(S)-2-(ethylamino)-1-phenylethanol | 1312607-88-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(ethylamino)-1-phenylethanol
• 英文别名: (1S)-2-(ethylamino)-1-phenylethanol
• CAS: 1312607-88-7
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: XAFJIMVZKZUFPE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (S)-2-(ethylamino)-1-phenylethanol 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙基苯 、 甲苯 为溶剂， 反应 6.0h， 生成 methyl 2-((6S)-4-ethyl-2-oxo-6-phenylmorpholin-3-yl)acetate
  参考文献：
  名称：

  ANTIFUNGAL COMPOUNDS

  摘要：

  本发明涉及一系列已被证明具有抗真菌活性的新化合物。因此，该发明涉及新化合物、其制备方法、包含它们的药物组合物以及用作药物，尤其是抗真菌药物的化合物。

  公开号：

  US20120252801A1
• 作为产物：
  描述：

  (S)-2-氨基-1-苯乙醇 、 乙醛 在 sodium tetrahydroborate 、 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以86%的产率得到(S)-2-(ethylamino)-1-phenylethanol
  参考文献：
  名称：

  [EN] ANTIFUNGAL COMPOUNDS
  [FR] COMPOSÉS ANTIFONGIQUES

  摘要：

  本发明涉及一系列已被证明具有抗真菌活性的新化合物。因此，该发明涉及新化合物、其制备方法、包含它们的药物组合物以及用作药物，尤其是抗真菌药物的化合物。

  公开号：

  WO2011072345A1

文献信息

• Efficient Routes to a Diverse Array of Amino Alcohol-Derived Chiral Fragments
  作者：Sina Haftchenary、Shawn D. Nelson、Laura Furst、Sivaraman Dandapani、Steven J. Ferrara、Žarko V. Bošković、Samuel Figueroa Lazú、Adrian M. Guerrero、Juan C. Serrano、DeMarcus K. Crews、Cristina Brackeen、Jeffrey Mowat、Thomas Brumby、Marcus Bauser、Stuart L. Schreiber、Andrew J. Phillips

  DOI：10.1021/acscombsci.6b00050

  日期：2016.9.12

  Efficient syntheses of chiral fragments derived from chiral amino alcohols are described. Several unique scaffolds were readily accessed in 1–5 synthetic steps leading to 45 chiral fragments, including oxazolidinones, morpholinones, lactams, and sultams. These fragments have molecular weights ranging from 100 to 255 Da and are soluble in water (0.085 to >15 mM).

  描述了衍生自手性氨基醇的手性片段的有效合成。在1-5个合成步骤中，很容易获得几个独特的支架，这些支架导致45个手性片段，包括恶唑烷酮，吗啉酮，内酰胺和sultams。这些片段的分子量为100至255 Da，可溶于水（0.085至> 15 mM）。
• 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-
• 2-(2-Oxo-morpholin-3-yl)-acetamide Derivatives as Broad-Spectrum Antifungal Agents
  作者：Dorothée Bardiot、Karin Thevissen、Katrijn De Brucker、Annelies Peeters、Paul Cos、Carlos P. Taborda、Michael McNaughton、Louis Maes、Patrick Chaltin、Bruno P. A. Cammue、Arnaud Marchand

  DOI：10.1021/jm501814x

  日期：2015.2.12

  From a fungicidal screen, we identified 2-(2-oxo-morpholin-3-yl)-acetamide derivatives as fungicidal agents against Candida species, additionally characterized by antifungal activity against Aspergillus species. However, development of this series was hampered by low plasmatic stability. Introduction of a gem-dimethyl on the 6-position of the morpholin-2-one core led to considerable improvement in plasmatic stability while maintaining in vitro antifungal activity. Further optimization of the series resulted in the discovery of N-(biphenyl-3-ylmethyl)-2-(4-ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)acetamide (87), which, in addition to fungicidal activity against Candida species, shows promising and broad antifungal in vitro activity against various fungi species, such as molds and dermatophytes. In vivo efficacy was also demonstrated in a murine model of systemic Candida albicans infection with a significant fungal load reduction in kidneys.
• 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.
• [EN] ANTIFUNGAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIFONGIQUES
  申请人：UNIV LEUVEN KATH

  公开号：WO2011072345A1

  公开（公告）日：2011-06-23

  The present invention relates to a series of novel compounds which have been shown to possess antifungal activity. The invention therefore relates to the new compounds, methods for their preparation, pharmaceutical compositions comprising them and to the compounds for use as a medicament, more in particular antifungal medicament.

  本发明涉及一系列已被证明具有抗真菌活性的新化合物。因此，该发明涉及新化合物、其制备方法、包含它们的药物组合物以及用作药物，尤其是抗真菌药物的化合物。