Methyl 3-pyridin-3-ylpyrrolidine-1-carboxylate | 178483-10-8

• 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: Methyl 3-pyridin-3-ylpyrrolidine-1-carboxylate
• CAS: 178483-10-8
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: OLAWNLNKGFISBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 3-pyridin-3-ylpyrrolidine-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 異菸鹼
  参考文献：
  名称：

  Regioselective synthesis of 3-aryl substituted pyrrolidines via palladium catalyzed arylation: pharmacological evaluation for central dopaminergic and serotonergic activity.

  摘要：

  A series of 3-arylpyrrolidines has been synthesised via palladium catalyzed arylation and evaluated for dopaminergic and serotonergic activity in vitro and in vivo. Compounds substituted by electron withdrawing groups on the meta position of the aromatic ring, were found to be preferential dopamine autoreceptor antagonists. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00618-x
• 作为产物：
  描述：

  3-吡啶基三氟甲磺酸酯 在 palladium diacetate 、 palladium on activated charcoal 三(2-呋喃基)膦 、 甲酸铵 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Methyl 3-pyridin-3-ylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Regioselective synthesis of 3-aryl substituted pyrrolidines via palladium catalyzed arylation: pharmacological evaluation for central dopaminergic and serotonergic activity.

  摘要：

  A series of 3-arylpyrrolidines has been synthesised via palladium catalyzed arylation and evaluated for dopaminergic and serotonergic activity in vitro and in vivo. Compounds substituted by electron withdrawing groups on the meta position of the aromatic ring, were found to be preferential dopamine autoreceptor antagonists. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00618-x

文献信息

• Regiochemical Control and Suppression of Double Bond Isomerization in the Heck Arylation of 1-(Methoxycarbonyl)-2,5-dihydropyrrole
  作者：Clas Sonesson、Mats Larhed、Camilla Nyqvist、Anders Hallberg

  DOI：10.1021/jo952112s

  日期：1996.1.1

  additive excluded the use of silver and thallium salts, but high regioselectivity and good yields could be obtained by employing tri-2-furylphosphine as ligand. Arylation was rendered both regioselective and enantioselective (58% ee) with 1-naphthyl triflate as substrate utilizing a (R)-BINAP/thallium acetate combination. The C-3 arylated enamides were converted further into the corresponding 3-arylpyrrolidines

  在标准的Heck反应条件下1-（甲氧基羰基）-2，5-二氢吡咯的丙烯酸化产生化合物的混合物。烯烃经历两种类型的钯催化反应：（a）芳基化以提供C-3芳基化衍生物和（b）竞争性双键异构化。碳酸银和乙酸th的加入完全抑制了异构化，并且在用芳基卤化物芳基化之后获得了C-3取代的化合物的良好产率。关于芳基三氟甲磺酸酯作为芳基化剂，必须添加氯化锂以促进Heck反应。该添加剂不使用银盐和th盐，但是通过使用三-2-呋喃基膦作为配体可以获得较高的区域选择性和良好的产率。利用（R）-BINAP /乙酸al的组合，以三氟甲磺酸1-萘酯为底物使区域选择性和对映选择性（58％ee）都呈丙烯酸化。将C-3芳基化的酰胺进一步转化为相应的3-芳基吡咯烷。
• Regioselective synthesis of 3-aryl substituted pyrrolidines via palladium catalyzed arylation: pharmacological evaluation for central dopaminergic and serotonergic activity.
  作者：Clas Sonesson、Håkan Wikström、Martin W Smith、Kjell Svensson、Arvid Carlsson、Nicholas Waters

  DOI：10.1016/s0960-894x(96)00618-x

  日期：1997.2

  A series of 3-arylpyrrolidines has been synthesised via palladium catalyzed arylation and evaluated for dopaminergic and serotonergic activity in vitro and in vivo. Compounds substituted by electron withdrawing groups on the meta position of the aromatic ring, were found to be preferential dopamine autoreceptor antagonists. (C) 1997, Elsevier Science Ltd.