

• Boiling Point: 440.2±45.0 °C(Predicted)
• PKA: 4.73±0.40(Predicted)
• PSA: 66.90000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 1.79000
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 262.12050905
• Heavy Atom Count: 19
• Complexity: 552

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Complicatic acid

There total 51 articles about Complicatic 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: 40.0%

[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) → (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)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In methanol; water; at -50 - -36 ℃;

DOI:10.1016/S0040-4039(00)85826-8

Reference yield: 40.0%

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-complicatic acid (51741-93-6,55123-34-7,55123-40-5)

Guidance literature:

With dihydrogen peroxide; sodium hydrogencarbonate; In methanol; water; for 1.5h; Ambient temperature;

DOI:10.1021/jo00364a023

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) → (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)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1016/j.tet.2007.03.073

upstream raw materials:

[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

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

Downstream raw materials:

dl-hirsutic acid C

(+)-hirsutic acid