trans-2-(3-pyridyl)cyclopropanemethanol

• 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: trans-2-(3-pyridyl)cyclopropanemethanol
• 英文别名: [(1S,2S)-2-pyridin-3-ylcyclopropyl]methanol
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: QWHJXGUAMZXBPC-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(trans)-ethyl-2-(pyridin-3-yl)cyclopropanecarboxylate	——	C11H13NO2	191.23

反应信息

• 作为反应物：
  描述：

  trans-2-(3-pyridyl)cyclopropanemethanol 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 trans-N,N-dimethyl-[2-(3-pyridyl)cyclopropyl]methylamine
  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：

  2-(3-吡啶基)-1-乙醇 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 xylene 为溶剂， 反应 11.5h， 生成 trans-2-(3-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

文献信息

• Enantioselective Synthesis of cis- and trans-Borocyclopropylmethanol: Simple Building Blocks To Access Heterocycle-Substituted Cyclopropylmethanols
  作者：Saher H. Siddiqui、Chandrasekhar Navuluri、André B. Charette

  DOI：10.1055/s-0037-1611896

  日期：2019.10

  Abstract An enantioselective and non-oxidative methodology was developed to obtain enantioenriched cyclopropyl boronates using a diethanolamine-promoted selective decomplexation of dioxaborolane. The non-oxidative decomplexation of the dioxaborolane ligand from the cyclopropylmethoxide species formed in the dioxaborolane-mediated Simmons–Smith cyclopropanation reaction provided the enantio­enriched

  抽象的 开发了一种对映选择性和非氧化性方法，以利用二乙醇胺促进的二氧杂硼烷的选择性分解来获得对映体富集的环丙基硼酸酯。二氧杂硼烷烷配体从二氧杂硼烷烷介导的Simmons-Smith环丙烷化反应中形成的环丙基甲醇氧化物的非氧化分解，提供了基于对映体富集的CIDA（CIDA = N-环己基次甲基二乙酸）硼环丙烷，产率为92％，产率为95.6：4.4 er。健壮性筛选显示二乙醇胺可与酯，氨基甲酸酯和N-杂环兼容，从而提供了一种工具来获取不仅具有碱敏性而且具有可氧化官能团的对映体富集的环丙烷。发现二乙醇胺与烯丙醇的改进的锌-环丙烷化反应相容，以从相应的顺-N-杂环环丙基甲醇中除去残留的二氧杂硼烷，从而导致产率提高。 开发了一种对映选择性和非氧化性方法，以利用二乙醇胺促进的二氧杂硼烷的选择性分解来获得对映体富集的环丙基硼酸酯。二氧杂硼烷烷配体从二氧杂硼烷烷介导的Simmons-Smith环丙烷化反应
• 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.