1-(2,2-diethoxyethyl)-4-phenyl-1,2,5,6-tetrahydropyridine | 143017-49-6

• 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
• 英文名称: 1-(2,2-diethoxyethyl)-4-phenyl-1,2,5,6-tetrahydropyridine
• 英文别名: 1-(2,2-diethoxyethyl)-4-phenyl-3,6-dihydro-2H-pyridine
• CAS: 143017-49-6
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: LCEJMYCCGNAEDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,2-diethoxyethyl)-4-phenyl-1,2,5,6-tetrahydropyridine 在 盐酸 作用下， 反应 4.0h， 生成 (+/-)-endo-6-hydroxy-4-phenyl-1-azabicyclo<3.2.1>oct-3-ene hydrochloride
  参考文献：
  名称：

  Intramolecular Cyclization with Oxocarbenium Ion. Synthesis of 1-Azabicyclo[3.3.1]nonene and [3.2.1]octene Derivatives

  摘要：

  Hydroxy- and aryl-substituted 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives have been synthesized by the intramolecular cationic cyclization of 4-aryl-1,2,5,6-tetrahydropyridines bearing an acetal moiety in the nitrogen substituent. Factors governing the stereoselectivity of the ring closure step have been disclosed. Two compounds were resolved into the enantiomers and the absolute configuration of one of them was deduced from CD investigations. Among the new compounds substances with valuable antiamnesic effect have been found.

  DOI：

  10.3987/com-94-6975
• 作为产物：
  描述：

  1,2,3,6-四氢-4-苯基吡啶盐酸盐 、 2-溴-1,1-二乙氧基乙烷 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1-(2,2-diethoxyethyl)-4-phenyl-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Intramolecular Cyclization with Oxocarbenium Ion. Synthesis of 1-Azabicyclo[3.3.1]nonene and [3.2.1]octene Derivatives

  摘要：

  Hydroxy- and aryl-substituted 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives have been synthesized by the intramolecular cationic cyclization of 4-aryl-1,2,5,6-tetrahydropyridines bearing an acetal moiety in the nitrogen substituent. Factors governing the stereoselectivity of the ring closure step have been disclosed. Two compounds were resolved into the enantiomers and the absolute configuration of one of them was deduced from CD investigations. Among the new compounds substances with valuable antiamnesic effect have been found.

  DOI：

  10.3987/com-94-6975

文献信息

• [EN] NEW 1-AZABICYCLOALKANE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESS FOR PREPARING SAME
  申请人：GYÓGYSZERKUTATÓ INTÉZET KV.

  公开号：WO1992007854A1

  公开（公告）日：1992-05-14

  (EN) The invention relates to new 1-azabicycloalkane derivatives and their stereoisomers of general formula (I), wherein R1 représents a phenyl, substituted phenyl, naphthyl or thienyl group, wherein the phenyl group can be substituted by one or several halogen atom(s), methyl, methoxy, methylthio or trifluoromethyl group(s), R2 represents a hydrogen atom or a C2-5 aliphatic acyl group, R3 represents a hydrogen atom or a methyl group, n can be zero or one, the dotted line can optionally represent a further C-C bond and the wavy line means that the respective substituent can be bound to the carbon atom in either of the two steric positions, furthermore their pharmaceutically acceptable acid addition salts. Furthermore, the invention relates to a process for preparing the above compounds and pharmaceutical compositions containing the same. The compounds of general formula (I) have valuable therapeutic, mainly antiamnesic, activity.(FR) Nouveaux dérivés d'azabicycloalcane-1 et leurs stéréoisomères répondant à la formule générale (I), dans laquelle R1 représente un groupe phényle, phényle substitué, naphtyle ou thiényle, où le groupe phényle peut être substitué par un ou plusieurs atomes d'halogène ou groupes méthyle, méthoxy, méthylthio ou trifluorométhyle; R2 représente un atome d'hydrogène ou un groupe acyle aliphatique C2-5; R3 représente un atome d'hydrogène ou un groupe méthyle; n peut être 0 ou 1; la ligne pointillée peut éventuellement représenter une liaison C-C supplémentaire et la ligne ondulée signifie que le substituant respectif peut être lié à l'atome de carbon au niveau de l'une ou l'autre des deux positions stériques; ainsi que leurs sels d'addition acide pharmaceutiquement acceptables. On a également prévu un procédé de préparation des composés précités et des compositions pharmaceutiques les contenant. Les composés répondant à la formule générale (I) présentent une précieuse activité thérapeutique, principalement anti-amnésique.

  该发明涉及新的1-氮杂双环烷衍生物及其立体异构体，其通式为（I），其中R1代表苯基，取代苯基，萘基或噻吩基，其中苯基可以被一个或多个卤素原子，甲基，甲氧基，甲硫基或三氟甲基基团取代，R2代表氢原子或C2-5脂肪酰基团，R3代表氢原子或甲基，n可以为零或一，虚线可以选择性地表示进一步的C-C键，而波浪线表示相应的取代基可以与碳原子中的任一二立体位置结合，此外还包括其药学上可接受的酸加成盐。此外，该发明还涉及制备上述化合物和含有它们的药物组合物的方法。通式（I）的化合物具有有价值的治疗作用，主要是抗遗忘症作用。
• NEW 1-AZABICYCLOALKANE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESS FOR PREPARING SAME
  申请人：GYOGYSZERKUTATO INTEZET K.V.

  公开号：EP0556342A1

  公开（公告）日：1993-08-25
• Intramolecular Cyclization with Oxocarbenium Ion. Synthesis of 1-Azabicyclo[3.3.1]nonene and [3.2.1]octene Derivatives
  作者：Sándor Sólyom、Gizella Ábrahám、Márta Szöllõsy、István Pallagi、Emese Csuzdi、István Ling、Beáta Vitális、Katalin Horváth、Edit J. Horváth、László G. Hársing Jr.、Judit Kajtár

  DOI：10.3987/com-94-6975

  日期：——

  Hydroxy- and aryl-substituted 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives have been synthesized by the intramolecular cationic cyclization of 4-aryl-1,2,5,6-tetrahydropyridines bearing an acetal moiety in the nitrogen substituent. Factors governing the stereoselectivity of the ring closure step have been disclosed. Two compounds were resolved into the enantiomers and the absolute configuration of one of them was deduced from CD investigations. Among the new compounds substances with valuable antiamnesic effect have been found.