3-氰基-1-甲基-1,2,5,6-四氢吡啶 | 5657-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-氰基-1-甲基-1,2,5,6-四氢吡啶
• 英文名称: 3-cyano-1-methyl-1,2,5,6-tetrahydropyridine
• 英文别名: 3-cyano-1,2,5,6-tetrahydro-1-methylpyridine；5-cyano-1-methyl-1,2,3,6-tetrahydropyridine；1-methyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile；1-Methyl-1,2,5,6-tetrahydro-pyridin-3-carbonitril；1-methyl-3-cyano-1,2,5,6-tetrahydropyridine；1-methyl-5-cyano-1,2,3,6-tetrahydropyridine；1-methyl-3,6-dihydro-2H-pyridine-5-carbonitrile
• CAS: 5657-66-9
• 化学式: C₇H₁₀N₂
• mdl: MFCD18445925
• 分子量: 122.17
• InChiKey: VVYCNKGYADUXMA-UHFFFAOYSA-N

物化性质

• 沸点：
  92-93 °C(Press: 11 Torr)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氰基-1-甲基-1,2,5,6-四氢吡啶 在 盐酸 作用下， 生成 1,2,5,6-四氫-1-甲菸鹼酸
  参考文献：
  名称：

  Wohl; Johnson, Chemische Berichte, 1907, vol. 40, p. 4714

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 作用下， 生成 3-氰基-1-甲基-1,2,5,6-四氢吡啶
  参考文献：
  名称：

  Wohl; Johnson, Chemische Berichte, 1907, vol. 40, p. 4714

  摘要：

  DOI：

文献信息

• Lipophillically-substituted piperidine oxadiazolyl compounds and their
  申请人：A/S Ferrosan

  公开号：US04837241A1

  公开（公告）日：1989-06-06

  New piperidine compounds having the formula ##STR1## wherein at least one of R.sup.3, R.sup.4, and R.sup.5 are ##STR2## and the other independently are H, C.sub.1-6 -alkyl, wherein R' is H, C.sub.1-8 -alkyl, phenyl, thienyl, cyclopropyl, or C.sub.1-3 -alkoxymethyl; and R.sup.1 and R.sup.6 independently are H or C.sub.1-6 -alkyl, and wherein ##STR3## and salts thereof with pharmaceutically-acceptable acids. The new compounds are useful in improving the cognitive functions of the forebrain and hippocampus of mammals, and are therefore useful in the treatment of Alzheimer's disease.

  新的哌啶化合物具有以下结构式：其中R.sup.3、R.sup.4和R.sup.5中至少有一个是##STR2##，另外的独立地是H、C.sub.1-6-烷基，其中R'是H、C.sub.1-8-烷基、苯基、噻吩基、环丙基或C.sub.1-3-烷氧甲基；R.sup.1和R.sup.6独立地是H或C.sub.1-6-烷基，其中##STR3##及其与药用可接受酸的盐。这些新化合物对改善哺乳动物前脑和海马的认知功能有用，因此对治疗阿尔茨海默病有用。
• FUSED HETEROCYCLIC COMPOUND AND MEDICINAL USE THEREOF
  申请人：Mitsubishi Pharma Corporation

  公开号：EP1396488A1

  公开（公告）日：2004-03-10

  The fused heterocyclic compound of the present invention, which is represented by the formula (I): wherein each symbol is as defined in the specification, an optically active form thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a water adduct thereof show poly(ADP-ribose) synthase inhibitory action and are useful as therapeutic drugs for cerebral infarction.

  本发明的融合杂环化合物，其化学式表示为（I）：其中每个符号如规范中定义，其光学活性形式，其药学上可接受的盐，其水合物和水加合物显示聚(ADP-核糖)合酶抑制作用，并可用作治疗脑梗死的药物。
• 1,2,3-Triazole and tetrazole substituted piperidine or
  申请人：H. Lundbeck A/S

  公开号：US04866077A1

  公开（公告）日：1989-09-12

  The present invention relates to novel compounds of the following formula, where the dotted line designates an optional bond: ##STR1## wherein "het" designates a five membered heterocyclic ring which may include 1 or 2 double bonds and 1-4 heteroatoms selected from nitrogen, oxygen or sulphur, provided that "het" may not designate a 1,2,4- or 1,3,4-oxadiazole; R.sup.1 is selected from hydrogen, lower alkyl, optionally substituted with phenyl which may be substituted with halogen, lower alkyl, or lower alkoxy, or a group R.sup.6 --CO--NH--CH.sub.2 -- or R.sup.6 --O--CO--, wherein R.sup.6 is lower alkyl, branched or unbranched, or phenyl optionally substituted with halogen, trifluoromethyl, lower alkyl, hydroxy, lower alkoxy, or lower acyloxy; R.sup.2 and R.sup.3 are the same or different, each representing hydrogen, lower alkyl, cycloalkyl (3-6 C-atoms), lower alkenyl, lower alkadienyl, lower alkynyl, optionally substituted with hydroxy, halogen or phenyl, in which the phenyl group may be substituted with halogen, trifluoromethyl, lower alkyl, hydroxy or lower alkoxy; R.sup.2 and R.sup.3 may further, respectively, be selected from trifluoromethyl or phenyl optionally substituted with halogen, trifluoromethyl, lower alkyl, hydroxy, lower alkoxy or lower acyloxy, or R.sup.2 and R.sup.3 may, respectively, be a group OR.sup.7 or SR.sup.7 wherein R.sup.7 is defined as R.sup.2 or R.sup.3, and if "het" includes 2 or more carbon atoms, R.sup.4 and R.sup.5 are the same or different, and each is defined as R.sup.2 or R.sup.3, and if "het" includes only one carbon atom, there is only one substituent, R.sup.4, on the heterocyclic ring, and R.sup.4 is defined as R.sup.2 or R.sup.3, as well as individual stereo isomers and pharmaceutically acceptable acid addition salts thereof. The invention moreover relates to methods for the preparation of the compounds of formula I, to novel intermediates, to pharmaceutical compositions containing same and to methods for the treatment of disorders, caused by malfunction of the acetylcholine (AcCh) or muscarinic system, by administering a non-toxic effective amount of a compound of formula I.

