2,6-bis({[(2S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]methyl})-4-methylphenol

• ChemBase ID: 140735
• Molecular Formular: C43H46N2O3
• Molecular Mass: 638.83694
• Monoisotopic Mass: 638.35084334
• SMILES: Cc1cc(c(c(c1)CN1CCC[C@H]1C(c1ccccc1)(c1ccccc1)O)O)CN1CCC[C@H]1C(c1ccccc1)(c1ccccc1)O
• Canonical SMILES: Cc1cc(CN2CCC[C@H]2C(c2ccccc2)(c2ccccc2)O)c(c(c1)CN1CCC[C@H]1C(c1ccccc1)(c1ccccc1)O)O
• InChI: InChI=1S/C43H46N2O3/c1-32-28-33(30-44-26-14-24-39(44)42(47,35-16-6-2-7-17-35)36-18-8-3-9-19-36)41(46)34(29-32)31-45-27-15-25-40(45)43(48,37-20-10-4-11-21-37)38-22-12-5-13-23-38/h2-13,16-23,28-29,39-40,46-48H,14-15,24-27,30-31H2,1H3/t39-,40-/m0/s1
• InChIKey: NEOVWBNAXIBNRT-ZAQUEYBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-bis({[(2S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]methyl})-4-methylphenol
• IUPAC Traditional name: 2,6-bis({[(2S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]methyl})-4-methylphenol
• Synonyms: Trost (S,S)-Bis-ProPhenol Ligand; (S,S)-2,6-Bis[2-(hydroxydiphenylmethyl)pyrrolidin-1-ylmethyl]-4-methylphenol; (S,S)-(+)-2,6-Bis[2-(hydroxydiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenol; (S,S)-2,6-双[2-(羟基二苯甲基)吡咯烷-1-基甲基]-4-甲基苯酚; (S,S)-(+)-2,6-双[2-(羟基二苯甲基)-1-吡咯烷基-甲基]-4-甲基苯酚

Database IDs

• MDL Number: MFCD08276890
• PubChem SID: 24884980; 162234975
• PubChem CID: 11308810

CALCULATED PROPERTIES

• Acid pKa: 7.4945493
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.5668249
• LogD (pH = 7.4): 3.5263677
• Log P: 6.5067267
• Molar Refractivity: 195.1445 cm^3
• Polarizability: 76.076 Å^3
• Polar Surface Area: 67.17 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 93-102 °C
• Optical Rotation: [α]/D +50°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 21/22-36/38-40
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302 + H312-H315-H319-H351
• GHS Precautionary statements: P280-P305 + P351 + P338
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 95%
• Impurities: ≤6% dichloromethane and/or diethylether
• Empirical Formula (Hill Notation): C43H46N2O3

DETAILS

Sigma Aldrich - 668370

Application
A useful catalyst in asymmetric aldol, Henry, and Mannich-type reactions.1
Packaging
1, 5 g in glass bottle