2-azido-2-phenyl-1H-indene-1,3(2H)-dione | 3818-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-azido-2-phenyl-1H-indene-1,3(2H)-dione
• 英文别名: 2-azido-2-phenylindene-1,3-dione
• CAS: 3818-16-4
• 化学式: C₁₅H₉N₃O₂
• 分子量: 263.255
• InChiKey: OIAUTJYWXCWBSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-2-phenyl-1H-indene-1,3(2H)-dione 以43%的产率得到
  参考文献：
  名称：

  BRUVELE, N. R.;GUDRINIETSE, EH. YU., IZV. AN LATVSSR. CEP. XIM., 1984, N 1, 76-79

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-2-苯基茚满-1,3-二酮 在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以84%的产率得到2-azido-2-phenyl-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  Photoinduced α-Cleavage of 2-Azido-2-phenyl-1,3-indandione at Cryogenic Temperatures

  摘要：

  To expand the utility of α-cleavage at cryogenic temperatures, we investigated the photoreactivity of 2-azido-2-phenyl-1,3-indandione (1). EPR spectroscopy revealed that irradiating 1 in 2-methyltetrahydrofuran (mTHF) matrices forms alkylnitrene ³2, which has zero-field splitting parameters (D/hc = 1.5837 cm^-1; E/hc = 0.0039 cm^-1) typical of an alkylnitrene. IR spectroscopy demonstrated that irradiating 1 in argon matrices results in the concurrent formation of ³2, imine 3, benzocyclobutenedione 4, and benzonitrile 5.

  DOI：

  10.1021/acs.orglett.0c02794

文献信息

• Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides
  作者：Bayu Ardiansah、Hiroki Tanimoto、Takenori Tomohiro、Tsumoru Morimoto、Kiyomi Kakiuchi

  DOI：10.1039/d1cc02770k

  日期：——

  Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C–H and C–C bonds was accessible to the one-pot substitution reaction.

  描述了锍离子的施密特反应。一般的伯、仲和叔烷基叠氮化物被转化为相应的羰基或亚胺化合物，而没有任何痕量的活化剂。这种通过 C-H 和 C-C 键的 1,2-迁移发生的键断裂反应可用于一锅取代反应。
• Ring Expansion of 2-Azido-2-phenyl-indan-1,3-dione for the Generation of Heterocyclic Scaffolds
  作者：Fabia Mittendorf、Fabian Mohr、Stefan F. Kirsch

  DOI：10.1021/acs.joc.0c01586

  日期：2020.10.2

  A novel ring expansion based on the readily available 2-azido-2-phenyl-indan-1,3-dione is described. Treatment with primary amines and cesium carbonate in a two-step sequence gives rise to 3-amino-2,3-dihydroisoquinoline-1,4-diones with an unprecedented substitution pattern. The corresponding conversion using amino acid methyl esters leads directly to a novel tricyclic 1,10a-dihydroimidazo-isoquinoline-2

  描述了一种基于容易获得的2-叠氮基-2-苯基-茚满-1,3-二酮的新型环扩环。用伯胺和碳酸铯分两步进行处理，得到具有空前取代模式的3-氨基-2,3-二氢异喹啉-1,4-二酮。据我们所知，使用氨基酸甲酯的相应转化直接导致了新颖的三环1,10a-二氢咪唑基-异喹啉-2,5,10-三酮支架，该结构从未被报道过。
• Photoinduced α-Cleavage of 2-Azido-2-phenyl-1,3-indandione at Cryogenic Temperatures
  作者：Upasana Banerjee、Sujan K. Sarkar、Jeanette A. Krause、William L. Karney、Manabu Abe、Anna D. Gudmundsdottir

  DOI：10.1021/acs.orglett.0c02794

  日期：2020.10.16

  To expand the utility of α-cleavage at cryogenic temperatures, we investigated the photoreactivity of 2-azido-2-phenyl-1,3-indandione (1). EPR spectroscopy revealed that irradiating 1 in 2-methyltetrahydrofuran (mTHF) matrices forms alkylnitrene ³2, which has zero-field splitting parameters (D/hc = 1.5837 cm^-1; E/hc = 0.0039 cm^-1) typical of an alkylnitrene. IR spectroscopy demonstrated that irradiating 1 in argon matrices results in the concurrent formation of ³2, imine 3, benzocyclobutenedione 4, and benzonitrile 5.
• BRUVELE, N. R.;GUDRINIETSE, EH. YU., IZV. AN LATVSSR. CEP. XIM., 1984, N 1, 76-79
  作者：BRUVELE, N. R.、GUDRINIETSE, EH. YU.

  DOI：——

  日期：——