1-(2-nitro-1-phenyl-ethyl)-piperidine | 138783-48-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-nitro-1-phenyl-ethyl)-piperidine
• 英文别名: 1-(2-Nitro-1-phenyl-aethyl)-piperidin；1-(2-nitro-1-phenylethyl)piperidine
• CAS: 138783-48-9
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: WYDWOPOSKUSBGA-UHFFFAOYSA-N

物化性质

• 沸点：
  350.1±35.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  哌啶 、 β-硝基苯乙烯 在 magnesia 作用下， 反应 0.05h， 以84%的产率得到1-(2-nitro-1-phenyl-ethyl)-piperidine
  参考文献：
  名称：

  MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction

  摘要：

  通过改进的溶胶-凝胶技术制备的MgO纳米颗粒具有较窄的粒径分布。合成的氧化镁纳米颗粒在无溶剂条件下于室温下作为高效催化剂，用于一系列α,β-不饱和羰基化合物和硝基烯烃的氮迈克尔加成反应中，以及胺的加成反应，从而获得高产率的β-氨基羰基和β-硝基胺。该催化剂可回收并在至少五次连续运行中重复使用而不会损失活性。

  DOI：

  10.1007/s13738-013-0338-x

文献信息

• Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions
  作者：Fatemeh Tamaddon、Mohammad Tayefi、Elaheh Hosseini、Elham Zare

  DOI：10.1016/j.molcata.2012.08.027

  日期：2013.1

  Iranian dolomite (CaMg(CO3)(2)) which consists of double-layered carbonates with Ca2+ and Mg2+ ions was utilized as a heterogeneous base catalyst in the C-C, C-N, and C-S bond forming reactions via the Henry, Knoevenagel, aza-Michael, and thia-Michael transformations under mild conditions in water. Iranian dolomite has been characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer Emmett Teller (BET) and XRF chemical analysis, while its basic strength was evaluated by following the Hammett indicators procedure. This water-insoluble natural catalyst demonstrated high activity and was reusable. (c) 2012 Elsevier B.V. All rights reserved.
• Nucleophilic addition to olefins. 16. Unusual substituent effects in the reaction of amines with .beta.-nitrostyrenes. Solvent effect on intrinsic rate constants
  作者：Claude F. Bernasconi、Richard A. Renfrow、Paul R. Tia

  DOI：10.1021/ja00275a047

  日期：1986.7
• Worrall, Journal of the American Chemical Society, 1927, vol. 49, p. 1604
  作者：Worrall

  DOI：——

  日期：——
• Kinetic Study on Michael-Type Reactions of β-Nitrostyrenes with Cyclic Secondary Amines in Acetonitrile: Transition-State Structures and Reaction Mechanism Deduced from Negative Enthalpy of Activation and Analyses of LFERs
  作者：Ik-Hwan Um、Ji-Sun Kang、Jong-Yoon Park

  DOI：10.1021/jo4007442

  日期：2013.6.7

  A kinetic study is reported for the Michael-type reactions of X-substituted beta-nitrostyrenes (1a-j) with a series of cyclic secondary amines in MeCN. The plots of pseudo-first-order rate constant k(obsd) vs [amine] curve upward, indicating that the reactions proceed through catalyzed and uncatalyzed routes. The dissection of k(obsd) into Kk(2) and Kk(3) (i.e., the rate constants for the uncatalyzed and catalyzed routes, respectively) revealed that Kk(3) is much larger than Kk(2), implying that the reactions proceed mainly through the catalyzed route when [amine] > 0.01 M. Strikingly, the reactivity of beta-nitrostyrene (1g) toward piperidine decreases as the reaction temperature increases. Consequently, a negative enthalpy of activation is obtained, indicating that the reaction proceeds through a relatively stable intermediate. The Bronsted-type plots for the reactions of 1g are linear with beta(nuc) = 0.51 and 0.61, and the Hammett plots for the reactions of 1a-j are also linear with pX = 0.84 and 2.10 for the uncatalyzed and catalyzed routes, respectively. The reactions are concluded to proceed through six-membered cyclic transition states for both the catalyzed and uncatalyzed routes. The effects of the substituent X on reactivity and factors influencing beta(nuc) and pX obtained in this study are discussed.