4-bromo-piperidine-1,4-dicarboxylic acid monoethyl ester | 1146955-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-bromo-piperidine-1,4-dicarboxylic acid monoethyl ester
• 英文别名: 4-bromo-1-(ethoxycarbonyl)piperidine-4-carboxylic acid；4-bromo-piperidine-1,4-dicarboxylic acid 1-ethyl ester；4-Bromo-1-ethoxycarbonyl-piperidine-4-carboxylic acid；4-bromo-1-ethoxycarbonylpiperidine-4-carboxylic acid
• CAS: 1146955-03-4
• 化学式: C₉H₁₄BrNO₄
• 分子量: 280.118
• InChiKey: LXWSXCVSCNBXDE-UHFFFAOYSA-N

物化性质

• 沸点：
  379.2±42.0 °C(predicted)
• 密度：
  1.585±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三溴甲烷 、 N-乙氧羰基-4-哌啶酮 在 苄基三乙基氯化铵 、 水 、 lithium hydroxide 作用下， 以 叔丁醇 为溶剂， 生成 4-bromo-piperidine-1,4-dicarboxylic acid monoethyl ester
  参考文献：
  名称：

  α，β-不饱和和α-溴代羧酸的改进的合成和体外抗菌活性的研究

  摘要：

  鉴定出一系列α，β-不饱和羧酸和α-溴代羧酸作为有效的抗菌剂。使用肉汤微稀释法评估抗菌活性。所有的酸1-12对9种细菌的实验室控制菌株和2种酵母白色念珠菌都显示出显着的活性。通过在甲醇溶剂中以三乙基苄基氯化铵（TEBA）为催化剂，将酮与溴仿和氢氧化锂水溶液在醇溶剂中进行优化的相转移催化（PTC）反应，可以有效地制备被测酸。

  DOI：

  10.2298/jsc111104016v

文献信息

• One-Step Conversion of Ketones to Conjugated Acids Using Bromoform
  作者：V. D. Vitnik、M. D. Ivanović、Ž. J. Vitnik、J. B. Đorđević、Ž. S. Žižak、Z. D. Juranić、I. O. Juranić

  DOI：10.1080/00397910802531955

  日期：2009.3.25

  Phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent result in the formation of α,β-unsaturated carboxylic acids. The reaction was performed at room temperature for 24 h. The corresponding conjugated acids were obtained from cyclic or aromatic ketones, whereas bromo acids were obtained from 4-oxo-piperidine-1-carboxylic acid ethyl ester (13) and 4-oxo

  摘要 酮与溴仿和氢氧化锂在醇溶剂中的相转移催化 (PTC) 反应导致形成 α,β-不饱和羧酸。反应在室温下进行24小时。相应的共轭酸是从环状或芳香酮中获得的，而溴酸是从 4-氧代-哌啶-1-羧酸乙酯 (13) 和 4-氧代-哌啶-1-羧酸叔丁酯 (14 ）。
• The spectroscopic (FT-IR, FT-Raman, l3C, 1H NMR and UV) and NBO analyses of 4-bromo-1-(ethoxycarbonyl)piperidine-4-carboxylic acid
  作者：Vesna D. Vitnik、Željko J. Vitnik

  DOI：10.1016/j.saa.2014.11.005

  日期：2015.3

  In this work, we will report a combined experimental and theoretical study on molecular and vibrational structure of 4-bromo-1-(ethoxycarbonyl)piperidine-4-carboxylic acid (BEPA). BEPA has been characterized by FT-IR, FT-Raman, H-1 NMR, C-13 NMR and UV spectroscopy. The FT-IR and FT-Raman spectra of BEPA were recorded in the solid phase. The optimized geometry was calculated by B3LYP and M06-2X methods using 6-311G(d,p) basis set. The FT-IR and FT-Raman spectra of BEPA were calculated at the same level and were interpreted in terms of Potential Energy Distribution (PED) analysis. The scaled theoretical wavenumber showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Independent Atomic Orbital (GIAO) method. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using Natural Bond Orbital (NBO) analysis.Density plots over the highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO) energy surface directly identifies the donor and acceptor atoms in the molecule. It also provides information about the charge transfer within the molecule. To obtain chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is plotted over the optimized geometry of the molecule. (C) 2014 Elsevier B.V. All rights reserved.