176706-98-2

Basic information

• Product Name: 2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane
• Synonyms: 2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane;2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane,99%e.e.;2,2'-Isopropylidenebis[(4S)-4-benzyl-2-oxazoline];2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane, 98%, (99% ee)
• CAS NO: 176706-98-2
• Molecular Formula: C₂₃H₂₆N₂O₂
• Molecular Weight: 362.46474
• Mol File: 176706-98-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 483.2±28.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.63±0.70(Predicted)
• CAS DataBase Reference: 2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane(176706-98-2)
• EPA Substance Registry System: 2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane(176706-98-2)

Safety Data

• Hazardous Substances Data: 176706-98-2(Hazardous Substances Data)

Usage

General Description

2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane is a chiral compound commonly used as a chelating ligand in asymmetric catalysis. Its chemical structure consists of two oxazoline rings attached to a central propane backbone, with each oxazoline ring containing a benzyl group. 2,2-Bis[(4S)-4-benzyl-2-oxazolin-2-yl]propane is often employed in the synthesis of various pharmaceuticals and agrochemicals due to its ability to form stable complexes with transition metals, which can catalyze a wide range of chemical reactions with high enantioselectivity. Additionally, it has been found to be effective in promoting a variety of transformations in organic synthesis, making it a valuable tool in the field of asymmetric catalysis.

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Relevant articles and documents

SYNTHESIS OF SMALL MOLECULES INSPIRED BY PHOMOXANTHONE A

Methods, compositions, and kits are provided for synthesizing bioactive chromane, the method including: constructing a tertiary ether stereocenter enantioselectively by catalyzed alkynylation of a substituted chromenone to obtain a chromanone; reducing alkyne and ketone in the chromanone to obtain a chroman; and converting ester to methyl group thereby obtaining chromane.

Cobalt-bisoxazoline-catalyzed asymmetric kumada cross-coupling of racemic α-bromo esters with aryl grignard reagents

The first cobalt-catalyzed asymmetric Kumada cross-coupling with high enantioselectivity has been developed. The reaction affords a unique strategy for the enantioselective arylation of α-bromo esters catalyzed by a cobalt-bisoxazoline complex. A variety of chiral α-arylalkanoic esters were prepared in excellent enantioselectivity and yield (up to 97% ee and 96% yield). The arylated products were transformed into α-arylcarboxylic acids and primary alcohols without erosion of ee. The new enantioenriched α-arylpropionic esters synthesized herein are potentially useful in the development of nonsteroidal anti-inflammatory drugs. This method was conducted on gram-scale and applied to the synthesis of highly enantioenriched (S)-fenoprofen and (S)-ar-turmerone.

Synthesis of non-symmetric bisoxazoline compounds. An easy way to reach tailored chiral ligands

Bisoxazoline compounds have been used as chiral catalyst ligands in a wide variety of reactions. A great deal of effort has been aimed at the synthesis of C2-symmetric bisoxazolines but very few references exist for non-symmetric ones. As part of our studies into the possible usefulness of non-symmetric bisoxazolines, we report an easy method for the synthesis of bisoxazoline compounds bearing different substituents in each oxazoline ring.