tert-butyl 2-bromo-2-(2-nitrophenyl)acetate | 158078-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 2-bromo-2-(2-nitrophenyl)acetate
• CAS: 158078-62-7
• 化学式: C₁₂H₁₄BrNO₄
• 分子量: 316.151
• InChiKey: JUXJMAGTVHTGCK-UHFFFAOYSA-N

物化性质

• 沸点：
  380.9±27.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-bromo-2-(2-nitrophenyl)acetate 在 4-二甲氨基吡啶 、 silver perchlorate 、 N,N'-二环己基碳二亚胺 、 丙酮 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 100.0h， 生成
  参考文献：
  名称：

  PHOTOLABILE ‘CAGED’ FATTY ACIDS CONTAINING A 1-(2′-NITROPHENYL)-1,2-ETHANEDIOL MOIETY

  摘要：

  DOI：

  10.1016/s0960-894x(97)00199-6
• 作为产物：
  描述：

  2-(2-硝基苯基)乙酰氯 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 tert-butyl 2-bromo-2-(2-nitrophenyl)acetate
  参考文献：
  名称：

  Synthesis and Photochemistry of a New Photolabile Derivative of GABA-Neurotransmitter Release and Receptor Activation in the Microsecond Time Region

  摘要：

  DOI：

  10.1021/ja00097a054

文献信息

• DOUBLE CAGED GABA COMPOUNDS, BIS-CNB-GABA
  申请人：The Trustees of Princeton University

  公开号：US20150266809A1

  公开（公告）日：2015-09-24

  Double caged GABA compounds and compositions including the same are described. Methods of synthesizing and using double caged GABA compounds are provided.

  描述了双笼式GABA化合物及包括其在内的组合物。提供了合成和使用双笼式GABA化合物的方法。
• Competition between cleavage and decarboxylation in photolysis of α-carboxy-2-nitrobenzyl protected cysteine derivatives
  作者：Nico Kotzur、Benoît Briand、Michael Beyermann、Volker Hagen

  DOI：10.1039/b900865a

  日期：——

  Photolysis of model peptides containing α-carboxy-2-nitrobenzyl (CNB) or α-carboxy-4,5-dimethoxy-2-nitrobenzyl (CDMNB) protected cysteines in aqueous solution gives the expected 2-nitrobenzyl-type photocleavage and can be accompanied by photodecarboxylation depending on structural aspects.

  水溶液中含α-羧基-2-硝基苄基（CNB）或α-羧基-4,5-二甲氧基-2-硝基苄基（CDMNB）保护的半胱氨酸模型的光分解，给出了预期的2-硝基苄基型光裂解，并可伴随结构方面的光脱羧反应。
• Synthesis and Biological Evaluation of Bis-CNB-GABA, a Photoactivatable Neurotransmitter with Low Receptor Interference and Chemical Two-Photon Uncaging Properties
  作者：Diana D. Shi、Federico F. Trigo、Martin F. Semmelhack、Samuel S.-H. Wang

  DOI：10.1021/ja411082f

  日期：2014.2.5

  Photoactivatable "caged" neurotransmitters allow optical control of neural tissue with high spatial and temporal precision. However, the development of caged versions of the chief vertebrate inhibitory neurotransmitter, gamma-amino butyric acid (GABA), has been limited by the propensity of caged GABAs to interact with GABA receptors. We describe herein the synthesis and application of a practically useful doubly caged GABA analog, termed bis-alpha-carboxy-2-nitrobenzyl-GABA (bis-CNB-GABA). Uncaging of bis-CNB-GABA evokes inward GABAergic currents in cerebellar molecular layer interneurons with rise times of 2 ms, comparable to flash duration. Response amplitudes depend on the square of flash intensity, as expected for a chemical two-photon uncaging effect. Importantly, prior to uncaging, bis-CNB-GABA is inactive at the GABA(A) receptor, evoking no changes in holding current in voltage-clamped neurons and showing an IC50 of at least 2.5 mM as measured using spontaneous GABAergic synaptic currents. Bis-CNB-GABA is stable in solution, with an estimated half-life of 98 days in the light. We expect that bis-CNB-GABA will prove to be an effective tool for high-resolution chemical control of brain circuits.
• Caged Bioactive Carboxylates. Synthesis, Photolysis Studies, and Biological Characterization of a New Caged N-Methyl-D-aspartic Acid
  作者：Kyle R. Gee、Li Niu、Klaus Schaper、George P. Hess

  DOI：10.1021/jo00118a050

  日期：1995.6
• US5635608A
  申请人：——

  公开号：US5635608A

  公开（公告）日：1997-06-03