135513-03-0

Basic information

• Product Name: (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal
• Synonyms: (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal
• CAS NO: 135513-03-0
• Molecular Weight: 434.578
• Mol File: 135513-03-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal(135513-03-0)
• EPA Substance Registry System: (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal(135513-03-0)

Safety Data

• Hazardous Substances Data: 135513-03-0(Hazardous Substances Data)

Upstream product

• 52340-78-0 (R,R)-hydroxybenzoin 
• 135513-01-8 1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde 
• 101271-57-2 1,1a,2,3,4,4a,5,5a,6,7,8,8a,9,10-tetradecahydro-1:4,5:8-dimethanoanthracene-9,10-diol 
• 135513-02-9 1,4:5,8-dimethano-1,2,3,4,5,6,7,8-octahydro-9,10-dimethoxyanthracene 
• 2065-48-7 endo-cis-anti-cis-endo-1,2,3,4,4a,5,6,7,8,8a,9a,10a-Dodecahydro-1,4:5,8-dimethanoanthracene-9,10-dione 
• 78548-82-0 1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 

Relevant articles and documents

Electronically tuned chiral ruthenium porphyrins: Extremely stable and selective catalysts for asymmetric epoxidation and cyclopropanation

We report the use of three enantiomerically pure and electronically tuned ruthenium carbonyl porphyrin catalysts for the asymmetric cyclopropanation and epoxidation of a variety of olefinic substrates. The D4-symmetric ligands carry a methoxy, a methyl or a trifluoromethyl group at the 10-position of each of the 9-[anti-(1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene)]-substituents at the meso-positions of the porphyrin. Introduction of a CF 3-substituent in this remote position resulted in greatly improved catalyst stability, and turnover numbers of up to 7500 were achieved for cyclopropanation, and up to 14200 for epoxidation, with ee values typically >90% and ≈80%, respectively. In one example, the axial CO ligand at the ruthenium was exchanged for PF3, resulting in the first chiral ruthenium porphyrin with a PF3 ligand reported to date. In cyclopropanations with ethyl diazoacetate, the latter catalyst performed exceedingly well, and gave a 95% ee in the case of 1,1-diphenylethylene as substrate.

Catalytic Asymmetric Epoxidation of Unfunctionalized Alkenes Using the First D4-Symmetric Metallotetraphenylporphyrin

The condensation of the resolved C2-symmetric benzaldehyde, 1,2,3,4,5,6,7,8-octahydro-1:4,5:8-dimethanoanthracene-9-carboxaldehyde, with pyrrole produced a new chiral tetraphenylporphyrin exhibiting D4 symmetry.A manganese chloride complex of this porphyrin was used as a catalyst (0.5 mol percent) for the asymmetric epoxidation of aromatic-substituted alkenes in the presence of excess sodium hypochlorite, providing for terminal or Z alkene yields above 90 percent and enantioselectivities ranging from 41 to 76 percent ee.