Longistylin C

Base Information

• Chemical Name: Longistylin C
• CAS No.: 64125-60-6
• Molecular Formula: C20H22 O2
• Molecular Weight: 294.3875
• DSSTox Substance ID: DTXSID201317571
• Nikkaji Number: J1.558.525K
• Metabolomics Workbench ID: 134321
• ChEMBL ID: CHEMBL445702
• Mol file: 64125-60-6.mol

Synonyms:longistyline C

Chemical Property of Longistylin C

Chemical Property:

• Vapor Pressure: 5.41E-09mmHg at 25°C
• Melting Point: 88-91 °C
• Boiling Point: 457.6°Cat760mmHg
• PKA: 9.61±0.25(Predicted)
• Flash Point: 237.2°C
• PSA: 29.46000
• Density: 1.087g/cm³
• LogP: 5.07990
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 294.161979940
• Heavy Atom Count: 22
• Complexity: 375

Purity/Quality:

98% ^*data from raw suppliers

LongistylinC 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=C(C=C1OC)O)C=CC2=CC=CC=C2)C
• Isomeric SMILES: CC(=CCC1=C(C=C(C=C1OC)O)/C=C/C2=CC=CC=C2)C

Technology Process of Longistylin C

There total 8 articles about Longistylin 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: 78.0%

→ 3-methoxy-4-(3-methylbut-2-enyl)-5-[(E)-2-phenylethylene]phenol (64125-60-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; for 2h; Reflux;

Reference yield: 70.0%

(E)-methyl 6-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-2-styrylbenzoate → 3-methoxy-4-(3-methylbut-2-enyl)-5-[(E)-2-phenylethylene]phenol (64125-60-6)

Guidance literature:

With potassium hydroxide; In ethanol; at 110 ℃; for 0.5h; under 2585.81 Torr; Temperature; Pressure; Microwave irradiation;

DOI:10.1021/acs.jmedchem.6b01301

Reference yield:

(E)-2,4-dimethoxy-6-styrylbenzoic acid methyl ester (1258410-99-9) → 3-methoxy-4-(3-methylbut-2-enyl)-5-[(E)-2-phenylethylene]phenol (64125-60-6)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine / methanol / 0 - 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 12 h / 110 °C

3: boron trichloride / dichloromethane / 2 h / -78 - 20 °C

4: potassium hydroxide / ethanol / 0.5 h / 110 °C / 2585.81 Torr / Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; boron trichloride; potassium hydroxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 2: |Stille Cross Coupling;

DOI:10.1021/acs.jmedchem.6b01301

upstream raw materials:

2-methyl-3-buten-2-ol

3-methoxy-5-[(E)-2-phenylvinyl]phenol

(E)-2,4-dimethoxy-6-styrylbenzoic acid methyl ester

benzaldehyde

Refernces

• 1、 -. "CAJANINE STRUCTURE ANALOGOUS COMPOUND, PREPARATION METHOD AND USE". Paragraph 0085; 0244. . Retrieved 2015/01/06.