(R)-Vapol

Base Information

• Chemical Name: (R)-Vapol
• CAS No.: 147702-15-6
• Molecular Formula: C₄₀H₂₆O₂
• Molecular Weight: 538.645
• European Community (EC) Number: 802-806-5
• Nikkaji Number: J2.959.662J,J737.939K,J2.469.576J
• Mol file: 147702-15-6.mol

Synonyms:(R)-VAPOL;147702-16-7;Vapol;(3R)-2,2'-Diphenyl[3,3'-biphenanthrene]-4,4'-diol;(3S)-2,2'-Diphenyl[3,3'-biphenanthrene]-4,4'-diol;3-(4-hydroxy-2-phenylphenanthren-3-yl)-2-phenylphenanthren-4-ol;2,2'-diphenyl-[3,3'-biphenanthrene]-4,4'-diol;200810-26-0;SCHEMBL8008142;(R)-VAPOL, 97%;(S)-VAPOL, 97%;3,3'-Bi(2-phenylphenanthrene-4-ol);(S)-2,2'-Diphenyl-(4-biphenanthrol);BS-51483;CS-0085177;CS-0086433;E70346;J-008397;J-008398;(aR)-2,2'-Diphenyl-3,3'-biphenanthrene-4,4'-diol;(aS)-2,2'-Diphenyl-3,3'-biphenanthrene-4,4'-diol

Chemical Property of (R)-Vapol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 185-191 °C
• Refractive Index: 1.777
• Boiling Point: 712.173 °C at 760 mmHg
• PKA: 8.37±0.30(Predicted)
• Flash Point: 298.408 °C
• PSA: 40.46000
• Density: 1.287 g/cm³
• LogP: 12.13310
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 11.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 538.193280068
• Heavy Atom Count: 42
• Complexity: 816

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3S)-(+)-2,2'-Diphenyl-[3,3'-biphenanthrene]-4,4'-diol dichloromethane adduct, min. 98% (S)-VAPOL ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R37/38-40-41:
• Hazard Codes: Xn
• Statements: 37/38-40-41
• Safety Statements: 26-36/37/39-36/37-24/25-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C(=C3C(=C2)C=CC4=CC=CC=C43)O)C5=C(C=C6C=CC7=CC=CC=C7C6=C5O)C8=CC=CC=C8
• Uses: VAPOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

Technology Process of (R)-Vapol

There total 6 articles about (R)-Vapol 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: 89.0%

2-phenyl-4-phenanthrol (175223-64-0) → rac-2,2'-diphenyl-[3,3'-biphenanthrene]-4,4'-diol (147702-15-6,147702-16-7,200810-26-0)

Guidance literature:

With air; at 190 ℃; for 34h;

DOI:10.1021/ja952018t

Reference yield:

phenylacetylene (536-74-3) → rac-2,2'-diphenyl-[3,3'-biphenanthrene]-4,4'-diol (147702-15-6,147702-16-7,200810-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) Ac₂O, Et₃N, 3.) AlCl₃, EtSH

2: 89 percent / air / 34 h / 190 °C

With aluminium trichloride; air; acetic anhydride; triethylamine; ethanethiol;

DOI:10.1021/ja952018t

Reference yield:

Acetic acid 4-methoxy-2-phenyl-phenanthren-1-yl ester (175223-47-9) → rac-2,2'-diphenyl-[3,3'-biphenanthrene]-4,4'-diol (147702-15-6,147702-16-7,200810-26-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / AlCl₃, EtSH / CH₂Cl₂ / 4.5 h / 25 °C

2: 89 percent / air / 34 h / 190 °C

With aluminium trichloride; air; ethanethiol; In dichloromethane;

DOI:10.1021/ja952018t

upstream raw materials:

2-phenyl-4-phenanthrol

phenylacetylene

Acetic acid 4-methoxy-2-phenyl-phenanthren-1-yl ester

2-naphthylacetyl chloride

Downstream raw materials:

[B₂O((S)-VAPOL^(2-))(phenoxy)2]

[B((S)-VAPOL^(2-))(phenoxy)]

Refernces

• 1、 Bao, Jianming,Wulff, William D.,Dominy, James B.,Fumo, Michael J.,Grant, Eugene B.,Rob, Alexander C.,Whitcomb, Mark C.,Yeung, Siu-Man,Ostrander, Robert L.,Rheingold, Arnold L.. "Synthesis, resolution, and determination of absolute configuration of a vaulted 2,2′-binaphthol and a vaulted 3,3′-biphenanthrol (VAPOL)". . p. 3392 - 3405. Retrieved 2007/10/03.