5,7-二硝基吲哚啉 | 67932-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5,7-二硝基吲哚啉
• 英文名称: 5,7-dinitroindoline
• 英文别名: 5,7-dinitro-2,3-dihydro-1H-indole
• CAS: 67932-53-0
• 化学式: C₈H₇N₃O₄
• 分子量: 209.161
• InChiKey: IQBPCKCYMCICBK-UHFFFAOYSA-N

物化性质

• 熔点：
  252-254 °C(Solv: ethanol (64-17-5))
• 沸点：
  373.1±42.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5,7-二硝基吲哚啉 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1-(3-(methoxycarbonyl)propionyl)-5,7-dinitroindoline
  参考文献：
  名称：

  中性条件下胺的光化学酰化制备仲胺和叔胺

  摘要：

  报道了一种通过光激活N-酰基-5,7-二硝基吲哚啉实现胺的平滑中性酰化反应，形成酰胺的方法。改进的硝基吲哚啉酰化反应使得N-酰基硝基吲哚啉的制备变得方便。这一反应还实现了光激活过程中释放的硝基吲哚啉的循环利用。

  DOI：

  10.1055/s-2001-18760
• 作为产物：
  描述：

  N-乙酰基吲哚啉 在 sodium nitrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 三氟乙酸 为溶剂， 反应 23.0h， 生成 5,7-二硝基吲哚啉
  参考文献：
  名称：

  Photochemical Protection of Amines with Cbz and Fmoc Groups

  摘要：

  The photochemical conversion of amines into carbamates was achieved using N-Cbz- N-Fmoc-, and N-Boc-5,7-dinitroindolines. This reaction allows the protection of amines in neutral medium. Primary and unhindered secondary amines were protected to yield their benzyloxycarbonyl- and 9-fluorenylmethoxycarbonyl derivatives efficiently, whereas bulky amines or anilines gave low yields or no product. On the other hand, the formation of N-Boc compounds, although possible, proceeded only with low yields.

  DOI：

  10.1021/jo026581n

文献信息

• Photoacylation of Alcohols in Neutral Medium
  作者：Jean-Luc Débieux、Anne Cosandey、Céline Helgen、Christian G. Bochet

  DOI：10.1002/ejoc.200600790

  日期：2007.5

  We report here conditions which allow the photoacylation of primary, secondary and tertiary alcohols with N-acetyl-5,7-dinitroindoline under exceptionally mild conditions, at wavelengths harmless to most functional groups, including otherwise photosensitive ones. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  我们在这里报告了允许伯醇、仲醇和叔醇与 N-乙酰基-5,7-二硝基二氢吲哚在异常温和的条件下，在对大多数官能团无害的波长下光酰化的条件，包括其他光敏的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Light-Sensitive Protecting Groups for Amines and Alcohols: The Photosolvolysis of N-Substituted 7-Nitroindolines
  作者：Alfred Hassner、Diana Yagudayev、Tarun Pradhan、Abraham Nudelman、Boaz Amit

  DOI：10.1055/s-2007-985580

  日期：2007.9

  Representative examples of primary and secondary amines were protected as urea derivatives 4 of 5-bromo-7-nitro-indoline and even more efficiently as ureas 8 derived from 5,7-di-nitroindoline, via high-yield reactions with carbamoyl chlorides 3 and 7, respectively. Deprotection of 4 or 8 was achieved in high yields by UV irradiation at room temperature in Pyrex vessels under neutral conditions and

  伯胺和仲胺的代表性例子被保护为 5-溴-7-硝基二氢吲哚的脲衍生物 4，甚至更有效地作为衍生自 5,7-二硝基二氢吲哚的脲 8，通过与氨基甲酰氯 3 和7、分别。4 或 8 的脱保护是通过在室温下在 Pyrex 容器中在中性条件下和排除空气中进行紫外线照射来实现的。以类似的方式，二硝基二氢吲哚用作醇类和酚类的保护基团；衍生的氨基甲酸酯5和9同样可以以高产率光化学脱保护。
• The Mechanism of Photoinduced Acylation of Amines by <i>N</i>-Acyl-5,7-dinitroindoline as Determined by Time-Resolved Infrared Spectroscopy
  作者：Andrew D. Cohen、Céline Helgen、Christian G. Bochet、John P. Toscano

  DOI：10.1021/ol050670f

  日期：2005.7.1

  [reaction: see text] The photochemistry of N-acyl-5,7-dinitroindoline (1) was studied in acetonitrile using nanosecond time-resolved infrared (TRIR) spectroscopy. Upon photolysis, two nearly but not completely overlapping sets of transient IR bands are observed that are assigned to two non-interconvertible conformers of mixed acetic nitronic anhydride 7. While syn-7 reverts rapidly to 1, anti-7 is

  [反应：见正文]使用纳秒时间分辨红外（TRIR）光谱技术在乙腈中研究了N-酰基-5,7-二硝基吲哚啉（1）的光化学。光解后，观察到两组几乎但不完全重叠的瞬态红外波段，它们被分配给混合的乙酸乙酸酐7的两个不可相互转化的构象。当syn-7迅速还原为1时，anti-7的寿命很长，并且是能够酰化胺。密度泛函理论计算的结果支持基于实验TRIR数据的结论。
• Biologically useful chelators that take up calcium(2+) upon illumination
  作者：S. R. Adams、J. P. Y. Kao、R. Y. Tsien

  DOI：10.1021/ja00202a042

  日期：1989.9
• Preparation of Photoactivable Amino Acid Derivatives
  作者：Jean-Luc Débieux、Christian G. Bochet

  DOI：10.1021/jo900442p

  日期：2009.6.19

  A range of N-protected-alpha-amino acyl-5,7-dinitroindolines 3a-z were prepared in good yields from commercially available N-protected-alpha-amino acids 1a-z by a two-step sequence of acylation and intramolecular amide N-arylation. Subsequent photochemical acylation of the N-protected-alpha-amino acyl-5,7-dinitroindolines 3e,g,r afforded the corresponding N-protected-alpha-amino acid amides 22e,g,r (77-92%) under mild conditions. All these reactions occurred with complete retention of chirality as evidenced by NMR analysis. This scheme provides an attractive and alternative method to the conventional acylation of alpha-amino acids, especially in cases where the amide bond needs to be formed without the use of a coupling reagent.