658699-37-7

Basic information

• Product Name: Ketone, 5-hydroxy-4-indanyl methyl (5CI)
• Synonyms: Ketone, 5-hydroxy-4-indanyl methyl (5CI)
• CAS NO: 658699-37-7
• Molecular Formula: C11H12O2
• Molecular Weight: 176.21178
• Product Categories: CYCLOHEXANE
• Mol File: 658699-37-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 123.8-125.3 °C
• Boiling Point: 327.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.186±0.06 g/cm3(Predicted)
• PKA: 10.58±0.20(Predicted)
• CAS DataBase Reference: Ketone, 5-hydroxy-4-indanyl methyl (5CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ketone, 5-hydroxy-4-indanyl methyl (5CI)(658699-37-7)
• EPA Substance Registry System: Ketone, 5-hydroxy-4-indanyl methyl (5CI)(658699-37-7)

Safety Data

• Hazardous Substances Data: 658699-37-7(Hazardous Substances Data)

Relevant articles and documents

Chasing Polycyclic Natural Products: 5/6/5- or 5/6/6-Carbotricyclic Scaffold Construction via Stereodivergent Diels-Alder Reaction of Chiral Hydrindanes and Their Boron Complexes

Chiral trans-hydrindanes (bicyclo[4.3.0]nonanes) are important building blocks of polycyclic natural products. In order to access 5/6/5- and 5/6/6-carbotricyclic scaffolds scope and limitation of [4+2] cycloadditions of tetrahydroindanones with various dienes were studied. Cyclopentadiene gave a tetracylic endo-(R,R)-diastereomer under acid-catalysis, whereas thermal conditions provided the endo-(S,S)-diastereomer with the opposite diastereofacial selectivity. The stereodivergent outcome was rationalized by high-level quantum-chemical computations which revealed the acid-catalysis to be a kinetically controlled reaction and the thermal cycloaddition to be under thermodynamic control. Stereochemical assignment of the cycloadducts was facilitated by conversion of the 1,3-dicarbonyls with BF3 ? OEt2 into BF2-chelate complexes. Subsequent thermal Diels-Alder reaction of BF2- or BBN-chelates (from 9-BBN-OTf) gave endo/exo-mixtures of the (R,R)- and (S,S)-diastereomers, while more elevated temperatures yielded primarily the endo/exo-(S,S)-diastereomers. Thermal [4+2] cycloadditions with 2,3-dimethylbutadiene proceeded with lower diastereoselectivity as the reaction was kinetically controlled according to calculations. Attempted Diels-Alder-reactions with furan gave furyl-substituted indanones rather than cycloadducts.