  本发明涉及以下式的新化合物，其中虚线表示可选键：##STR1##其中“het”表示一个五元杂环，可能包括1或2个双键和1-4个从氮、氧或硫中选择的杂原子，但“het”不能表示1,2,4-或1,3,4-噁二唑；R.sup.1选择自氢、较低的烷基，可选地取代为苯基，苯基可能被卤素、较低的烷基或较低的烷氧基取代，或者是一个基团R.sup.6--CO--NH--CH.sub.2--或R.sup.6--O--CO--，其中R.sup.6是较低的烷基、支链或直链，或者是可选地取代为卤素、三氟甲基、较低的烷基、羟基、较低的烷氧基或较低的酰氧基的苯基；R.sup.2和R.sup.3相同或不同，各自代表氢、较低的烷基、环烷基（3-6个碳原子）、较低的烯基、较低的烷二烯基、较低的炔基，可选地取代为羟基、卤素或苯基，其中苯基可能被卤素、三氟甲基、较低的烷基、羟基或较低的烷氧基取代；R.sup.2和R.sup.3还可以分别选择三氟甲基或可选地取代为卤素、三氟甲基、较低的烷基、羟基、较低的烷氧基或较低的酰氧基的苯基，或者R.sup.2和R.sup.3可以分别是一个基团OR.sup.7或SR.sup.7，其中R.sup.7定义为R.sup.2或R.sup.3，如果“het”包括2个或更多个碳原子，则R.sup.4和R.sup.5相同或不同，各自定义为R.sup.2或R.sup.3，如果“het”只包括一个碳原子，则在杂环上只有一个取代基R.sup.4，R.sup.4定义为R.sup.2或R.sup.3，以及其单独的立体异构体和药学上可接受的酸盐。此外，本发明还涉及制备式I化合物的方法，新的中间体，含有相同化合物的药物组合物，以及通过给予式I化合物的非毒性有效量来治疗由乙酰胆碱（AcCh）或肌碱系统功能障碍引起的疾病的方法。
• Heilmittelchemische Studien in der heterocyclischen Reihe. 27. Mitteilung Hydropyridine I Die Reduktion von 1-Methyl-3-cyan-pyridiniumjodid mit Natriumborhydrid
  作者：K. Schenker、J. Druey

  DOI：10.1002/hlca.19590420626

  日期：——

  Reduction of 1-methyl-3-cyano-pyridinium iodide with excess sodium borohydride has been found to give l-methyl-3-cyano-l,2,5,6-tetrahydro-pyridine (I) and l-methyl-3-cyano-l,6-dihydro-pyridine (II a) in approximately equal yields.The constitution of IIa was deduced by comparison with l-methyl-3-cyano-1,4-dihydro-pyridine (II b), obtained exclusively on treatment of 1-methyl-3-cyano-pyridinium iodide

  已经发现用过量的硼氢化钠还原1-甲基-3-氰基-吡啶鎓碘化物可得到1-甲基-3-氰基-1、2,5,6-四氢吡啶（I）和1-甲基-3-甲基。氰基-1-，6-二氢吡啶（IIa）的收率大致相等。通过与仅在上位获得的1-甲基-3-氰基-1,4-二氢吡啶（IIb）的比较推论得出IIa的结构用连二亚硫酸钠处理1-甲基-3-氰基吡啶鎓碘化物，并通过催化加氢生成1-甲基-3-氰基-1,4,5,6-四氢吡啶（III）。
• Heilmittelchemische Studien in der heterocyclischen Reihe. 29. Mitteilung. Hydropyridine III. Die Anlagerung von Phenylacetonitril an 1-Methyl-3-cyan-1,6-dihydro-pyridin
  作者：K. Schenker、J. Druey

  DOI：10.1002/hlca.19590420728

  日期：——

  Base-catalysed addition of phenylacetonitrile to 1-methyl-3-cyano-1, 6-dihydropyridine (II) is shown to give α-[1-methyl-3-cyano-1.4.5.6-tetrahydro-pyridyl-(4)]-phenylacetonitrile (VI). The structure of VI has been proved by its reduction to the saturated dicyano compound VIII, which has also been synthesized by the MICHAEL- type addition of phenylacetonitrile to 1-methyl-3-cyano-l.2.5.6-tetrahydro-pyridine

  已显示碱催化将苯乙腈加至1-甲基-3-氰基-1，6-二氢吡啶（II）中，得到α-[1-甲基-3-氰基-1.4.5.6-四氢吡啶基-（4）]-苯基乙腈（VI）。通过将VI还原成饱和的二氰基化合物VIII来证明VI的结构，该化合物也通过将苯乙腈向1-甲基-3-氰基-1.2.5.6-四氢吡啶（IX）进行MICHAEL型加成而合成。