(+/-)-ethyl 3-piperidinobutanoate | 42980-68-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-ethyl 3-piperidinobutanoate
• 英文别名: 3-piperidino-butyric acid ethyl ester；3-Piperidino-buttersaeure-aethylester；Ethyl 3-(1-piperidyl)butanoate；ethyl 3-piperidin-1-ylbutanoate
• CAS: 42980-68-7
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: MXBAHQQGCQCOQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  125 °C(Press: 13 Torr)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-ethyl 3-piperidinobutanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 3-N-Piperidinobutanol
  参考文献：
  名称：

  Carbamoylcholine homologs: synthesis and pharmacology at nicotinic acetylcholine receptors

  摘要：

  In a recent study, racemic 3-(N,N-dimethylamino)butyl-N,N-dimethylcarbamate (1) was shown to be a potent agonist at neuronal nicotinic acetylcholine receptors with a high selectivity for nicotinic over muscarinic acetylcholine receptors [Mol. Pharmacol. 64 (2003) 865-875]. Here we present the synthesis and pharmacological characterization of a series of analogs of 1, where the methyl group at C-3 has been replaced by different alkyl substituents. Ring systems have been incorporated into the carbon backbone of some of the molecules, or the amino group has been build into ring systems. Furthermore, the (+)- and (-)-enantiomers of I have been separated, and X-ray crystallography has revealed that (-)-1 possesses (S)-configuration. The compounds have been characterized pharmacologically at recombinant nicotinic receptor subtypes. The structure-activity relationship study has provided valuable insight into the mode of interactions of I and its analogs with neuronal nicotinic acetylcholine receptors. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2004.06.038
• 作为产物：
  描述：

  2-methyl-2-piperidino-1-ethoxycarbonylethene 在 乙醇 、 铂 作用下， 生成 (+/-)-ethyl 3-piperidinobutanoate
  参考文献：
  名称：

  Takagi et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 1592

  摘要：

  DOI：

文献信息

• Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds
  申请人：Yale University

  公开号：US06384282B2

  公开（公告）日：2002-05-07

  The present invention is directed to a process for addition of amines to carbon-carbon double bonds in a substrate, comprising: reacting an amine with a compound containing at least one carbon-carbon double bond in the presence a transition metal catalyst under reaction conditions effective to form a product having a covalent bond between the amine and a carbon atom of the former carbon-carbon double bond. The transition metal catalyst comprises a Group 8 metal and a ligand containing one or more 2-electron donor atoms. The present invention is also directed to enantioselective reactions of amine compounds with compounds containing carbon-carbon double bonds, and a calorimetric assay to evaluate potential catalysts in these reactions.

  本发明涉及一种将胺添加到底物中的碳-碳双键的过程，包括：在存在过渡金属催化剂的条件下，将胺与至少含有一个碳-碳双键的化合物反应，以形成产物，其中胺与前述碳-碳双键的碳原子之间形成共价键。过渡金属催化剂包括第8族金属和含有一个或多个2电子给体原子的配体。本发明还涉及胺化合物与含有碳-碳双键的化合物的对映选择性反应，以及用于评估这些反应中潜在催化剂的热量测定分析。
• Efficient Copper-Catalyzed Chemo Selective Conjugate Addition of Aliphatic Amines to α,β-Unsaturated Compounds in Water
  作者：Chun-Gu Xia、Li-Wen Xu、Jing-Wei Li、Shao-Lin Zhou、Xiao-Xue Hu

  DOI：10.1055/s-2003-42125

  日期：——

  The first environmentally benign, highly efficient, conjugate addition of aliphatic amines to α,β-unsaturated compounds catalyzed by simple copper salts in the green solvent, water is described.

  描述了在绿色溶剂中，通过简单的铜盐催化，脂肪胺与 α,β-不饱和化合物的第一个环境友好、高效、共轭加成。
• ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions
  作者：Mohammed M. Hashemi、Bagher Eftekhari-Sis、Amir Abdollahifar、Behzad Khalili

  DOI：10.1016/j.tet.2005.10.006

  日期：2006.1

  At room temperature, ZrOCl2·8H2O on montmorillonite K10 efficiently catalyzes conjugate addition of amines to a variety of conjugated alkenes such as α,β-unsaturated carbonyl compounds, carboxylic esters, nitriles and amides under solvent-free conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.

  在室温下，在无溶剂条件下，蒙脱石K10上的ZrOCl 2 ·8H 2 O有效地催化了胺与各种共轭烯烃（如α，β-不饱和羰基化合物，羧酸酯，腈和酰胺）的共轭加成反应。催化剂可以再循环用于随后的反应，而没有任何明显的效率损失。
• Drake; McElvain, Journal of the American Chemical Society, 1934, vol. 56, p. 698
  作者：Drake、McElvain

  DOI：——

  日期：——
• Kjaer; Petersen, Acta Chemica Scandinavica (1947), 1951, vol. 5, p. 1145,1148
  作者：Kjaer、Petersen

  DOI：——

  日期：——