137365-09-4

Basic information

• Product Name: (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL
• Synonyms: (R,R)-(-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL;(-)-DINOL;(4R-TRANS)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRA(2-NAPHTHYL)-1,3-DIOXOLANE-4,5-DIMETHANOL;(4R,5R)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRA(2-NAPHTHYL)DIOXOLANE-4,5-DIMETHANOL;(-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL;(4R-trans)-2,2-di-me-A,A,A,A-tetra-2-nap -dioxo;(4R,5R)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetra(2-naphthyl)dioxolane-4,5-di;(4R-TRANS)-2 2-DI-ME-A A A' A'-TETRA-2-&
• CAS NO: 137365-09-4
• Molecular Formula: C₄₇H₃₈O₄
• Molecular Weight: 666.8
• Mol File: 137365-09-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 213-216 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.269g/cm³
• Refractive Index: 1.718
• Storage Temp.: 2-8°C
• BRN: 6168481
• CAS DataBase Reference: (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL(137365-09-4)
• EPA Substance Registry System: (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL(137365-09-4)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 137365-09-4(Hazardous Substances Data)

Usage

Uses

(4R,5R)-2,2-Dimethyl-α,α,α'',α''-tetra-2-naphthalenyl-1,3-dioxolane-4,5-dimethanol, is a privileged ligand analogue of TADDOLs. It can be broadly used in asymmetric synthesis. It is also shown that the titanium TADDOLate catalysts have broad application towards carbonyl addition and cycloaddition.

InChI:InChI=1/C47H38O4/c1-45(2)50-43(46(48,39-23-19-31-11-3-7-15-35(31)27-39)40-24-20-32-12-4-8-16-36(32)28-40)44(51-45)47(49,41-25-21-33-13-5-9-17-37(33)29-41)42-26-22-34-14-6-10-18-38(34)30-42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m1/s1

Upstream product

• 580-13-2 2-bromonaphthalene 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 1236286-39-7 C₁₄H₁₆N₂*C₄₇H₃₈O₄ 

Downstream Products

• 1236286-39-7 C₁₄H₁₆N₂*C₄₇H₃₈O₄ 
• 1158430-51-3 6-(3-diphenylphosphanylbiphenyl-2-yloxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 
• 1158430-58-0 6-(2,4-di-tert-butyl-6-diphenylphosphanylphenoxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 
• 1158430-56-8 6-(2-tert-butyl-6-diphenylphosphanylphenoxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 
• 1158430-53-5 6-(2-diphenylphosphanyl-6-isopropylphenoxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 

Relevant articles and documents

Optical monitoring of gases with cholesteric liquid crystals

A new approach to optical monitors for gases is introduced using cholesteric liquid crystals doped with reactive chiral compounds. The approach is based on cholesteric pitch length changes caused by a change in helical twisting power (HTP) of the chiral dopants upon reaction with the analyte. The concept is demonstrated for monitoring carbon dioxide via reversible carbamate formation and for oxygen using the irreversible oxidation of a chiral dithiol to a disulfide. Monitoring of CO2 was achieved by doping a commercial cholesteric liquid crystalline mixture (E7) with 1.6% mol of the 1:1 complex of an optically pure diamine with a TADDOL derivative. Upon exposure to carbon dioxide, the reflection band of a thin film of the mixture shifted from 637 to 495 nm as a consequence of dissociation of the complex after carbamate formation of the diamine. An O2 monitor was obtained by doping E7 with a chiral binaphthyl dithiol derivative and a nonresponsive codopant. The reflection band of the oxygen monitor film changed from 542 to 600 nm, due to the conformational change accompanying oxidation of the dithiol to disulfide. These monitoring mechanisms hold promise for application In smart packaging, where carbon dioxide and oxygen are of special interest because of their roles in food preservation.

Phosphite-Catalyzed C?H Allylation of Azaarenes via an Enantioselective [2,3]-Aza-Wittig Rearrangement

A phosphite-mediated [2,3]-aza-Wittig rearrangement has been developed for the regio- and enantioselective allylic alkylation of six-membered heteroaromatic compounds (azaarenes). The nucleophilic phosphite adducts of N-allyl salts undergo a stereoselective base-mediated aza-Wittig rearrangement and dissociation of the chiral phosphite for overall C?H functionalization of azaarenes. This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both the allyl part and azaarenes. Catalysis with chiral phosphites is also demonstrated with synthetically useful yields and enantioselectivities.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.