670197
(S)-2-(Methoxydiphenylmethyl)pyrrolidine
95% (HPLC)
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About This Item
Empirical Formula (Hill Notation):
C18H21NO
CAS Number:
Molecular Weight:
267.37
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Assay
95% (HPLC)
optical purity
ee: ≥99.5% (HPLC)
functional group
ether
phenyl
storage temp.
2-8°C
SMILES string
COC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3
InChI
1S/C18H21NO/c1-20-18(17-13-8-14-19-17,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17,19H,8,13-14H2,1H3/t17-/m0/s1
InChI key
CGUGCZSRPDCLBT-KRWDZBQOSA-N
Application
(S)-2-(Methoxydiphenylmethyl)pyrrolidine is a diphenylprolinol methyl ether, which can be used as a catalyst to synthesize:
- Enantioselective ketones via intermolecular asymmetric Michael addition of aldehydes to nonactivated enones.
- Stereoselective chiral bipyrazolidin-3-one derivatives by dipolar cycloaddition reaction of azomethine imines with α, β-unsaturated aldehydes.
- Enantioenriched spiro nitrogen heterocycles via asymmetric nucleophilic epoxidation of α-ylideneoxindole esters.
- Optically active secondary alcohols by asymmetric addition of Et2Zn to various aldehydes.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Signal Word
Warning
Hazard Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Noncovalent organocatalysis: A powerful tool for the nucleophilic epoxidation of α-ylideneoxindoles
Palumbo C, et al.
Organic Letters, 13(23), 6248-6251 (2011)
Diphenylprolinol methyl ether: a highly enantioselective catalyst for Michael addition of aldehydes to simple enones
Chi Y and Gellman SH
Organic Letters, 7(19), 4253-4256 (2005)
Organocatalytic and Stereoselective [3+ 2] Cycloadditions of Azomethine Imines with , α, β-Unsaturated Aldehydes
Chen W, et al.
advanced synthesis and catalysis, 348(14), 1818-1822 (2006)
Chiral pyrrolidine derivatives as catalysts in the enantioselective addition of diethylzinc to aldehydes
Yang X, et al.
Tetrahedron Asymmetry, 10(1), 133-138 (1999)
Organocatalytic and Stereoselective [3+ 2] Cycloadditions of Azomethine Imines with , α, β-Unsaturated Aldehydes
Chen W, et al.
Advanced Synthesis & Catalysis, 348(14), 1818-1822 (2006)
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