835652-06-7

Basic information

• Product Name: 1,2-Cyclobutanedicarboxylic acid, 3,4-bis(2-hydroxyphenyl)-, diethyl ester, (1S,2S,3S,4S)-
• CAS NO: 835652-06-7
• Molecular Formula: C22H24O6
• Molecular Weight: 384.429
• Mol File: 835652-06-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-Cyclobutanedicarboxylic acid, 3,4-bis(2-hydroxyphenyl)-, diethyl ester, (1S,2S,3S,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclobutanedicarboxylic acid, 3,4-bis(2-hydroxyphenyl)-, diethyl ester, (1S,2S,3S,4S)-(835652-06-7)
• EPA Substance Registry System: 1,2-Cyclobutanedicarboxylic acid, 3,4-bis(2-hydroxyphenyl)-, diethyl ester, (1S,2S,3S,4S)-(835652-06-7)

Safety Data

• Hazardous Substances Data: 835652-06-7(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 5248-12-4 anti head-to-head coumarin dimer 

Downstream Products

• 5248-12-4 anti head-to-head coumarin dimer 
• 85381-11-9 2-ethoxycarbonyl-1-(2-hydroxyphenyl)-1α,2α,2aβ,8bβ-tetrahydro-3H-cyclobutachromen-3-one 
• 835652-17-0 (1S,2S,3S,4S)-3,4-Bis-{2-[bis-(4-tert-butyl-phenyl)-phosphinoyl]-phenyl}-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-25-0 (1S,2S,3S,4S)-3,4-Bis-{2-[bis-(4-tert-butyl-phenyl)-phosphanyl]-phenyl}-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-19-2 (1S,2S,3S,4S)-3,4-Bis-{2-[bis-(3,5-dimethyl-phenyl)-phosphinoyl]-phenyl}-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-34-1 ((1S,2S,3S,4S)-2,3-Bis-{2-[bis-(4-tert-butyl-phenyl)-phosphanyl]-phenyl}-4-hydroxymethyl-cyclobutyl)-methanol 
• 835652-16-9 (1S,2S,3S,4S)-3,4-Bis-{2-[bis-(4-methoxy-phenyl)-phosphinoyl]-phenyl}-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-24-9 (1S,2S,3S,4S)-3,4-Bis-{2-[bis-(4-methoxy-phenyl)-phosphanyl]-phenyl}-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-18-1 (1S,2S,3S,4S)-3,4-Bis-[2-(di-m-tolyl-phosphinoyl)-phenyl]-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-20-5 (1S,2S,3S,4S)-3,4-Bis-[2-(di-p-tolyl-phosphinoyl)-phenyl]-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-15-8 (1S,2S,3S,4S)-3,4-Bis-[2-(diphenyl-phosphinoyl)-phenyl]-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-23-8 (1S,2S,3S,4S)-3,4-Bis-(2-diphenylphosphanyl-phenyl)-cyclobutane-1,2-dicarboxylic acid diethyl ester 
• 835652-32-9 [(1S,2S,3S,4S)-2,3-Bis-(2-diphenylphosphanyl-phenyl)-4-hydroxymethyl-cyclobutyl]-methanol 
• 835652-12-5 (1S,2S,3S,4S)-3,4-Bis-(2-trifluoromethanesulfonyloxy-phenyl)-cyclobutane-1,2-dicarboxylic acid diethyl ester 

Relevant articles and documents

New types of soluble polymer-supported bisphosphine ligands with a cyclobutane backbone for Pd-catalyzed enantioselective allylic substitution reactions

A highly efficient and practical optical resolution of anti head-to-head racemic coumarin dimer 7 has been achieved by molecular complexation with TADDOL, (-)-8, through a hydrogen bonding interaction to afford the corresponding two enantiomers, (-)- and (+)-7, in 70 and 75% yields, respectively, with >99% ee. Starting from enantiopure (-)-7, a new type of C2-symmetric bisphosphine ligand (S,S,S,S)-3 with a cyclobutane backbone has been synthesized in good yield by facile transformations. The asymmetric induction efficiency of these chiral bisphosphine ligands in Pd-catalyzed asymmetric allylic substitution reactions was evaluated. Under the experimental conditions, the allylic substitution products could be obtained in excellent yields (up to 99%) and enantioselectivities (up to 98.9% ee). By taking advantage of the high enantioselectivity of this catalytic reaction and the easily derivable carboxylate groups on the cyclobutane backbone of ligand (S,S,S,S)-3, a new type of analogous ligand (S,S,S,S)-4 as well as the MeO-PEG-supported soluble ligand (S,S,S,S)-5 (PEG = polyethylene glycol) have also been synthesized and utilized in asymmetric allylic substitution reactions. In particular, the MeO-PEG supported (S,S,S,S)-5b had a synergistic effect on the enantioselectivity of the reaction compared with its nonsupported precursor (S,S,S,S)-4c, affording the corresponding allylation products 14a and 14b with excellent enantioselectivities (94.6 and 97.2% ee, respectively). Moreover, the Pd complex of (S,S,S,S)-5b could easily be recovered and recycled several times without significant loss of enantioselectivity and activity in the allylic substitution reactions.