N-(1-oxo-3,4-diphenyl-1H-isochromen-8-yl)acetamide | 1147304-09-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: N-(1-oxo-3,4-diphenyl-1H-isochromen-8-yl)acetamide
• 英文别名: N-(1-oxo-3,4-diphenylisochromen-8-yl)acetamide
• CAS: 1147304-09-3
• 化学式: C₂₃H₁₇NO₃
• 分子量: 355.393
• InChiKey: NZSDXNMFQMRGSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻乙酰氨基苯甲酸 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 silver(I) acetate 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 生成 N-(1-oxo-3,4-diphenyl-1H-isochromen-8-yl)acetamide
  参考文献：
  名称：

  Ruthenium(II) Catalyzed Regiospecific C–H/O–H Annulations of Directing Arenes via Weak Coordination

  摘要：

  Ruthenium(II) catalyzed oxidative CH/OH annulations have been demonstrated using two different directing arenes viz. 2-arylquinolinone and 2-arylbenzoxazinone with internal alkynes. Regiospecific annulations have been observed for both directing arenes via the assistance of weaker carbonyl oxygen in the presence of a stronger nitrogen-directing site. In this substrate-controlled convergent protocol the weaker directing group dictates the annulation path.

  DOI：

  10.1021/acs.orglett.5b02967

文献信息

• The amide C–N bond of isatins as the directing group and the internal oxidant in Ru-catalyzed C–H activation and annulation reactions: access to 8-amido isocoumarins
  作者：Partha Pratim Kaishap、Bipul Sarma、Sanjib Gogoi

  DOI：10.1039/c6cc04461a

  日期：——

  The amide C–N bond of isatins was used as the oxidizing directing group for 4C–H activation and annulation reactions with alkynes.

  吲哚酮的酰胺C-N键被用作氧化定向基团，用于与炔烃进行4C-H活化和环化反应。
• Waste-Free Synthesis of Condensed Heterocyclic Compounds by Rhodium-Catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes
  作者：Masaki Shimizu、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo900396z

  日期：2009.5.1

  of 2-amino- and 2-hydroxybenzoic acids with internal alkynes proceeds efficiently in the presence of a rhodium/copper catalyst system under air to afford the corresponding 8-substituted isocoumarin derivatives, some of which exhibit solid-state fluorescence. Depending on conditions, 4-ethenylcarbazoles can be synthesized selectively from 2-(arylamino)benzoic acids. The oxidative coupling reactions of

  在空气中，在铑/铜催化剂体系的存在下，2-氨基和2-羟基苯甲酸与内部炔烃的直接氧化偶联有效地进行，从而得到相应的8-取代的异香豆素衍生物，其中一些表现出固态荧光。根据条件，可以从2-（芳基氨基）苯甲酸选择性地合成4-乙烯基咔唑。还描述了杂芳烃羧酸以及芳族二酸与炔烃的氧化偶联反应。
• Ruthenium(II) Catalyzed Regiospecific C–H/O–H Annulations of Directing Arenes via Weak Coordination
  作者：Arghya Banerjee、Sourav Kumar Santra、Prakash Ranjan Mohanta、Bhisma K. Patel

  DOI：10.1021/acs.orglett.5b02967

  日期：2015.11.20

  Ruthenium(II) catalyzed oxidative CH/OH annulations have been demonstrated using two different directing arenes viz. 2-arylquinolinone and 2-arylbenzoxazinone with internal alkynes. Regiospecific annulations have been observed for both directing arenes via the assistance of weaker carbonyl oxygen in the presence of a stronger nitrogen-directing site. In this substrate-controlled convergent protocol the weaker directing group dictates the annulation path.