5-methyl-3-oxo-N-phenylhexanamide | 96649-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methyl-3-oxo-N-phenylhexanamide
• CAS: 96649-98-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: MVTLUILJLOMIKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-3-oxo-N-phenylhexanamide 在 硫酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 3.2h， 生成 3-hydroxy-4-isobutylquinolin-2(1H)-one
  参考文献：
  名称：

  One-Pot Synthesis of 3-Hydroxyquinolin-2(1H)-ones from N-Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization

  摘要：

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.

  DOI：

  10.1021/jo400541s
• 作为产物：
  描述：

  tert-butyl (2-((6-methyl-4-oxo-3-(phenylcarbamoyl)hept-2-en-2-yl)amino)ethyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以93%的产率得到5-methyl-3-oxo-N-phenylhexanamide
  参考文献：
  名称：

  基于烯胺的多米诺策略用于乙酰乙酰胺的 C-酰化/脱乙酰：β-酮酰胺的实际合成

  摘要：

  描述了乙酰乙酰胺的 C-酰化/脱乙酰化的实用三步路线。乙酰乙酰胺与 Boc 单保护乙二胺的初始烯化提供 β-烯氨基酰胺，其在 α-碳上以优异的选择性酰化。C-酰化衍生物在酸性介质中发生多米诺断裂，得到相应的α-酮酰胺，并伴随有 2-甲基-4,5-二氢-1H-咪唑。

  DOI：

  10.1055/s-0029-1219836

文献信息

• Phosphine‐Catalyzed Activation of Vinylcyclopropanes: Rearrangement of Vinylcyclopropylketones to Cycloheptenones
  作者：Jun Wu、Yuhai Tang、Wen Wei、Yong Wu、Yang Li、Junjie Zhang、Yuansuo Zheng、Silong Xu

  DOI：10.1002/anie.201800555

  日期：2018.5.22

  We report a phosphine‐catalyzed activation of electron‐deficient vinylcyclopropanes (VCPs) to generate an ambident C5 synthon that is poised to undergo consecutive reactions. The utility of the activation is demonstrated in a phosphine‐catalyzed rearrangement of vinylcyclopropylketones to cycloheptenones in good yields with a broad substrate scope. Mechanistic investigations support a stepwise process

  我们报告了磷缺乏电子的乙烯基环丙烷（VCP）的膦催化活化，以生成环境温和的C 5合子，准备进行连续反应。该活化的效用在膦催化的乙烯基环丙基酮重排成环庚烯的过程中得到了证明，具有良好的收率，具有广泛的底物范围。机械调查支持一个循序渐进的过程，其包括同合物另外，水辅助质子转移，和7-内切-trig小号Ñ 2'环闭合。
• Fusco,R. et al., Gazzetta Chimica Italiana, 1962, vol. 92, p. 1040 - 1061
  作者：Fusco,R. et al.

  DOI：——

  日期：——
• One-Pot Synthesis of 3-Hydroxyquinolin-2(1<i>H</i>)-ones from <i>N-</i>Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization
  作者：Yucheng Yuan、Rui Yang、Daisy Zhang-Negrerie、Junwei Wang、Yunfei Du、Kang Zhao

  DOI：10.1021/jo400541s

  日期：2013.6.7

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.
• Enamine-Based Domino Strategy for C-Acylation/Deacetylation of Acetoacetamides: A Practical Synthesis of β-Keto Amides
  作者：Plamen Angelov

  DOI：10.1055/s-0029-1219836

  日期：2010.5

  A practical three-step route for C-acylation/deacetylation of acetoacetamides is described. Initial enamination of the acetoacetamides with Boc-monoprotected ethylenediamine provides β-enamino amides, which are acylated at the α-carbon with excellent selectivity. The C-acylated derivatives undergo domino fragmentation in acidic media to give the corresponding α-Keto amides accompanied by 2-methyl-4

  描述了乙酰乙酰胺的 C-酰化/脱乙酰化的实用三步路线。乙酰乙酰胺与 Boc 单保护乙二胺的初始烯化提供 β-烯氨基酰胺，其在 α-碳上以优异的选择性酰化。C-酰化衍生物在酸性介质中发生多米诺断裂，得到相应的α-酮酰胺，并伴随有 2-甲基-4,5-二氢-1H-咪唑。