Synthetic Estrogens. II.¹ Derivatives of 2-Phenylphenanthrene and 1-Ethyl-2-benzylnaphthalene

Metal Free Approach towards the Synthesis of Structurally Diverse 1, 2‐Dihydronaphthalene Scaffolds and Theoretical Investigation

“…It is pertinent to mention that when 1, 2-dihydronaphthalene derivatives like 2 a was treated with a potent dienophile maleic anhydride under refluxing condition in high boiling solvents like dioxane, toluene and DMSO but no trace of Diels-alder adduct was obtained and thus failed to synthesize 2-Phenylphenanthrene derivatives which showed estrogenic activities. [39] Interestingly, the aforementioned procedure was applied for the synthesis of immensely significant [40] conjugated trienes bearing 1,2-dihydronaphthalene (Scheme 2) skeletons (5 a-5 f) through the rearrangement of cyclopropylcarbinol derivatives (4 a-4 f) using TCT-DMF adduct (Table 2). These conjugated trienes are being extensively used as liquid crystals, illuminants, nonlinear optical materials and fluorescent probe for membrane properties.…”

Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori–Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

“…This compound was only partially described; Purified by PTLC ( n -hexane/EtOAc 85:15) as a waxy pale yellow solid (13 mg, 87% yield): [α] D 27 = −11.2 (c = 1, CHCl 3 ); the enantiomeric ratio (94:6 er) was determined by HPLC analysis using a Chiralpack IA column, n -hexane/isopropyl alcohol 90:10, 1 mL/min, 28 °C, t Rmaj = 11.8 min, t Rmin = 13.0 min, 269 nm; 1 H NMR (400 MHz, CDCl 3 ) δ 8.04 (d, J = 8.8 Hz, 1H), 7.14 (d, J = 8.6 Hz, 2H), 6.92–6.78 (m, 3H), 6.66 (d, J = 2.5 Hz, 1H), 3.85 (s, 3H), 3.79 (s, 3H), 3.40 (dd, J = 13.1, 3.3 Hz, 1H), 2.99–2.81 (m, 2H), 2.72–2.55 (m, 2H), 2.08 (dq, J = 13.6, 4.5 Hz, 1H), 1.83–1.70 (m, 1H); 13 C­{ 1 H} NMR (101 MHz, CDCl 3 ) δ 198.5, 163.6, 158.1, 146.7, 132.3, 130.4, 130.2, 126.3, 113.9, 113.2, 112.6, 55.5, 55.3, 49.4, 35.0, 29.1, 27.7; HRMS (ESI) m / z [M + H] + calcd for C 19 H 21 O 3 + 297.1485, found 297.1486.…”