2-methyl-4,5-dihydro-2H-benzo[c]azepine-1,3-dione | 1383563-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2-methyl-4,5-dihydro-2H-benzo[c]azepine-1,3-dione
• 英文别名: 2-Methyl-4,5-dihydro-2-benzazepine-1,3-dione
• CAS: 1383563-71-0
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: SBPDIHDNZIYYST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-4,5-dihydro-2H-benzo[c]azepine-1,3-dione 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 14.5h， 生成 3-(4-methoxyphenyl)-2-methyl-4,5-dihydro-3H-2-benzazepin-1-one
  参考文献：
  名称：

  A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework

  摘要：

  A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.

  DOI：

  10.1055/s-0031-1290504
• 作为产物：
  描述：

  N-甲基-2-乙烯基苯甲酰胺 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.5h， 生成 2-methyl-4,5-dihydro-2H-benzo[c]azepine-1,3-dione
  参考文献：
  名称：

  A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework

  摘要：

  A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.

  DOI：

  10.1055/s-0031-1290504

文献信息

• 2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions
  作者：Roberto Frutos-Pedreño、José-Antonio García-López

  DOI：10.1002/adsc.201600224

  日期：2016.8.18

  The synthesis of biologically relevant homophthalimide and 3‐aminoisocoumarin nuclei via palladium‐catalyzed carbonylation of 2‐(2‐iodoaryl)acetamides has been developed. The degree of N‐substitution on the starting amide substrate dictates whether C−N or C−O coupling takes place in the final step of the catalytic cycle giving rise to each type of heterocycle. The introduction of a second C−halogen

  已经开发了通过钯催化的2-（2-碘代芳基）乙酰胺的羰基合成生物相关的邻苯二甲酰亚胺和3-氨基异香豆素核。起始酰胺底物上的N取代程度决定了是在催化循环的最后一步中发生C偶联还是C偶联，从而产生了每种类型的杂环。在起始乙酰胺中引入第二个C-卤素键可进行涉及CH-H活化步骤的催化级联双羰基化反应，从而生成稠合的杂环结构。
• Synthesis and Reactivity of Ortho-Palladated 3-Phenylpropanamides. Insertion of CO, XyNC, and Alkynes into the Pd–C Bond. Synthesis of Seven- and Nine-Membered Palladacycles and Benzazepine- and Benzazonine-Based Heterocycles
  作者：Roberto Frutos-Pedreño、Pablo González-Herrero、José Vicente、Peter G. Jones

  DOI：10.1021/om4000192

  日期：2013.3.25

  Aryl palladium complexes [PdC6H4(CH2)2C(O)NRR′)-2}I(tmeda)] [NRR′ = NH2 (1a), NHMe (1b), NMe2 (1c); tmeda = N,N,N′,N′-tetramethylethylenediamine] are prepared by oxidative addition of the corresponding 3-(2-iodophenyl)propanamides to “Pd(dba)2” ([Pd2(dba)3]·dba; dba = dibenzylideneacetone) in the presence of tmeda. The cationic seven-membered palladacycles [Pdκ2C,O-C6H4(CH2)2C(O)NRR′)-2}(tmeda)]TfO

  芳基钯络合物[Pd C 6 H 4（CH 2）2 C（O）NRR'）-2} I（tmeda）] [NRR'= NH 2（1a），NHMe（1b），NMe 2（1c） ; 通过将相应的3-（2-碘苯基）丙酰胺氧化加成到“ Pd（dba）2 ”（[Pd 2（dba）3 ]·dba中，制备tmeda ＝N，N，N ′，N′-四甲基乙二胺）。在tmeda存在下dba =二亚苄基丙酮）。阳离子7元钯环[钯κ 2 Ç，Ò-C 6 H 4（CH 2）2 C（O）NRR'）-2}（tmeda）] TfO（2a – c）是通过1a – c与AgTfO反应获得的。类型[钯κ的中性配合物酰胺化物2 Ç，Ñ -C 6 ħ 4（CH 2）2 C（O）NR）-2}（TMEDA）] [R = H（图3a）中，Me（图3b）]通过用KO t Bu使1a或1b中的酰胺官能团去质子化而获得。1a的反应在室温下用CO生成稳定的酰基衍生物[Pd
• A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework
  作者：Axel Couture、Stéphane Lebrun、Eric Deniau、Pierre Grandclaudon

  DOI：10.1055/s-0031-1290504

  日期：2012.5

  A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.