N,N-二乙基-3-(2-羟基苯基)-3-氧代丙酰胺 | 211449-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N,N-二乙基-3-(2-羟基苯基)-3-氧代丙酰胺
• 英文名称: N,N-diethyl-3-(2-hydroxyphenyl)-3-oxopropanamide
• CAS: 211449-34-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: DVQWBFVBAGLODG-UHFFFAOYSA-N

物化性质

• 沸点：
  387.7±22.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二乙基-3-(2-羟基苯基)-3-氧代丙酰胺 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以89%的产率得到4-羟基香豆素
  参考文献：
  名称：

  Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

  摘要：

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00977-0
• 作为产物：
  描述：

  methyl β-oxo-2-(phenylmethoxy)benzenepropanoate 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 生成 N,N-二乙基-3-(2-羟基苯基)-3-氧代丙酰胺
  参考文献：
  名称：

  通过苯碘（III）双（三氟乙酸盐）（PIFA）介导的级联氧化C-O和C-C键形成合成呋喃呋喃并吲哚

  摘要：

  仅使用苯基碘（III）双（三氟乙酸盐）（PIFA）的高价碘试剂处理后，即可将3-（2-羟基苯基）-3-氧代-N-苯基丙酰胺及其一系列衍生物方便地转换为一类在温和条件下未记录的螺呋喃氧吲哚。对照实验提供的证据表明，该螺环化过程包括级联氧化反应，该级联氧化反应涉及先于C-C键形成C-O键。

  DOI：

  10.1002/adsc.201701635

文献信息

• A Baker–Venkataraman retro-Claisen cascade delivers a novel alkyl migration process for the synthesis of amides
  作者：Dana Ameen、Timothy J. Snape

  DOI：10.1016/j.tetlet.2015.02.077

  日期：2015.4

  A simple extension of the carbamoyl Baker-Venkataraman rearrangement has been developed. If residual water in the reaction is not strictly excluded a Baker-Venkataraman retro-Claisen cascade takes place, giving amide products, in which an alkyl group apparently migrates between two functionalities of the substrate. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Spirofurooxindoles via Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Cascade Oxidative C−O and C−C Bond Formation
  作者：Desong Sun、Xiaoyuan Zhao、Bobo Zhang、Ying Cong、Xintong Wan、Mingmai Bao、Xue Zhao、Bing Li、Daisy Zhang-Negrerie、Yunfei Du

  DOI：10.1002/adsc.201701635

  日期：2018.4.17

  Upon treatment with solely a hypervalent iodine reagent of phenyliodine(III) bis(trifluoroacetate) (PIFA), 3‐(2‐hydroxyphenyl)‐3‐oxo‐N‐phenyl propanamides and a series of its derivatives were conveniently converted to a class of undocumented spirofurooxindoles under mild conditions. Control experiments provided evidence that this spirocyclization process encompassed a cascade oxidative reactions involving

  仅使用苯基碘（III）双（三氟乙酸盐）（PIFA）的高价碘试剂处理后，即可将3-（2-羟基苯基）-3-氧代-N-苯基丙酰胺及其一系列衍生物方便地转换为一类在温和条件下未记录的螺呋喃氧吲哚。对照实验提供的证据表明，该螺环化过程包括级联氧化反应，该级联氧化反应涉及先于C-C键形成C-O键。
• Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins
  作者：Alexey V. Kalinin、Alcides J.M. da Silva、Claudio C. Lopes、Rosangela S.C. Lopes、Victor Snieckus

  DOI：10.1016/s0040-4039(98)00977-0

  日期：1998.7

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.