词条 | N-Methylconiine |
释义 |
| Watchedfields = changed | verifiedrevid = 425008398 | Name = N-Methylconiine | ImageFile = nme-coniine.svg | ImageSize = 240px | ImageName = N-Methylconiine | IUPACName = 1-Methyl-2-propylpiperidine |Section1 = {{Chembox Identifiers |Section2 = {{Chembox Properties |C=9|H=19|N=1 |BoilingPtC = 173 to 174 |Density = (D) 0.8318 g cm−3 at 24.3 °C (L) 0.8349 g cm−3 at 20 °C }} N-Methylconiine is a poisonous alkaloid found in poison hemlock in small quantities. Isolation and propertiesThe D-(+)-stereoisomer of N-methylconiine is reported to occur in hemlock in small quantities,[1] and methods for its isolation are described by Wolffenstein[2] and by von Braun.[3] It is a colourless, oily, coniine-like liquid, specific rotation [α]D +81.33° at 24.3 °C. The salts are crystalline ("B" marks one molecule of the base): the hydrochloride, B•HCl, forms masses of needles, mp. 188 °C; the platinichloride, B2•H2PtCl6, has mp. 158 °C. The L-(−)-stereoisomer was obtained by Ahrens[4] from residues left in the isolation of coniine as hydrobromide or by removing coniine as the nitroso-compound. It is a colourless, coniine-like liquid, bp. 175.6 °C/767 mmHg, specific rotation [α]D −81.92° at 20 °C. The monohydrochloride crystallises in leaflets, mp. 191–192 °C; the monohydrobromide in leaflets, mp. 189–190 °C; the platinichloride in orange crystals, mp. 153–154 °C; the aurichloride in leaflets, mp. 77–78 °C; and the picrate in long needles, mp. 121–122 °C. SynthesisN-Methyl-D-coniine was prepared by the action of potassium methyl sulfate on coniine by Passon.[5] Hess and Eichel[6] have shown that D-coniine with formaldehyde and formic acid yields an active N-methyl-D-coniine, and that methyl-isopelletierine hydrazone yields N-methyl-DL-coniine when heated with sodium ethoxide at 150–170 °C. References1. ^Planta and Kekulé, Annalen, 1854, 89, 150. {{DEFAULTSORT:Methylconiine, N-}}2. ^Ber., 1894, 27, 2615; 1895, 28, 302 3. ^Ber., 1905, 38, 3108; 1917, 50, 1477. 4. ^Ber., 1902, 35, 1330; cf. Löffler and Friedrich, ibid., 1909, 42, 107. 5. ^Ber., 1891, 24, 1678. 6. ^Ber., 1917, 50, 1386; 1919, 52, 1622; 1920, 53, 129. 2 : Piperidine alkaloids|Neurotoxins |
随便看 |
|
开放百科全书收录14589846条英语、德语、日语等多语种百科知识,基本涵盖了大多数领域的百科知识,是一部内容自由、开放的电子版国际百科全书。