5-bromo-7-nitroindoline-1-carbonyl chloride | 959794-48-0

• 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
• 英文名称: 5-bromo-7-nitroindoline-1-carbonyl chloride
• 英文别名: 5-Bromo-7-nitro-2,3-dihydroindole-1-carbonyl chloride；5-bromo-7-nitro-2,3-dihydroindole-1-carbonyl chloride
• CAS: 959794-48-0
• 化学式: C₉H₆BrClN₂O₃
• 分子量: 305.515
• InChiKey: HRAMDJVYQADQBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-7-nitroindoline-1-carbonyl chloride 、 4-叔丁基苯胺 在 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到
  参考文献：
  名称：

  胺和醇的光敏保护基团：N-取代的 7-硝基二氢吲哚的光解

  摘要：

  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。

  DOI：

  10.1055/s-2007-985580
• 作为产物：
  描述：

  5-溴-7-硝基二氢吲哚 、 三光气 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到5-bromo-7-nitroindoline-1-carbonyl chloride
  参考文献：
  名称：

  胺和醇的光敏保护基团：N-取代的 7-硝基二氢吲哚的光解

  摘要：

  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。

  DOI：

  10.1055/s-2007-985580

文献信息

• Wavelength-Selective Caged Surfaces: How Many Functional Levels Are Possible?
  作者：Verónica San Miguel、Christian G. Bochet、Aránzazu del Campo

  DOI：10.1021/ja110572j

  日期：2011.4.13

  The possibility of wavelength-selective cleavage of seven photolabile caging groups from different families has been studied. Amine-, thiol-, and carboxylic-terminated organosilanes were caged with o-nitrobenzyl (NVOC, NPPOC), benzoin (BNZ), (coumarin-4-yl)methyl (DEACM), 7-nitroindoline (DNI, BNI), and p-hydroxyphenacyl (pHP) derivatives. Caged surfaces modified with the different chromophores were prepared, and their photosensitivity at selected wavelengths was quantified. Different pairs, trios, and quartets of chromophore combinations with wavelength-selective photoresponse were identified. Our results show, for the first time, the possibility of generating surfaces with up to four different and independently addressable functional levels. In addition, this manuscript presents the first systematic comparison of the photolytic properties of different photolabile groups under different irradiation conditions.
• Photocleavable Protecting Groups
  申请人：Barone Anthony D.

  公开号：US20100324266A1

  公开（公告）日：2010-12-23

  Novel compounds are provided, which are useful as linking groups in chemical synthesis, preferably in the solid phase synthesis of oligonucleotides and polypeptides. These compounds are generally photolabile and comprise protecting groups which can be removed by photolysis to unmask a reactive group. The protecting group has the general formula Y, wherein Y is a chemical structure as shown in FIG. 1 . Also provided is a method of forming, from component molecules, a plurality of compounds on a support, each compound occupying a separate predefined region of the support, using the protected compounds described above.
• 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。