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【结 构 式】 
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【分子编号】69183 【品名】Triphenyl phosphine;Triphenyl phosphorous;(triphenylphosphoranylidene)-acetaldehyde 【CA登记号】2136-75-6 |
【 分 子 式 】C18H15PO 【 分 子 量 】278.29 【元素组成】C 77.69% H 5.43% P 11.13% O 5.75% |
合成路线1
该中间体在本合成路线中的序号：(XIX)Intermediates (X) and (XII) are prepared by Wittig olefination of cyclopentylcarboxaldehyde (VII) with (triphenylphosphoranylidene)-acetaldehyde (XIX) in benzene at 80 °C, followed by preparative HPLC separation to yield (E)-3-cyclopentylacrylaldehyde (X), which upon asymmetric aza-Michael reaction with 4-bromopyrazole (XIIIa) by means of a chiral catalyst and p-NBA in THF/H2O gives the Michael adduct (XX). Then, aldehyde (XX) is treated with NH4OH and I2 in 1,4-dioxane/H2O to give nitrile (XXI), which is finally reacted with bis(pinacolato)diboron (XXII) in the presence of Pd(PPh3)4 and KOAc in 1,4-dioxane at 120 °C .
| 【1】 Lin, Q., Meloni, D., Pan, Y. et al. Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-Michael reaction. Org Lett 2009, 11(9): 1999-2002. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIIIa) | 69178 | 4-iodopyrazole;4-Iodo-1H-pyrazole | 3469-69-0 | C3H3IN2 | 详情 | 详情 |
| (B) | 69184 | 2-(bis(3,5-bis(trifluoromethyl)phenyl)((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine | C27H29F12NOSi | 详情 | 详情 | |
| (VII) | 69171 | cyclopentylcarboxaldehyde；Cyclopentanecarbaldehyde;Cyclopentanealdehyde;Cyclopentyl aldehyde;Cyclopentylformaldehyde;Formylcyclopentane | 872-53-7 | C6H10O | 详情 | 详情 |
| (X) | 69176 | (E)-3-cyclopentylacrylaldehyde | C8H12O | 详情 | 详情 | |
| (XII) | 69177 | (S)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile | C17H26BN3O2 | 详情 | 详情 | |
| (XIX) | 69183 | Triphenyl phosphine;Triphenyl phosphorous;(triphenylphosphoranylidene)-acetaldehyde | 2136-75-6 | C18H15PO | 详情 | 详情 |
| (XX) | 69185 | (R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanal | C11H15BrN2O | 详情 | 详情 | |
| (XXI) | 69186 | (R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile | C11H14BrN3 | 详情 | 详情 | |
| (XXII) | 53342 | 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester | 73183-34-3 | C12H24B2O4 | 详情 | 详情 |