2'-Acetyldiacetanilide | 150370-71-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-Acetyldiacetanilide
• 英文别名: o-(N,N-Diacylamino)acetophenone；N-acetyl-N-(2-acetylphenyl)acetamide；N-(2-acetyl-phenyl)-diacetamide；N-(2-Acetyl-phenyl)-diacetamid
• CAS: 150370-71-1
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: VOKSGTDEACDSAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-Acetyldiacetanilide 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到N-(2-乙酰苯基)乙酰胺
  参考文献：
  名称：

  Oxidation of N-Acylindoles by Dimethyldioxirane and Singlet Oxygen: Substituent Effects on Thermally Persistent Indole Epoxides and Dioxetanes

  摘要：

  Photooxygenation of the N-acylindoles 1a-d afforded the labile indole dioxetanes 2 and the relatively stable allylic hydroperoxides 3. The dioxetanes 2a,c,d were sufficiently stable for isolation and spectral characterization. Additionally, they were characterized by chemical transformations, namely reduction to the indole epoxides 5 by dimethyl sulfide, acid-catalyzed rearrangement to allylic hydroperoxides 3c,d, and thermolysis to the cleavage products 4. Oxidation of the N-acylindoles I with dimethyldioxirane afforded the epoxides 5, which were characterized on the basis of their spectral data and chemical transformations to the 2-indolinones 6 and 2-methyleneindoline 7. These decomposition products (except 7e) were fully characterized. The stability of the epoxides 5 depended on the substitution type, i.e., the carbazole epoxide 5c decomposed already at temperatures above ca. -50 degrees C, whereas the cyclopentindole epoxide 5b was stable at 20 degrees C for days. The latter was unequivocally characterized by X-ray analysis.

  DOI：

  10.1021/jo00089a016
• 作为产物：
  描述：

  1-(2,3-二甲基吲哚-1-基)乙酮 在 亚甲兰 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 10.0h， 以68%的产率得到2'-Acetyldiacetanilide
  参考文献：
  名称：

  亚甲基蓝催化的N-羰基化吲哚的氧化裂解

  摘要：

  作为特别主题“现代自由基方法及其在合成中的战略应用”的一部分发布 抽象的 据报道，缺电子吲哚的可见光介导的氧化裂解的发展。亚甲基蓝是有效的催化剂，该转化显示出较宽的底物范围。在温和的反应条件下可以很好地容纳各种官能团。通过密度泛函理论和马库斯理论计算研究了光介导的单电子转移和氧化裂解机理。 据报道，缺电子吲哚的可见光介导的氧化裂解的发展。亚甲基蓝是有效的催化剂，该转化显示出较宽的底物范围。在温和的反应条件下可以很好地容纳各种官能团。通过密度泛函理论和马库斯理论计算研究了光介导的单电子转移和氧化裂解机理。

  DOI：

  10.1055/s-0036-1592006

文献信息

• Oxidation of indoles by singlet oxygen and dimethyldioxirane: Isolation of indole dioxetanes and epoxides by stabilization through nitrogen acylation
  作者：Waldemar Adam、Michael Ahrweiler、Markus Sauter、Bernd Schmiedeskamp

  DOI：10.1016/s0040-4039(00)73964-5

  日期：1993.8

  through N-acylation allowed the isolation of the labile indole dioxetanes 2, which were transformed by dimethyl sulfide deoxygenation to the corresponding indole epoxides 5; the latter were also independently prepared by dimethyldioxirane oxidation.

  通过N-酰化作用的稳定作用可以分离出不稳定的吲哚二氧杂环丁烷2，其通过二甲基硫醚的脱氧作用转化为相应的吲哚环氧化物5。后者也通过二甲基二环氧乙烷氧化独立制备。
• Atkinson et al., Journal of the Chemical Society, 1954, p. 165,170
  作者：Atkinson et al.

  DOI：——

  日期：——
• 1,2-Dioxetane formation in photooxygenation of N-acylated indole derivatives
  作者：Xiaojun Zhang、Christopher S. Foote

  DOI：10.1021/jo00072a042

  日期：1993.9

  Eight N-acylated indole derivatives (1a-h) react with singlet oxygen at low temperature (-5 to -78-degrees-C) in methanol-d4 or methanol-d4-methylene chloride-d2 to afford 1,2-dioxetanes 2a-h, whose structures are characterized by low-temperature C-13 NMR and H-1 NMR spectra and chemical transformations. These strained 1,2-dioxetanes decompose smoothly and exclusively to dicarbonyl cleavage products 3a-h upon warming to room temperature.
• Oxidation of N-Acylindoles by Dimethyldioxirane and Singlet Oxygen: Substituent Effects on Thermally Persistent Indole Epoxides and Dioxetanes
  作者：Waldemar Adam、Michael Ahrweiler、Karl Peters、Bernd Schmiedeskamp

  DOI：10.1021/jo00089a016

  日期：1994.5

  Photooxygenation of the N-acylindoles 1a-d afforded the labile indole dioxetanes 2 and the relatively stable allylic hydroperoxides 3. The dioxetanes 2a,c,d were sufficiently stable for isolation and spectral characterization. Additionally, they were characterized by chemical transformations, namely reduction to the indole epoxides 5 by dimethyl sulfide, acid-catalyzed rearrangement to allylic hydroperoxides 3c,d, and thermolysis to the cleavage products 4. Oxidation of the N-acylindoles I with dimethyldioxirane afforded the epoxides 5, which were characterized on the basis of their spectral data and chemical transformations to the 2-indolinones 6 and 2-methyleneindoline 7. These decomposition products (except 7e) were fully characterized. The stability of the epoxides 5 depended on the substitution type, i.e., the carbazole epoxide 5c decomposed already at temperatures above ca. -50 degrees C, whereas the cyclopentindole epoxide 5b was stable at 20 degrees C for days. The latter was unequivocally characterized by X-ray analysis.
• Methylene Blue-Catalyzed Oxidative Cleavage of N-Carbonylated Indoles
  作者：Peng Liu、Ting Wang、Kui Wu、Cheng Fang、Sarbjeet Kaur

  DOI：10.1055/s-0036-1592006

  日期：2018.8

  The development of a visible-light-mediated oxidative cleavage of electron-deficient indoles is reported. Methylene blue serves as an effective catalyst and the transformation shows a broad substrate scope. A variety of functional groups are well accommodated in the mild reaction conditions. The photo-mediated single electron transfer and oxidative cleavage mechanisms were investigated via density functional

  作为特别主题“现代自由基方法及其在合成中的战略应用”的一部分发布 抽象的 据报道，缺电子吲哚的可见光介导的氧化裂解的发展。亚甲基蓝是有效的催化剂，该转化显示出较宽的底物范围。在温和的反应条件下可以很好地容纳各种官能团。通过密度泛函理论和马库斯理论计算研究了光介导的单电子转移和氧化裂解机理。 据报道，缺电子吲哚的可见光介导的氧化裂解的发展。亚甲基蓝是有效的催化剂，该转化显示出较宽的底物范围。在温和的反应条件下可以很好地容纳各种官能团。通过密度泛函理论和马库斯理论计算研究了光介导的单电子转移和氧化裂解机理。