(R/S)-2-(hexylamino)-1-phenylethanol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R/S)-2-(hexylamino)-1-phenylethanol
• 英文别名: 2-(hexylamino)-1-phenylethanol
• 化学式: C₁₄H₂₃NO
• mdl: MFCD12177789
• 分子量: 221.343
• InChiKey: JLSYXSVZYCGXKG-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：
  0.571
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R/S)-2-(hexylamino)-1-phenylethanol 在 溴 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 1-hexyl-2-phenylaziridine
  参考文献：
  名称：

  Ga 催化温度依赖性恶唑烷酮/哌嗪的合成，涉及发散配体辅助机制的苯基氮丙啶

  摘要：

  介绍了二元Ga基催化剂体系在CO 2和氮丙啶偶联形成恶唑烷酮中的应用。已经可以优化催化剂体系，以在相对温和的反应条件下以优异的收率选择性地形成单一区域异构体。优化的催化剂体系已成功应用于一系列由氧化苯乙烯衍生的取代氮丙啶。已经观察到带有两个芳族取代基的氮丙啶通过意想不到的二聚反应导致哌嗪形成。这些哌嗪产物可以在没有CO 2的情况下选择性地形成或在较低的反应温度下有利。对两种产物形成的反应机理进行了详细的 DFT 研究，并确定了恶唑烷酮合成中不寻常的配体辅助作用。更具体地说，这种配体相互作用促进了氮丙啶的初始开环，这项工作提出了第一个完全阐明的涉及该中间体的机制。

  DOI：

  10.1002/adsc.202300537
• 作为产物：
  描述：

  3-hexyl-5-phenyloxazolidin-2-one 在 sodium hydroxide 作用下， 以 二乙二醇 为溶剂， 以83%的产率得到(R/S)-2-(hexylamino)-1-phenylethanol
  参考文献：
  名称：

  Wrobel; Bobin; Karczewski, Polish Journal of Chemistry, 2006, vol. 80, # 6, p. 907 - 912

  摘要：

  DOI：

文献信息

• Immobilized Pseudomonas sp. lipase: A powerful biocatalyst for asymmetric acylation of (±)-2-amino-1-phenylethanols with vinyl acetate
  作者：Deniz Yildirim、S. Seyhan Tükel

  DOI：10.1016/j.procbio.2013.04.019

  日期：2013.5

  gram of support (%) and recovered activity (%). A 4-factor and 3-level Box–Behnken design was applied for the acylation of (±)-2-(propylamino)-1-phenylethanol, a model substrate, with vinyl acetate and the asymmetric acylations of other (±)-2-amino-1-phenylethanols with different alkyl substituents onto nitrogen atom such as (±)-2-(methylamino)-1-phenylethanol, (±)-2-(ethylamino)-1-phenylethanol,

  摘要假单胞菌属。脂肪酶通过席夫碱的形成固定在戊二醛活化的 Florisil® 载体上，并通过用氰基硼氢化钠还原席夫碱来稳定。根据每克载体的结合蛋白 (%) 和恢复活性 (%) 评估固定性能。将 4 因子和 3 级 Box-Behnken 设计应用于 (±)-2-(丙基氨基)-1-苯基乙醇（模型底物）与乙酸乙烯酯的酰化以及其他 (±)-2 的不对称酰化-氨基-1-苯基乙醇在氮原子上具有不同的烷基取代基，例如 (±)-2-(甲氨基)-1-苯基乙醇、(±)-2-(乙氨基)-1-苯基乙醇、(±)-2-(丁氨基)-1-苯基乙醇和(±)-2-(己基氨基)-1-苯基乙醇在优化条件下进行。最佳条件为体积含水量为 1.8%，反应温度为 51.5 °C，乙酸乙烯酯与氨基醇的初始摩尔比为 1.92，固定化脂肪酶负载量为 47 mg mL-1。被测氨基醇的 (R)-对映异构体优先被酰化，反应完全发生在 2-氨基-
• 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.
• Optimization of immobilization conditions of Mucor miehei lipase onto Florisil via polysuccinimide spacer arm using response surface methodology and application of immobilized lipase in asymmetric acylation of 2-amino-1-phenylethanols
  作者：Deniz Yildirim、S. Seyhan Tükel、Özlem Alptekin、Dilek Alagöz

  DOI：10.1016/j.molcatb.2013.12.003

  日期：2014.2

  In this study, the immobilization of Mucor miehei lipase onto Florisil((R)) support via polysuccinimide spacer arm was scrutinized by using a 3-factor and 3-level Box-Behnken design. The independent parameters were immobilization pH, immobilization time and initial lipase concentration and the response was the specific activity of immobilized lipase. A quadratic equation was used to explain the relationship between the response and independent parameters. After analysis of variance test, coefficient of determination and adjusted coefficient of determination values were estimated as 0.98 and 0.94, respectively. The optimal immobilization pH, immobilization time and initial lipase concentration were determined as 6.0, 7h and 1.1 mg mL(-1), respectively, after desirability analysis. The specific activity values for three individual experiments were observed as 25.88 +/- 0.73, 26.06 +/- 0.47 and 25.96 +/- 0.52 U mg protein(-1) under the optimized conditions. The hydrolytic activities of free and immobilized lipase preparations were characterized using p-nitrophenyl palmitate as substrate. The esterification activity of immobilized lipase preparation was evaluated by asymmetric acylation of 2-(methylamino)-1-phenylethanol, 2-(ethylamino)-1-phenylethanol, 2-(butylamino)-1-phenylethanol, and 2-(hexylamino)-1-phenylethanol with vinyl acetate. The acylation protocol was optimized in terms of the effects of initial water amount, reaction temperature, molar ratio of amino alcohol to vinyl acetate, biocatalyst loading, organic medium and kind of lipases used. The developed protocol provided a facile methodology for the preparation of enantiopure 2-amino-1-phenylethanols which may be used as potential new beta-adrenergic receptor antagonists. (C) 2013 Elsevier B.V. All rights reserved.