8,8a-Dihydro-1H-azeto[1,2-a]indol-2-one | 113655-80-4

• 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: 8,8a-Dihydro-1H-azeto[1,2-a]indol-2-one
• CAS: 113655-80-4
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: ONWOLEXXBALDNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚-2-乙酸乙酯 在 盐酸 、 硼烷 、 tris(1,3-dihydro-2-oxobenzoxazolin-3-yl) phosphine oxide 、 三乙胺 、 三甲胺 作用下， 以 乙腈 、 三氟乙酸 为溶剂， 生成 8,8a-Dihydro-1H-azeto[1,2-a]indol-2-one
  参考文献：
  名称：

  吲哚-2-乙酸乙酯中的苯并卡培南

  摘要：

  所述benzocarbapenem 1已经准备TROM乙基还原吲哚-2-乙酸酯，水解醇酯和环化。甲基取代的碳青霉烯12，13和14也已制备。乙基组成的氢化Ñ -BOC-吲哚-2- proparioate 5是非对映选择性。

  DOI：

  10.1016/0040-4039(95)01796-k

文献信息

• Active-Copper-Promoted Expeditious N-Arylations in Aqueous Media under Microwave Irradiation
  作者：Lal Yadav、Beerendra Yadav、Vijai Rai

  DOI：10.1055/s-2006-942369

  日期：2006.6

  Active-copper-promoted mild and expeditious N-arylations of amines, amides, imides, and β-lactams with aryl halides under microwave irradiation conditions are reported. These reactions can be performed at 85-90 °C in aqueous media as well as under solvent-free conditions to give good yields. However, under solvent-free conditions, lower yields are obtained.

  报道了在微波辐射条件下，活性铜催化下温和迅速的胺、酰胺、酰亚胺和β-内酰胺与芳基卤化物的N-芳基化反应。这些反应可以在85-90°C的水相中或无溶剂条件下进行，并能获得良好的产率。然而，在无溶剂条件下，产率较低。
• Benzocarbapenems from indoles 1
  作者：Steven Coulton、Thomas L. Gilchrist、Keith Graham

  DOI：10.1039/a800278i

  日期：——

  The 8,8a-dihydroazeto[1,2-a]indol-2(1H)-ones (benzocarbapenems) 1a, 16, 17, 22, 27, 35 and 36 have been prepared by cyclodehydration of the corresponding β-amino acids, these amino acids being obtained by reduction of the analogous 2-substituted or 2,7-disubstituted indoles. The hydroxy group of compound 36 is designed to mimic the carboxylic acid function of the carbapenems on the basis of molecular modelling. The azetidinones 1a and 27, which are unsubstituted at the methylene group of the four-membered ring, are unstable and highly susceptible to ring opening by nucleophiles but the compounds 22, 35 and 36 with two methyl substituents at this position are much more stable. The carbonyl stretching frequency in the IR is close to 1770 cm–1 for all the azetidinones except the phenol 36 for which the absorption is at 1735 cm–1. An X-ray crystal structure of compound 36 is reported.

  8,8a-二氢氮杂环[1,2-a]吲哚-2(1H)-酮（苯并卡培南）1a、16、17、22、27、35和36是通过环脱水反应制备的，其前体为相应的β-氨基酸，这些氨基酸通过还原相应的2-取代或2,7-双取代吲哚获得。化合物36的羟基设计旨在模拟卡培南的羧酸功能，这是基于分子模型的结果。未取代四元环亚甲基的氮杂环酮1a和27不稳定，易受亲核试剂开环，但在该位置具有两个甲基取代基的化合物22、35和36则更为稳定。除了酚类化合物36的吸收频率在1735 cm–1外，所有氮杂环酮的羰基伸缩频率在红外光谱中都接近1770 cm–1。报告了化合物36的X射线晶体结构。
• Joyeau, Roger; Yadav, Lal D. S.; Wakselman, Michel, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1899 - 1908
  作者：Joyeau, Roger、Yadav, Lal D. S.、Wakselman, Michel

  DOI：——

  日期：——
• JOYEAU, ROGER;YADAY, LAL D. S.;WAKSELMAN, MICHEL, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 9, 1899-1907
  作者：JOYEAU, ROGER、YADAY, LAL D. S.、WAKSELMAN, MICHEL

  DOI：——

  日期：——
• Benzocarbapenems from ethyl indole-2-acetate
  作者：Thomas L. Gilchrist、Keith Graham、Steven Coulton

  DOI：10.1016/0040-4039(95)01796-k

  日期：1995.11

  The benzocarbapenem 1 has been prepared trom ethyl indole-2-acetate by reduction, hydrolysis ol the ester and cyclisation. The methyl substituted carbapenems 12, 13 and 14 have also been prepared. The hydrogenation of ethyl N-BOC-indole-2-proparioate 5 is diastereoselective.

  所述benzocarbapenem 1已经准备TROM乙基还原吲哚-2-乙酸酯，水解醇酯和环化。甲基取代的碳青霉烯12，13和14也已制备。乙基组成的氢化Ñ -BOC-吲哚-2- proparioate 5是非对映选择性。