Indane, 1-phenyl

Ninhydrin liefert in saurem Milieu liber das l,3-Dihydroxy-2-oxo-indan 1,2,3-Trihy-droxy-indan. In alkalischem Milieu wird der Fiinfring reduktiv aufgespalten, und man erhalt u. a. (2-Formyl-phenyl)-glykolsaure12. 

It is noteworthy that the value of this substrate is smaller by one order compared to non-cyclic compounds. According to the discussions proposed above, this is considered to be due to its conformation already being fixed to the one that fits to the binding site of the enzyme. This estimation was demonstrated to be true by the examination of the effect of temperature on the kinetic parameters. Arrhenius plots of the rate constants of indane dicarboxylic acid and phenyl-malonic acid showed that the activation entropies of these substrates are —27.6 and —38.5 calmol K , respectively. The smaller activation entropy for the cyclic compound demonstrates that the 5yn-periplanar conformation of the substrate resembles the one of the transition state. 

Hydrosilylation of o-allylstyrene (82) with trichlorosilane in the presence of 0.3mol% of a palladium catalyst bearing triphenylphosphine has been found to produce a mixture of indane (83) and the open-chain products (84) and (85) (Scheme 11). The reaction of styrene with trichlorosilane gave a quantitative yield of 1-phenyl-l-(trichlorosilyl)ethane whereas allylbenzene did not give silylation products under the same reaction conditions. These results show that the hydropalladation process is operative in the hydrosilylation of styrene derivatives with trichlorosilane catalysed by palladium-phosphine complexes." ... 

The proposed mechanism of the indan-forming reaction was supported by an experiment in which 3-methyl-3-phenyl-l-chlorobutane was treated with potassium in cyclohexane at 80 , as reported by Pines and Schaap (4 ). 1,1-Dimethylindan was produced under these conditions of low temperature and pressure, however, side reactions produced some tert-pen-tylbenzene and 3-methyl-3-phenyl-l-butene. The major products, however, were 2,5-dimethyl-2,5-diphenylhexane and ethylene. [See Reactions (18-20).] The formation of 2,5-dimethyl-2,5-diphenylhexane results from... 

Watanabe N, Ikeno A, Minato H, et al. Discovery and preclinical characterisation of (-l-)-3-[4-(l-piperidinoethoxy)phenyl]spiro[indene-l,l -indane]-5,5 -diol hydrochloride a promising nonsteroidal estrogen receptor agonist for hot flush. / Med Chem 2003 46 3961-4. 

Anisindione Anisindione, 3-(/7-methoxyphenyl)indan-l,3-dion (24.2.11), differs from phenidione only in the presence of a p-methoxy group in the phenyl ring, and it is synthesized in the same manner as phenindione, but by using p-methoxybenzaldehyde or p-methoxyphenylacetic acid [30-32]. 

The syntheses of benzosilacyclopentenes have been tabulated (b-82MH2000). The pyrolysis of phenyl-substituted tris(trimethylsilyl)methylsilanes affords a novel route to 1,3-disilain-danes. The fluoride (101) decomposes with loss of trimethylfluorosilane, probably via a series of interconverting silaalkene intermediates, to give the three indanes (102)-(104)... 

Dimethylaminoethyl)-indan-l-one Phenyl lithium Maleic acid... 

The use of co-(2-bromophenyl)alkyl-2-oxazolines (13) in base-promoted ring-closure reactions provides a good access to 1-phenyl-indane and 1-phenyl-tetralin derivatives (14) that contain easily manipulated oxazoline moieties. Satisfactory isolated yields of cyclized products 14 are obtained with lithium diisopropylamide (LDA) in THF at room temperature under irradiation with UV light, even when quaternary centers are formed (Scheme 10.39) [55]. The yield of 14 (n= 1, R= Ph) increases to 75% when the reaction proceeds under laboratory light for 48 h at room temperature. 

Process chemists studied an approach to 8 using the readily available indan-1-one-3-carboxylic acid 20 prepared from phenyl succinic anhydride via Friedel-Crafts closure (Scheme 6). After esterification (yielding 21), homologation of the carbonyl via aminomethylation proceeded in high efficiency to give 25. In the presence of... 

Activated ketones, for example isatin136 or acenaphthenequinone,137 have been similarly condensed with 92 at ca. 150° for several hours with acetic acid and sodium acetate forming, for example, 94, 3, or 42. Fusing 87 (R = Ph) with excess phthalic anhydride in the presence of an alkaline catalyst gives (84%) spiro[2-oxo-3-phenyl-4-thioxo-l,3-thiazolidine-5,2 -indane-1, 3 -dione] (95).117... 

Cross-linking reactions require an intermolecular Friedel-Crafts reaction between tertiary cations and positions of the phenyl group made less reactive by the presence of bulky groups on the indane structure. Electrophilic attack of benzylic cation 29 (Fig. 5) upon unsubstituted positions of the phenyl group of 15 is sterically inhibited. 

Figure 5 Electrophilic attack of benzylic carbenium ion upon monomer or unsubstituted positions of the phenyl group of the indane polymer unit.

Borsenberger et al. (1995a) measured electron mobilities of PS doped with a series of acceptor molecules 2-r-butyl-9,10-N,N -dicyanoanthraquinone-diimine (DCAQ), 2-methy 1-2-pentyl-1,3-bis(dicyanomethylene)indane (DCMI), 3,5-dimethyl-3, 5 -diisopropyl-4,4,-diphenoquinone (DPQ-A), N,N -bis(l, 2-di-methylpropyl)-l,4,5,8-naphthalenetetracarboxylic diimide (NTDI), and 1,1-dioxo-2-(4-methylphenyl)-6-phenyl-4-(dicyanomethylidene)thiopyran (PTS). The reduction potentials are -0.22, -0.34, -0.45, -0.56, and -0.15 V, respectively. The dipole moments are between 0.30 and 4.0 Debye. In all materials, the field and temperature dependencies were described as logu oc pE1/2 and -(T0/rP)2. Figure 33 shows the results for 40% NTDI doped PS. The results... 

Shu-Jiang and co-workers [76] have developed a green approach for the synthesis of biologically important indeno[2,l-c]pyrazolo[5,4-/7]pyridines 36 via a MCR of a suitable aldehyde, 3-methyl-l-phenyl-l//-pyrazol-5-amine and 1,3-indane-dione in water under microwave irradiation without the aid of any catalyst. This protocol has the prominent advantages of being environmentally benign and having... 

Glykolsaure (3,4-Methylendioxy-phenyl)- -nitril Vl/ld, 426f. Indan 2-Nitro-l-oxo- Vl/ld, 13 Indol... 

Glykoisaure 3-(bzw.4)-Methyl-phenyl- -nitril Vl/ld, 426 f. Indan 2-Amino-l-oxo- (Hydrochlo-rid) XI/l, 904 lH-Indol... 

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