1-(4-chlorophenyl)-2-(phenylamino)ethan-1-ol | 99940-34-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-chlorophenyl)-2-(phenylamino)ethan-1-ol
• 英文别名: 1-(4-chlorophenyl)-2-(phenylamino)ethanol；2-Anilino-1-(4-chlorophenyl)ethanol
• CAS: 99940-34-8
• 化学式: C₁₄H₁₄ClNO
• 分子量: 247.724
• InChiKey: NVCBYZAHNRTUQH-UHFFFAOYSA-N

物化性质

• 沸点：
  434.3±35.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  2

反应信息

• 作为产物：
  描述：

  1-(4-chlorophenyl)-2-(N-trimethylsilyloxyanilino)ethanone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 1-(4-chlorophenyl)-2-(phenylamino)ethan-1-ol
  参考文献：
  名称：

  Synthesis of β-N-Phenylamino Alcohols and α-N-Phenylamino Acids via Reduction of the Adducts of Silyl Enol Ethers and Bis-silyl Ketene Acetals with Nitrosobenzene

  摘要：

  DOI：

  10.1055/s-1985-31177

文献信息

• Synthesis of 1,2-amino alcohols by decarboxylative coupling of amino acid derived α-amino radicals to carbonyl compounds <i>via</i> visible-light photocatalyst in water
  作者：Shulei Pan、Min Jiang、Jinjin Hu、Ruigang Xu、Xiaofei Zeng、Guofu Zhong

  DOI：10.1039/c9gc03470f

  日期：——

  coupling reaction of N-aryl amino acids with aldehydes or ketones for the synthesis of various 1,2-amino alcohols by using water as the solvent at room temperature is described. This protocol is characterised by broad substrate scopes, mild reaction conditions and amenability to gram-scale synthesis, which opens up a simple, mild but effective method to produce 1,2-amino alcohols from readily available

  描述了在室温下用水作为溶剂，N-芳基氨基酸与醛或酮的通用且有效的可见光光氧化还原催化的脱羧自由基偶联反应，用于合成各种1,2-氨基醇。该方案的特点是具有广泛的底物范围，温和的反应条件和对克级合成的适应性，这为从容易获得的起始原料生产1,2-氨基醇提供了一种简单，温和但有效的方法。
• Highly Effective Opening of Epoxides with Aromatic Amines in Presence of β-Cyclodextrin in Water
  作者：Siping Tang、Zhifeng Xu、Junhua Li、Peihong Deng、Lanyong Feng

  DOI：10.14233/ajchem.2018.21260

  日期：——

  guest molecule. β-Cyclodextrin catalyzes chemical reactions by supramolecular catalysis with high efficiency. No investi-gations of ring opening of epoxides with aromatic amines in the presence of β-cyclodextrin in water have been reported. Our earlier study on ester hydrolysis successfully catalyzed by β-cyclodextrin derivatives [21-23] promoted us Highly Effective Opening of Epoxides with Aromatic Amines

  β-氨基醇是合成各种具有生物活性的天然和合成产品（如非天然氨基酸 [1,2] 和手性助剂 [3]）的多功能中间体。制备 β-氨基醇的经典方法包括在升高的温度下在过量的胺中使环氧化物开环 [4]。这些反应伴随着区域选择性差和反应时间长。为了避免这些缺点，最近报道了其他方法，包括使用金属氨化物 [5-7]、金属三氟甲磺酸盐 [8-10]、金属卤化物 [11-14]、有机三氟甲磺酸盐络合物 [15]、铜（II ) 四氟硼酸盐 [16]、离子液体 [17]、磷钼酸-Al2O3 [18]、硫脲 [19] 和 Hβ 沸石 [20]。然而，这些方法中的大多数都涉及使用昂贵的试剂，空气和/或湿度敏感的催化剂、危险的有机溶剂和区域选择性差。鉴于这些局限性，预计将开发出廉价、环境友好且高效的催化剂，用于环氧化物直接与苯胺的开环。环糊精具有疏水腔，通过非共价键与底物形成主客体复合物。络合取决于客体分子的大小、形
• Urushiol derivatives as biomass-based photocatalysts for the transition-metal-free synthesis of 1,2-amino alcohols
  作者：Xiaozhou Huang、Ya-Qing Hu、Cen Zhou、Ying Zheng、Xiao Zhang

  DOI：10.1039/d2gc01410f

  日期：——

  decarboxylative coupling of amino acids with aldehydes. A series of 1,2-amino alcohols are accessed in a transition-metal-free fashion under eco-friendly and redox-neutral conditions. The application of an urushiol-derived film in visible-light photoredox catalysis is also disclosed.

  从可再生和可持续资源中开发催化剂是有机合成的一个重要目标。在这里，我们展示了使用漆酚衍生物作为基于生物质的催化剂，用于可见光诱导的氨基酸与醛的脱羧偶联。在环保和氧化还原中性条件下，可以以无过渡金属的方式获得一系列 1,2-氨基醇。还公开了漆酚衍生薄膜在可见光光氧化还原催化中的应用。
• 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.