2-(hexylamino)-2-phenylethanol | 1032178-53-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(hexylamino)-2-phenylethanol
• CAS: 1032178-53-2
• 化学式: C₁₄H₂₃NO
• 分子量: 221.343
• InChiKey: VIRMEBLCQXPHMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 正己胺 在 iron(III) 1,3,5-benzenetricarboxylate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以49%的产率得到2-(hexylamino)-2-phenylethanol
  参考文献：
  名称：

  金属-有机骨架作为环氧多环选择性开环的高效多相催化剂

  摘要：

  铁基金属有机骨架[Fe（BTC）]（BTC：1,3,5-苯三羧酸酯）是在温和的反应条件下，苯乙烯氧化物与醇和苯胺开环的有效催化剂。在测试的各种用于氧化苯乙烯开环的醇中，就百分比转化率和反应性而言，发现甲醇是最活泼的。环氧乙烷的开环反应速率随醇大小的增加而降低，表明活性位点在微孔中的位置。[Fe（BTC）]是真正的多相催化剂，可以重复使用而不会损失活性。类似化合物[Cu 3（BTC）2尽管活性比[Fe（BTC）]低一些，但]也被认为是有效的。将当前的多相方案与均相催化剂进行比较，以深入了解反应机理。

  DOI：

  10.1002/chem.201000588

文献信息

• Greener aminolysis of epoxides on BiCl3/SiO2
  作者：Farshid Mohsenzadeh、Kioumars Aghapoor、Hossein Reza Darabi、Mohammad Reza Jalali、Mohammad Reza Halvagar

  DOI：10.1016/j.crci.2016.03.011

  日期：2016.8

  Résumé The remarkable catalytic activity of BiCl3/SiO2 for the ring-opening of epoxides with aromatic and aliphatic amines under microwave and thermal heating was observed. This eco-friendly heterogeneous catalyst displayed high to excellent regioselectivity in the synthesis of β-amino alcohols under solvent-free conditions. High turnover frequency (TOF) values under microwave heating and excellent reusability of the catalyst may significantly contribute to applied chemistry.

  摘要 BiCl3/SiO2 在微波和热加热条件下对芳香族和脂肪族胺环氧化物的开环反应具有显著的催化活性。在无溶剂条件下，这种环保型异相催化剂在合成 β-氨基醇时表现出高至优异的区域选择性。该催化剂在微波加热条件下的高翻转频率（TOF）值和优异的可重复使用性可能会极大地促进应用化学的发展。
• Microwave-enhanced bismuth triflate-catalyzed epoxide opening with aliphatic amines
  作者：Thierry Ollevier、Etienne Nadeau

  DOI：10.1016/j.tetlet.2007.12.100

  日期：2008.2

  In the presence of a catalytic amount of Bi(OTf)3·4H2O and under microwave irradiation, neat mixtures of epoxides and amines afforded smoothly the corresponding 2-amino alcohols. A wide variety of aliphatic amines were reacted with cycloalkene oxide, styrene oxide, and stilbene oxide. The reaction proceeded rapidly and afforded the 2-amino alcohols in high up to quantitative yields. All products could

  在催化量的Bi（OTf）3 ·4H 2 O的存在下，在微波辐射下，环氧化物和胺的纯净混合物可平稳地得到相应的2-氨基醇。使多种脂族胺与环氧化烯，氧化苯乙烯和氧化二苯乙烯反应。反应进行得很快，并以高至定量的产率得到了2-氨基醇。通过简单过滤，无需水后处理即可获得所有产品。
• Thiourea catalyzed aminolysis of epoxides under solvent free conditions. Electronic control of regioselective ring opening
  作者：Swapandeep Singh Chimni、Neeraj Bala、Vaibhav A. Dixit、Prasad V. Bharatam

  DOI：10.1016/j.tet.2010.02.053

  日期：2010.4

  A reactant economizing process for the regioselective aminolysis of epoxides using equimolar quantities of reactants catalyzed by the double hydrogen bond donor N,N'-bis[3,5-bis(trifluoromethyl)phenyl]thiourea is reported. Regioselectivity of the reaction is controlled by the electronic nature of the substituent on the styrene oxide, which has been substantiated on the basis of C-13 NMR data and DFT calculations. (C) 2010 Elsevier Ltd. All rights reserved.
• Influence of functionalization of terephthalate linker on the catalytic activity of UiO-66 for epoxide ring opening
  作者：Juan F. Blandez、Andrea Santiago-Portillo、Sergio Navalón、Mónica Giménez-Marqués、Mercedes Álvaro、Patricia Horcajada、Hermenegildo García

  DOI：10.1016/j.molcata.2016.10.022

  日期：2016.12

  A series of five isostructural zirconium terephthalate UiO-66 metal organic frameworks bearing different functional groups on the terephthalate linker (UiO-66-X; X = H, NH2, NO2, Br, CI,) have been successfully prepared and characterized. UiO-66-X materials were evaluated as heterogeneous catalysts for the epoxide ring opening of styrene oxide by methanol, observing an increase in the initial reaction rate from UiO-66-H to UiO-66-Br, over one order of magnitude. The reactivity order, however, does not follow a linear relationship between the Hammett constant value of the substituent and the initial reaction rate. UiO-66-Br exhibits a wide scope, its activity depending on the structure of epoxide and nucleophile. The absence of Zr leaching to the solution together with the preservation of the UiO-66-X crystallinity confirms the stability of the framework under the reaction conditions. Nevertheless, UiO-66 undergoes a progressive deactivation upon reuse that was attributed to a strong adsorption of the reaction product. (C) 2016 Elsevier B.V. All rights reserved.
• Metal-Organic Frameworks as Efficient Heterogeneous Catalysts for the Regioselective Ring Opening of Epoxides
  作者：Amarajothi Dhakshinamoorthy、Mercedes Alvaro、Hermenegildo Garcia

  DOI：10.1002/chem.201000588

  日期：——

  iron‐based metal–organic framework, [Fe(BTC)] (BTC: 1,3,5‐benzenetricarboxylate) is an efficient catalyst in the ring opening of styrene oxide with alcohols and aniline under mild reaction conditions. Out of the various alcohols tested for ring opening of styrene oxide, methanol was found to be the most reactive in terms of percentage conversion and reactivity. The rate of the ring‐opening reaction of

  铁基金属有机骨架[Fe（BTC）]（BTC：1,3,5-苯三羧酸酯）是在温和的反应条件下，苯乙烯氧化物与醇和苯胺开环的有效催化剂。在测试的各种用于氧化苯乙烯开环的醇中，就百分比转化率和反应性而言，发现甲醇是最活泼的。环氧乙烷的开环反应速率随醇大小的增加而降低，表明活性位点在微孔中的位置。[Fe（BTC）]是真正的多相催化剂，可以重复使用而不会损失活性。类似化合物[Cu 3（BTC）2尽管活性比[Fe（BTC）]低一些，但]也被认为是有效的。将当前的多相方案与均相催化剂进行比较，以深入了解反应机理。