10b-Hydroxy-1,2,3,4-tetrahydropyrido[2,1-a]isoindol-6-one | 88892-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 10b-Hydroxy-1,2,3,4-tetrahydropyrido[2,1-a]isoindol-6-one
• 英文别名: 10b-hydroxy-1,2,3,4-tetrahydropyrido[2,1-a]isoindol-6-one
• CAS: 88892-69-7
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: PZNIEYNEBGQMLC-UHFFFAOYSA-N

物化性质

• 沸点：
  414.1±44.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 在 samarium diiodide 、 tris(dibenzoylmethano)iron(III) 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成 10b-Hydroxy-1,2,3,4-tetrahydropyrido[2,1-a]isoindol-6-one
  参考文献：
  名称：

  N-碘代烷基环状酰亚胺的还原环化成二碘化sa诱导的氮稠合多环酰​​胺

  摘要：

  已经研究了SmI 2促进的在酰亚胺氮上具有3-碘丙基或4-碘丁基的环状酰亚胺的环化，以构建氮稠合的多环酰胺。

  DOI：

  10.1016/0040-4039(96)00374-7

文献信息

• Synthesis of Medium- and Large-Ring Compounds Initiated by Photochemical Decarboxylation of ω-Phthalimidoalkanoates
  作者：Axel G. Griesbeck、Andreas Henz、Wolfgang Kramer、Johann Lex、Frank Nerowski、Michael Oelgemöller、Karl Peters、Eva-Maria Peters

  DOI：10.1002/hlca.19970800324

  日期：1997.5.12

  reaction initiated by intramolecular photo electron transfer is described. Ring sizes available by this method span from 4 (benzazepine-1,5-dione 7) to 26 (cyclodipeptide 26e). Ground-state template formation is proposed as the explanation for the high efficiency of this reaction and for the decrease in reactivity in the presence of organic bases instead of metal carbonates. The crucial step in this

  描述了使用由分子内光电子转移引发的三重态敏化的光脱羧反应，由ω-邻苯二甲酰亚胺基链烷酸酯合成多种羟基内酰胺。通过该方法可获得的环的大小为4（苯并ze庚因-1，5-二酮7）至26（环二肽26e）。提出了基态模板形成作为该反应的高效率和在存在有机碱而不是金属碳酸盐的情况下反应性降低的解释。在该大环化反应中的关键步骤似乎是中间的酮基放射状质子的质子化（方案4）。研究的间隔基是烷基链（C 3 -C 11：5c-h，11a，12），醚（16、18），酯（20、22）和酰胺（26a-f）键。在检测限内，未观察到二聚体（=脱羧偶联）产物，表明分子间光电子转移与分子间光电子转移具有高度优先性。与可比的单线态反应相反，C，C自由基组合步骤以低的立体选择性进行（参见产品11和12）。除了内酯22以外，所有产物在光解条件下都是稳定的。的延长照射22导致螺形成的化合物23，可能通过中间体酰基甜菜碱甜菜碱（方案8）
• A Solvent Effect That Influences the Preparative Utility of <i>N</i>-(Silylalkyl)phthalimide and <i>N</i>-(Silylalkyl)maleimide Photochemistry
  作者：Ung Chan Yoon、Sun Wha Oh、Soo Min Lee、Sung Ju Cho、Janet Gamlin、Patrick S. Mariano

  DOI：10.1021/jo990087a

  日期：1999.6.1

  The photochemistry of selected N-silylalkyl-substituted phthalimides and maleimides has been investigated with the aim of exploring the generality and preparative consequences of an intriguing solvent effect on excited-state reaction chemoselectivities and quantum efficiencies. An example of this effect is found in the photochemistry of N-[(trimethylsilyl)butyl]phthalimide 10, where irradiation in MeCN leads to production of a mixture of four products that arise by excited-state intramolecular hydrogen-atom abstraction. In contrast, the benzoindolizidine 15 is the sole product produced by a single electron transfer (SET)-desilylation pathway upon irradiation of 10 in 35% H2O-MeCN. Another example of this solvent effect is found in the photochemistry of the N-silylpropyl-maleimide 17. Irradiation in MeCN results in the production of the 2+2-dimer 19 whereas the pyrrolizidine 18 is generated exclusively by irradiation of 17 in 35% H2O-MeCN. The results of fluorescence and triplet sensitization experiments suggest that the solvent effect has multiple sources including the control of the nature, reactivity, and intrinsic lifetimes of singlet and triplet excited states of the phthalimide and maleimide systems. The exploratory studies have clearly demonstrated the generality of this solvent effect and how it can be used to enhance the preparative utility of the photochemistry of N-(silylalkyl)phthalimides and N-(silylalkyl)maleimides.
• Griesbeck, Axel G., Chimia, 1998, vol. 52, # 6, p. 272 - 283
  作者：Griesbeck, Axel G.

  DOI：——

  日期：——
• Griesbeck, Axel G.; Henz, Andreas; Peters, Karl, Angewandte Chemie, 1995, vol. 107, # 4, p. 498 - 500
  作者：Griesbeck, Axel G.、Henz, Andreas、Peters, Karl、Peters, Eva-Maria、Schnering, Hans Georg von

  DOI：——

  日期：——
• Reductive cyclization of N-iodoalkyl cyclic imides to nitrogen-fused polycyclic amides induced by samarium diiodide
  作者：Deok-Chan Ha、Chang-Soo Yun、Eunsun Yu

  DOI：10.1016/0040-4039(96)00374-7

  日期：1996.4

  SmI2-promoted cyclizations of cyclic imides having 3-iodopropyl or 4-iodobutyl groups on the imide nitrogen have been studied for construction of nitrogen-fused polycyclic amides.

  已经研究了SmI 2促进的在酰亚胺氮上具有3-碘丙基或4-碘丁基的环状酰亚胺的环化，以构建氮稠合的多环酰胺。