2-(4'-fluorophenyl)-2-(phenylamino)ethanol | 1178128-22-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4'-fluorophenyl)-2-(phenylamino)ethanol
• 英文别名: 2-(4-Fluorophenyl)-2-(phenylamino)ethanol；2-anilino-2-(4-fluorophenyl)ethanol
• CAS: 1178128-22-7
• 化学式: C₁₄H₁₄FNO
• 分子量: 231.27
• InChiKey: DKOVQIINSOTVLC-UHFFFAOYSA-N

物化性质

• 沸点：
  377.4±27.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-fluorophenyl)-N-methyl-N-(methylsulfonyl)-2-(phenylamino)acetamide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 0.33h， 生成 2-(4'-fluorophenyl)-2-(phenylamino)ethanol
  参考文献：
  名称：

  Gold-Catalyzed 1,2-Difunctionalizations of Aminoalkynes Using Only N- and O-Containing Oxidants

  摘要：

  We report two viable routes for the 1,2difunctionalization of aminoalkynes using only oxidants. In the presence of a gold catalyst, nitrones enable the oxoamination of aminoalkynes 1 to form 2-aminoamides 2. With a suitable gold catalyst, nitrosobenzenes implement an alkyne/nitroso metathesis of the same substrates to give 2-oxoiminylamides 3. These two novel oxidations also provide 1,2-aminoalcohols with opposite regioselectivity via NaBH4 reduction in situ.

  DOI：

  10.1021/ja208150d

文献信息

• Brønsted Acid‐Catalysed Epoxide Ring‐Opening Using Amine Nucleophiles: A Facile Access to <i>β</i> ‐Amino Alcohols
  作者：Aparna Tyagi、Naveen Yadav、Jabir Khan、Sankalan Mondal、Chinmoy Kumar Hazra

  DOI：10.1002/asia.202200379

  日期：2022.7.15

  A transition metal-free facile access to β-amino alcohols via epoxide ring-opening with amine nucleophiles. The process is carried out at room temperature with only 0.5 mol % catalyst loading. A wide spectrum of styrene oxide and aniline derivatives are readily tolerated by this procedure. A highly effective gram-scale synthesis with a high TON=842 is also reported.

  通过与胺亲核试剂的环氧化物开环，一种不含过渡金属的容易获得β-氨基醇的方法。该方法在室温下进行，催化剂负载量仅为 0.5 mol%。该程序很容易耐受广谱的氧化苯乙烯和苯胺衍生物。还报道了具有高 TON=842 的高效克级合成。
• Biocatalytic aminohydroxylation of styrenes for efficient synthesis of enantiopure β-amino alcohols
  作者：Ruiwen Hu、Anjie Gong、Langxing Liao、Yan-Xin Zheng、Xin Liu、Peng Wu、Fushuai Li、Huili Yu、Jing Zhao、Long-Wu Ye、Binju Wang、Aitao Li

  DOI：10.1016/s1872-2067(22)64174-3

  日期：2023.1

  A general biocatalytic process of intermolecular aminohydroxylation of styrenes with aniline has been achieved for efficient one-pot preparation of enantiopure β-amino alcohols. The reaction involves first asymmetric epoxidation of alkene substrates by a heme-dependent monooxygenase (P450) or the FAD-dependent styrene monooxygenase, followed by the aminolysis of nascent epoxide intermediates with aniline

  已经实现了苯乙烯与苯胺分子间氨基羟基化的通用生物催化过程，用于高效一锅法制备对映体纯β- 氨基醇。该反应涉及首先通过血红素依赖性单加氧酶 (P450) 或 FAD 依赖性苯乙烯单加氧酶对烯烃底物进行不对称环氧化，然后在水溶液中用苯胺氨解新生环氧化物中间体。混合簇连续体 (HCC) 模型计算揭示了环氧化物与苯胺的氨解机理以及水在调节此类反应中的关键作用。此外，结合实验和模拟表明，氨基醇的手性由酶促反应中形成的环氧化物的绝对构型决定。总之，所开发的生物催化工艺为生产高附加值对映体纯β提供了一种高效、环保的方法-氨基醇，从廉价且容易获得的烯烃开始。
• 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.
• Gold-Catalyzed 1,2-Difunctionalizations of Aminoalkynes Using Only N- and O-Containing Oxidants
  作者：Anupam Mukherjee、Ramesh B. Dateer、Rupsha Chaudhuri、Sabyasachi Bhunia、Somnath Narayan Karad、Rai-Shung Liu

  DOI：10.1021/ja208150d

  日期：2011.10.5

  We report two viable routes for the 1,2difunctionalization of aminoalkynes using only oxidants. In the presence of a gold catalyst, nitrones enable the oxoamination of aminoalkynes 1 to form 2-aminoamides 2. With a suitable gold catalyst, nitrosobenzenes implement an alkyne/nitroso metathesis of the same substrates to give 2-oxoiminylamides 3. These two novel oxidations also provide 1,2-aminoalcohols with opposite regioselectivity via NaBH4 reduction in situ.