Conocarpan

Base Information

• Chemical Name: Conocarpan
• CAS No.: 56319-02-9
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.34
• European Community (EC) Number: 803-862-3
• NSC Number: 727405
• DSSTox Substance ID: DTXSID70451404
• Nikkaji Number: J1.653.628H,J14.818K
• Wikidata: Q76416414
• Metabolomics Workbench ID: 126954
• ChEMBL ID: CHEMBL2147421
• Mol file: 56319-02-9.mol

Synonyms:conocarpan

Chemical Property of Conocarpan

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 266.130679813
• Heavy Atom Count: 20
• Complexity: 343

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=CC2=C(C=C1)OC(C2C)C3=CC=C(C=C3)O
• Isomeric SMILES: C/C=C/C1=CC2=C(C=C1)O[C@H]([C@@H]2C)C3=CC=C(C=C3)O

Technology Process of Conocarpan

There total 14 articles about Conocarpan 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: 95.0%

toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester (944249-92-7) → 4-{(2R,3R)-3-methyl-5-[(E)prop-1-en-1-yl]-2,3-dihydrobenzofuran-2-yl}phenol (56319-02-9,118201-52-8,221666-27-9)

Guidance literature:

With sodium-mercury amalgam (10%); water; In methanol; optical yield given as %ee; Inert atmosphere;

DOI:10.1039/b801858h

Reference yield:

toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-1-propenylbenzofuran-2-yl)]phenyl ester → 4-{(2R,3R)-3-methyl-5-[(E)prop-1-en-1-yl]-2,3-dihydrobenzofuran-2-yl}phenol (56319-02-9,118201-52-8,221666-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / PdCl₂(PhCN)2 / CH₂Cl₂ / 240 h

2: Na(Hg) / methanol; H₂O / 12 h

With sodium amalgam; bis(benzonitrile)palladium(II) dichloride; In methanol; dichloromethane; water;

DOI:10.1039/b704211f

Reference yield:

toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester (944249-85-8) → 4-{(2R,3R)-3-methyl-5-[(E)prop-1-en-1-yl]-2,3-dihydrobenzofuran-2-yl}phenol (56319-02-9,118201-52-8,221666-27-9)

Guidance literature:

Multi-step reaction with 7 steps

1: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -25 °C

2: 64 percent / aq. NaOH / 2.5 h / 70 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

4: 71 percent / NaI / butan-2-one / 4 h / Heating

5: 69 percent / Bu₃SnH; AIBN / toluene / 2 h / 80 °C

6: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C

7: Na(Hg) / methanol; H₂O / 12 h

With tert.-butylhydroperoxide; sodium hydroxide; sodium amalgam; (-)-diisopropyl tartrate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tert.-butyl lithium; tri-n-butyl-tin hydride; triethylamine; sodium iodide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; water; toluene; butanone; 1: Sharpless asymmetric epoxidation / 6: Wittig reaction;

DOI:10.1039/b704211f

upstream raw materials:

toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester

toluene-4-sulfonic acid 4-[(R)-1-(4-formyl-2-iodophenoxy)allyl]phenyl ester

toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

(2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester

Downstream raw materials:

C₃₆H₃₆O₄

C₃₆H₃₆O₄

(2S')-4-<2'-(2-hydroxy-5-propylphenyl)propyl>phenol

Refernces

Enantioselective Oxy-Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (?)-Conocarpan

10.1002/adsc.201701278

The research focuses on the development of an enantioselective oxy-Heck-Matsuda arylation reaction to synthesize chiral dihydrobenzofuran systems, which are important structural motifs in natural products with biological activity. The study utilizes a variety of styrenic olefins and aryldiazonium salts as reactants, with a pyrimidinebisoxazoline (PyriBox) ligand and a palladium catalyst to achieve moderate to good yields and high trans diastereoselectivity (up to 20:1) with enantioselectivities up to 90:10. The methodology is demonstrated through the concise total synthesis of the neolignan (?)-conocarpan, and the absolute stereochemistry of the products is confirmed via X-ray diffraction analysis of a brominated intermediate. The experiments involve mild reaction conditions, low catalyst loading, and various analyses, including NMR, HPLC, and X-ray crystallography, to characterize the products and assess the stereochemical outcomes.