N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide | 391609-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide
• 英文别名: N-benzyl-2-(4-hydroxy-3-methoxyphenyl)ethylamide；Benzenepropanamide, 4-hydroxy-3-methoxy-N-(phenylmethyl)-；N-benzyl-3-(4-hydroxy-3-methoxyphenyl)propanamide
• CAS: 391609-32-8
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: QDETYVJYSRBZKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以41%的产率得到N-benzyl-3-(3,4-dihydroxyphenyl)-propionamide
  参考文献：
  名称：

  A Stabilized Formulation of IBX (SIBX) for Safe Oxidation Reactions Including a New Oxidative Demethylation of Phenolic Methyl Aryl Ethers

  摘要：

  graphicsSIBX is a nonexplosive formulation of IBX that can be used as a suspension in a variety of standard organic solvents such as refluxing EtOAc and THF to oxidize safely alcohols into aidehydes and ketones. The use of hot THF is limited to the oxidation of allylic and benzylic alcohols. Most yields are comparable to those obtained with IBX or DMIP. SIBX can also be used to perform oxygenative demethylation of 2-methoxyarenols into orthoquinones and catechols.

  DOI：

  10.1021/ol0349965
• 作为产物：
  描述：

  4-羟基-3-甲氧基-苯丙酸乙酯 、 苄胺 在 4 A molecular sieve 作用下， 反应 3.0h， 以87%的产率得到N-benzyl-3-(4-hydroxy-3-methoxyphenyl)-propionamide
  参考文献：
  名称：

  碘（III）介导的氮系邻苯二甲酸邻苯二酚乙酸酯的生成，用于构建氧化的吲哚，喹啉和菲啶生物碱基序。

  摘要：

  官能化的吲哚和喹啉衍生物可以方便地由氮系的2-甲氧基苯酚经二碘苯基碘（III）介导的氧化乙酰氧基化，然后由氟化物或碱引起的分子内亲核加成反应制备。考虑到有时在原位观察到的邻苯二甲酸邻苯二酚中间体重排成乙酸对苯二酚乙酸酯，进一步讨论了该区域选择性迈克尔型添加步骤。本文描述了该方法在功能化菲啶的合成中的应用及其在构建多加氧的茄基型生物碱类骨架中的潜力。

  DOI：

  10.1021/jo020010d

文献信息

• Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation
  作者：Stéphane Quideau、Laurent Pouységu、Anne-Virginie Avellan、Daniel K Whelligan、Matthew A Looney

  DOI：10.1016/s0040-4039(01)01514-3

  日期：2001.10

  Nitrogen-tethered 2-methoxyphenols are conveniently dearomatized into synthetically useful orthoquinol acetates by treatment with phenyliodine(III) diacetate in methylene chloride at low temperature. Subsequent fluoride- or base-induce intramolecular nucleophilic addition reactions furnish indole and quinoline derivatives. The potential of this methodology for the synthesis or a functionalized lycorine-type alkaloid skeleton is introduced here. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A Stabilized Formulation of IBX (SIBX) for Safe Oxidation Reactions Including a New Oxidative Demethylation of Phenolic Methyl Aryl Ethers
  作者：Aurélie Ozanne、Laurent Pouységu、Dominique Depernet、Bruno François、Stéphane Quideau

  DOI：10.1021/ol0349965

  日期：2003.8.1

  graphicsSIBX is a nonexplosive formulation of IBX that can be used as a suspension in a variety of standard organic solvents such as refluxing EtOAc and THF to oxidize safely alcohols into aidehydes and ketones. The use of hot THF is limited to the oxidation of allylic and benzylic alcohols. Most yields are comparable to those obtained with IBX or DMIP. SIBX can also be used to perform oxygenative demethylation of 2-methoxyarenols into orthoquinones and catechols.
• Iodine(III)-Mediated Generation of Nitrogen-Tethered Orthoquinol Acetates for the Construction of Oxygenated Indole, Quinoline, and Phenanthridine Alkaloid Motifs
  作者：Laurent Pouységu、Anne-Virginie Avellan、Stéphane Quideau

  DOI：10.1021/jo020010d

  日期：2002.5.1

  Functionalized indole and quinoline derivatives are conveniently prepared from nitrogen-tethered 2-methoxyphenols via phenyliodine(III) diacetate mediated oxidative acetoxylation, followed by a fluoride- or base-induced intramolecular nucleophilic addition reaction. This regioselective Michael-type addition step is further discussed in view of the rearrangement of orthoquinol acetate intermediates

  官能化的吲哚和喹啉衍生物可以方便地由氮系的2-甲氧基苯酚经二碘苯基碘（III）介导的氧化乙酰氧基化，然后由氟化物或碱引起的分子内亲核加成反应制备。考虑到有时在原位观察到的邻苯二甲酸邻苯二酚中间体重排成乙酸对苯二酚乙酸酯，进一步讨论了该区域选择性迈克尔型添加步骤。本文描述了该方法在功能化菲啶的合成中的应用及其在构建多加氧的茄基型生物碱类骨架中的潜力。