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- W2914936842 abstract "[1190077-27-0] C16H16N2 (MW 236.32)InChI = InChI=1S/C16H16N2/c1-3-7-13-11(5-1)9-17-15(13)16-14-8-4-2-6-12(14)10-18-16/h1-8,15-18H,9-10H2/t15-,16-/m0/s1InChIKey = LDQOEBZLGBYEEX-HOTGVXAUSA-N(chiral ligand for metal-catalyzed enantioselective reactions)Alternate Name: BIDN (1,1′-biisoindoline).Physical Data: mp 196 °C + 95.0 (c 0.5, CH3OH).Solubility: soluble in THF, DMSO, DMF, and Et2O; modestly soluble in CH2Cl2, CHCl3, MeOH, and CH3CN.From supplied in: clear white powder.Preparative Methods:1 2,2′,3,3′-tetrahydro-1S,1′S-bi-1H-isoindole is prepared through a diaza-cope rearrangement reaction with chiral 1,2-bis(2-hydroxylphenyl)-1,2-diaminoethane, followed by a cyclization process. Condensation of (1R, 2R)-1,2-bis(2-hydroxylphenyl)-1,2-diaminoethane with methyl 2-formylbenzoate via diaza-cope rearrangement at room temperature in EtOH gave the corresponding diimine intermediate 3 in 84% yield. An intramolecular hydrolysis cyclization was initiated with the diimine intermediate in the presence of TFA to afford five-membered lactam 4 in 93% yield. The lactam was protected with (Boc)2O in the presence of DMAP and Et3N in 96% yield, followed by the reduction with BH3·SMe2 in refluxing THF, and the protecting group was removed with TFA to afford the desired diamine in 62% yield (eq 1). (1)Handling, Storage, and Precautions: stable at ambient temperature." @default.
- W2914936842 created "2019-02-21" @default.
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- W2914936842 date "2017-04-11" @default.
- W2914936842 modified "2023-09-24" @default.
- W2914936842 title "2,2′,3,3′-Tetrahydro-1S,1′S-bi-1H-Isoindole" @default.
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- W2914936842 doi "https://doi.org/10.1002/047084289x.rn01999" @default.
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