1-(2-methoxyphenylamino)-3-phenoxypropan-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-methoxyphenylamino)-3-phenoxypropan-2-ol
• 英文别名: 1-[(2-Methoxyphenyl)amino]-3-phenoxypropan-2-ol；1-(2-methoxyanilino)-3-phenoxypropan-2-ol
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: PEHGANIRNYYRMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基缩水甘油醚 、 邻甲氧基苯胺 在 zinc trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-(2-methoxyphenylamino)-3-phenoxypropan-2-ol
  参考文献：
  名称：

  通过中继环氧化物开放/醇化反应获得四氢喹喔啉的立体收敛，氧化还原中性。

  摘要：

  我们提出了一种经济的催化程序，以高度对映选择性的方式将容易获得的1,2-二氨基苯和末端环氧化物转化为有价值的1,2,3,4-四氢喹喔啉。该过程通过中继锌和铱催化而进行，并从外消旋起始原料中以水为唯一副产物，实现了氧化还原中性和立体收敛性生产有价值的手性杂环。使用可商购的试剂和催化剂以及方便的程序也使该催化方法对实际应用具有吸引力。

  DOI：

  10.1002/anie.201906199

文献信息

• Efficient Synthesis of β‐Amino Alcohols Catalyzed by Niobium Pentachloride: Regioselective Ring Opening of Epoxides with Aromatic Amines
  作者：A. Venkat Narsaiah、D. Sreenu、K. Nagaiah

  DOI：10.1080/00397910600908884

  日期：2006.10.1

  Abstract Epoxides undergo a rapid ring‐opening reaction with aromatic amines catalyzed by niobium pentachloride under mild reaction conditions. All the reactions were carried out at room temperature to afford the corresponding β‐amino alcohols in excellent yields and with high regioselectivity. IICT Communication No. 050916

  摘要 在温和的反应条件下，五氯化铌催化环氧化物与芳香胺发生快速开环反应。所有反应均在室温下进行，以优异的产率和高区域选择性得到相应的 β-氨基醇。IICT通讯第050916号
• 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
• Fe(OH)3 nano solid material: An efficient catalyst for regioselective ring opening of aryloxy epoxide with amines under solvent free condition
  作者：Arpan K. Shah、K. Jeya Prathap、Manish Kumar、Sayed H.R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1016/j.apcata.2013.10.003

  日期：2014.1

  Iron hydroxide-Fe(OH)(3) and iron oxides (Fe3O4 and Fe2O3) were successfully prepared and characterized. These materials were employed as efficient and environmentally benign heterogeneous catalysts for the epoxide ring opening reaction of various alyloxy, terminal and meso epoxides with aromatic and aliphatic amines under solvent free condition at room temperature. Out of these, nano-sized Fe(OH)(3) (IH-1) showed better catalytic activity to give the product beta-amino alcohols in excellent yield (up to similar to 96%) and high regioselectivity in 10-360 min. The catalyst was successfully recycled and reused eight times with no loss in catalytic activity. (C) 2013 Published by Elsevier B.V.
• Highly Efficient Aminolysis of Epoxides Catalyzed by Reusable Zirconyl Triflate, ZrO(OTf)₂
  作者：Majid Moghadam、Shahram Tangestaninejad、Valiollah Mirkhani、Iraj Mohammadpoor-Baltork、Saeedeh Gorjipoor、Parvin Yazdani

  DOI：10.1080/00397910802406729

  日期：2009.1.13

  Efficient ring opening of epoxides with aromatic amines catalyzed by ZrO(OTf)(2) is reported, and the corresponding beta amino (beta-amino acid) alcohols were obtained in high yields in CH3CN as solvent. The reactions were carried out at room temperature and in the presence of only 1.25 mol% of ZrO(OTf)(2). This catalyst can be reused several times without loss of its activity.
• Potassium Dodecatungstocobaltate Trihydrate (K₅CoW₁₂O₄₀ · 3H₂O) as an Efficient Catalyst for Aminolysis of Epoxides
  作者：E. Rafiee、Shahram Tangestaninejad、M. H. Habibi、V. Mirkhani

  DOI：10.1081/scc-200032411

  日期：2004.1.1

  Aminolysis of epoxides using various amines was catalyzed with potassium dodecatungstocobaltate trihydrate in a convenient and efficient method with good selectivities.