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(S,S)-[447440-43-9] C13H18ClNOSi (MW 267.83) InChI = 1S/C13H18ClNOSi/c1-4-10-17(14)15(3)11(2)13(16-17)12-8-6-5-7-9-12/h4-9,11,13H,1,10H2,2-3H3/t11-,13+,17?/m0/s1 InChIKey = XHCRAANIMMYPDV-APBZJUGRSA-N (R,R)-[596851-24-0] InChI = 1S/C13H18ClNOSi/c1-4-10-17(14)15(3)11(2)13(16-17)12-8-6-5-7-9-12/h4-9,11,13H,1,10H2,2-3H3/t11-,13+,17?/m1/s1 InChIKey = XHCRAANIMMYPDV-HWURVSIFSA-N (chiral allylsilane reagent used for the asymmetric allylation of aldehyde- and ketone-derived N-acylhydrazones, as well as allylation and cinnamylation of N-2-hydroxyphenyl in addition to N-2-hydroxybenzyl aldimines) Physical Data: bp ∼120 °C at ∼5mmHg; d 1.085 g cm−3. Solubility: sol CH2Cl2, CHCl3, ClCH2CH2Cl, benzene, toluene, trifluorotoluene, ether, and most other organic solvents; not compatible with protic solvents (e.g., H2O, MeOH), and Lewis basic solvents (e.g., acetone, DMSO) may negatively impact performance. Form Supplied in: colorless/light yellow liquid; reagent and its enantiomer are commercially available. Preparation and Purification: both enantiomers of the allylsilane reagent are readily prepared from commercially available allyltrichlorosilane, (S,S)- or (R,R)-pseudoephedrine, and Et3N in CH2Cl2 at 0 °C for 12 h. Following filtration of the triethylamine salts, distillation under reduced pressure provides the pure reagent in ∼80% yield as a 2:1 mixture of diastere-omers (unassigned).1 Handling, Storage, and Precautions: moisture sensitive, reacts with water and protic solvents possibly resulting in HCl vapor generation. Storage in a Schlenk flask under N2 or Ar in a freezer is recommended. If reagent performance degrades due to exposure to moisture or due to very long storage time, it may simply be redistilled under reduced pressure. |
