1-(1,2,3,6-四氢-1-甲基-4-吡啶)-乙酮 | 100752-88-3

• 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: 1-(1,2,3,6-四氢-1-甲基-4-吡啶)-乙酮
• 英文名称: 1-(1,2,3,6-Tetrahydro-1-methyl-4-pyridinyl)-ethanone
• 英文别名: Isoarecolone；1-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)ethanone
• CAS: 100752-88-3
• 化学式: C₈H₁₃NO
• mdl: MFCD00461097
• 分子量: 139.197
• InChiKey: YYJCSIKNHFNEQM-UHFFFAOYSA-N

物化性质

• 沸点：
  225.9±35.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1,2,3,6-四氢-1-甲基-4-吡啶)-乙酮 、 碘甲烷 生成 异槟榔酮甲碘化物
  参考文献：
  名称：

  WATERS, JAMES A.;SPIVAK, CHARLES E.;HERMSMEIER, MARK;YADAV, JANARDAN S.;L+, J. MED. CHEM., 31,(1988) N 3, 545-554

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methyl-4-acetylpyridinium iodide 在 chromium(VI) oxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 1.75h， 生成 1-(1,2,3,6-四氢-1-甲基-4-吡啶)-乙酮
  参考文献：
  名称：

  Synthesis, pharmacology, and molecular modeling studies of semirigid, nicotinic agonists

  摘要：

  Eight nicotinic agonists were synthesized, and their potencies were estimated by contracture of the frog rectus abdominis muscle. The most potent, 1-methyl-4-acetyl-1,2,3,6-tetrahydropyridine methiodide (3b), 50 times as potent as carbamylcholine, served as a template for the rest. Although all of the agonists could easily conform to the putative nicotinic pharmacophore, their potencies spanned a nearly 10,000-fold range. This pharmacophore, therefore, may be necessary but deficient. Computer-assisted molecular modeling studies helped to delineate additional factors that may contribute to potency. The factors are (1) the ground-state conformation, (2) superimposability of the hydrogen bond acceptor and the cationic head onto the template, (3) electrostatic potential at the cationic head and at the hydrogen bond acceptor site, and (4) the presence of a methyl group bonded to the carbon atom that bears the hydrogen bond acceptor. A new program, ARCHEM, was used to calculate and to visualize electrostatic potentials at the van der Waals surfaces of the agonists.

  DOI：

  10.1021/jm00398a010

文献信息

• Nicotinic activity of a series of arecolones and isoarecolones
  申请人：ELI LILLY AND COMPANY

  公开号：EP0537993A1

  公开（公告）日：1993-04-21

  Series of 1,2,5,6-tetrahydro-3-pyridyl ketones and 1,2,3,6-tetrahydro-4-pyridyl ketones and the physiologically acceptable acid addition salts thereof have nicotinic agonist or antagonist activity and are useful in the treatment of Alzheimer's disease, Parkinson's disease and other central nervous system disorders, pain, gastrointestinal disorders, diabetes.

  1,2,5,6-四氢-3-吡啶基酮和1,2,3,6-四氢-4-吡啶基酮及其生理上可接受的酸盐具有烟碱受体激动剂或拮抗剂活性，并可用于治疗阿尔茨海默病、帕金森病和其他中枢神经系统疾病、疼痛、胃肠道疾病、糖尿病。
• The improved convergent syntheses of arecolones and isoarecolone
  作者：John S. Ward、Leander Merritt

  DOI：10.1002/jhet.5570270636

  日期：1990.9

  Good yields of arecolone and isoarecolone were obtained by treating the N,O-dimethylamides of arecaidine and isoarecaidine, respectively, with methylmagnesium chloride. Other substituted arecolones were synthesized by this same strategy.

  通过用甲基氯化镁分别处理槟榔碱和异槟榔碱的N，O-二甲基酰胺，可以得到良好的槟榔酮和异槟榔酮的收率。通过该相同策略合成了其他取代的槟榔酮。
• An improved synthesis of 1-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)ethanone, isoarecolone
  作者：J. Warren Beach

  DOI：10.1002/jhet.5570340637

  日期：1997.11

  A convenient synthesis of 1-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)ethanone, isoarecolone, starting with 4-acetylpyridine is presented. 4-Acetylpyridine was protected as the ketal followed by reaction with iodomethane to give the quaterary salt. The quaterary salt was reduced with sodium borohydride followed by deprotection to give isoarecolone in 80% overall yield.

  提出了一种以4-乙酰基吡啶为起始原料的1-（1,2,3,6-四氢-1-甲基-4-吡啶基）乙酮异戊烯酮的简便合成方法。将4-乙酰基吡啶作为缩酮进行保护，然后与碘甲烷反应，得到季盐。用硼氢化钠还原季盐，然后脱保护得到异丁烯酮，总产率为80％。
• Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance
  申请人：——

  公开号：US20040092508A1

  公开（公告）日：2004-05-13

  This invention relates to use of the combined action of a nicotinic acetylcholine receptor agonist and a monoaminergic substance for the treatment of affective disorders, as well as to pharmaceutical compositions comprising these substances and chemical substances for use according to the invention.

  本发明涉及使用尼古丁型乙酰胆碱受体激动剂和单胺类物质的联合作用治疗情感障碍，以及包含这些物质的制药组合物和用于本发明的化学物质。
• O-substituted tetrahydropyridine oxime cholinergic agents
  申请人：Warner-Lambert Company

  公开号：US04786648A1

  公开（公告）日：1988-11-22

  Certain O-substituted-1,2,5,6-tetrahydro-3- or 1,2,3,6-tetrahydro-4-pyridine oximes are useful as agents for treating pain or for treating the symptoms of senile cognitive decline.

  某些O取代的1,2,5,6-四氢-3-或1,2,3,6-四氢-4-吡啶肟可用作治疗疼痛或治疗老年认知衰退症状的药物。