ethyl trans-2-(4-pyridyl)cyclopropanecarboxylate

• 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: ethyl trans-2-(4-pyridyl)cyclopropanecarboxylate
• 英文别名: trans-ethyl 2-(pyridin-4-yl)cyclopropanecarboxylate；ethyl (1S,2S)-2-pyridin-4-ylcyclopropane-1-carboxylate
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: UGYNFXSWOUTZCL-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl trans-2-(4-pyridyl)cyclopropanecarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以98%的产率得到trans-2-(4-pyridyl)cyclopropanemethanol
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of some (pyridyl)cyclopropylmethyl amines and their methiodides as nicotinic receptor ligands

  摘要：

  A series of 3- and (4-pyridyl)cyclopropyimethyl amines and their quaternary ammonium derivatives have been synthesized; they can be considered as rigid analogues of nicotine. The compounds have been tested on rat cerebral cortex to measure the affinity for the central nicotinic receptor. Only the methiodides show affinity in the micromolar range. The results obtained can provide useful information on the topography of the nicotinic receptor-binding site. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01234-x
• 作为产物：
  描述：

  4-溴吡啶 、 potassium (trans-2-(ethoxycarbonyl)cyclopropyl)trifluoroborate 在 palladium diacetate 、 caesium carbonate 、 正丁基二(1-金刚烷基)膦 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 以85%的产率得到ethyl trans-2-(4-pyridyl)cyclopropanecarboxylate
  参考文献：
  名称：

  功能化的1,2-二取代环丙基三氟硼酸酯的多谱图合成和C-C / C-N偶联

  摘要：

  基于Pd（II）或Cu（I）催化的三氟硼酸乙烯基酯与重氮化合物的反应，开发了一种方便的方法，用于功能化的1,2-二取代的环丙基三氟硼酸酯的多谱合成。优化的方案允许将目标产物制备为数克级的纯非对映异构体。结果表明，标题化合物是Suzuki-Miyaura和Chan-Lam反应的良好偶联伙伴，可提供与医学相关的（杂）芳基环丙烷，具有高非对映选择性。

  DOI：

  10.1002/adsc.201900879

文献信息

• Multigram Synthesis and C−C/C−N Couplings of Functionalized 1,2‐Disubstituted Cyclopropyltrifluoroborates
  作者：Oleksandr V. Hryschuk、Yevhen Yurov、Andriy V. Tymtsunik、Volodymyr O. Kovtunenko、Igor V. Komarov、Oleksandr O. Grygorenko

  DOI：10.1002/adsc.201900879

  日期：2019.12.3

  A convenient approach to the multigram synthesis of functionalized 1,2‐disubstituted cyclopropyltrifluoroborates was developed, based on Pd(II)‐ or Cu(I)‐catalyzed reaction of vinyltrifluoroborate and diazo compounds. Optimized protocols allowed for the preparation of the target products as pure diastereomers on multigram scale. It was shown that the title compounds were good coupling partners for

  基于Pd（II）或Cu（I）催化的三氟硼酸乙烯基酯与重氮化合物的反应，开发了一种方便的方法，用于功能化的1,2-二取代的环丙基三氟硼酸酯的多谱合成。优化的方案允许将目标产物制备为数克级的纯非对映异构体。结果表明，标题化合物是Suzuki-Miyaura和Chan-Lam反应的良好偶联伙伴，可提供与医学相关的（杂）芳基环丙烷，具有高非对映选择性。
• Synthesis and pharmacological evaluation of some (pyridyl)cyclopropylmethyl amines and their methiodides as nicotinic receptor ligands
  作者：Luca Guandalini、Silvia Dei、Dina Manetti、Maria Novella Romanelli、Serena Scapecchi、Elisabetta Teodori、Katia Varani

  DOI：10.1016/s0014-827x(02)01234-x

  日期：2002.5

  A series of 3- and (4-pyridyl)cyclopropyimethyl amines and their quaternary ammonium derivatives have been synthesized; they can be considered as rigid analogues of nicotine. The compounds have been tested on rat cerebral cortex to measure the affinity for the central nicotinic receptor. Only the methiodides show affinity in the micromolar range. The results obtained can provide useful information on the topography of the nicotinic receptor-binding site. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.