tert-butyl (4-nitrosobenzyl)carbamate

• 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 (4-nitrosobenzyl)carbamate
• 英文别名: tert-butyl N-[(4-nitrosophenyl)methyl]carbamate
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: DAGADKQFUOEEGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 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：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-nitrosobenzyl)carbamate 在 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.5h， 生成 (4-((1,3-dihydroisobenzofuran-5-yl)diazenyl)phenyl)methanamine
  参考文献：
  名称：

  Photoswitchable Pseudoirreversible Butyrylcholinesterase Inhibitors Allow Optical Control of Inhibition in Vitro and Enable Restoration of Cognition in an Alzheimer’s Disease Mouse Model upon Irradiation

  摘要：

  DOI：

  10.1021/jacs.1c13492
• 作为产物：
  描述：

  4-硝基苄胺 在 氯化铵 、 三乙胺 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 tert-butyl (4-nitrosobenzyl)carbamate
  参考文献：
  名称：

  Photoresponsive Supramolecular Architectures Based on Polypeptide Hybrids

  摘要：

  Self-aggregation has recently emerged as an efficient tool for the production of well-ordered supramolecular structures at the nanometric scale. In this framework, peptides offer important advantages as building blocks because of their biocompatibility and 3D-structural/functional diversities. The chemical diversity of peptides may be further expanded by use of noncoded amino acids. In the present work, we focused our attention on two known photoswitchable azobenzene-containing alpha-amino acids and used them as initiators for the reversible modulation of the cis/trans conformational states of two poly(gamma-benzyl-l-glutamate)-based hybrid molecules with either C-2 or C-3 symmetry. The microscopic photoresponsive self-assembly of these compounds was examined in detail. Moreover, these hybrids were exploited in the construction of macroscopic supramolecular architectures via the electrospinning technique. Finally, after appropriate thiol functionalization, we fabricated and characterized dimeric and trimeric gold nanoparticle/polypeptide hybrid systems.

  DOI：

  10.1021/ma501601r

文献信息

• Activation of Sirtuin 2 Inhibitors Employing Photoswitchable Geometry and Aqueous Solubility
  作者：Christoph W. Grathwol、Nathalie Wössner、Steven Behnisch‐Cornwell、Lukas Schulig、Lin Zhang、Oliver Einsle、Manfred Jung、Andreas Link

  DOI：10.1002/cmdc.202000148

  日期：2020.8.5

  derivatization with long‐chain fatty acids yielded potent sirtuin 2 inhibitors, featuring another intriguing aspect of azo‐based photoswitches. In these compounds, switching to the Z isomer increased aqueous solubility and thereby enhanced biological activity by up to a factor of 21. The biological activity of two compounds was confirmed by hyperacetylation of sirtuin specific histone proteins in a cell‐based activity

  由于在实验和治疗上极为相关的瑟土因家族的同工酶显示出高度的相似性，因此解决瑟土因2的独特选择性口袋是实现选择性抑制剂的一种有前途的策略。选择性抑制同工酶具有不同组织分布的不相关方法是靶向药物递送或通过光化学活化的时空活化。进行了两个烟酰胺模拟引线结构的偶氮化处理，以结合两种方法，得到了一组33种偶氮苯和偶氮吡啶，已对其光化学行为和生物活性进行了评估。对于某些化合物，抑制活性以其热力学上有利的E形式达到亚微摩尔范围，并且可以通过光异构化为亚稳态而降低Z形式。此外，用长链脂肪酸衍生化可产生有效的sirtuin 2抑制剂，这是基于偶氮的光开关的另一个有趣方面。在这些化合物中，改用Z异构体可增加水溶性，从而将生物活性提高至21倍。在基于细胞的活性测定中，沉默调节蛋白的特定组蛋白经过超乙酰化，从而证实了两种化合物的生物活性。
• Azobenzene-based chloride transporters with light-controllable activities
  作者：Ye Rin Choi、Gyu Chan Kim、Hae-Geun Jeon、Jinhong Park、Wan Namkung、Kyu-Sung Jeong

  DOI：10.1039/c4cc07560a

  日期：——

  Azobenzene-based chloride transporters exhibit photoresponsive transport activities across lipid and plasma membranes.

  基于偶氮苯的氯化物转运体在脂质和细胞膜上展现出光响应性的转运活性。
• Fluorescence photoswitching based on a photochromic pKa change in an aqueous solution
  作者：Tuyoshi Fukaminato、Emi Tateyama、Nobuyuki Tamaoki

  DOI：10.1039/c2cc35889a

  日期：——

  Reversible fluorescence photoswitching of RSA-AZO dyad 1 was clearly demonstrated in an acidic aqueous solution. The fluorescence photoswitching mechanism is based on the reversible ring opening/closing reactions of the RSA unit induced by a photochromic pK(a) change along with the photoisomerization of the AZO unit.

  RSA-AZO dyad 1的可逆荧光光开关在酸性水溶液中得到了明确证明。荧光光开关机制是基于由光致变色pK（a）的变化以及AZO单元的光异构化引起的RSA单元的可逆开/闭反应。
• Bridging the Binding Sites 2.0: Photoswitchable Dualsteric Ligands for the Cannabinoid 2 Receptor
  作者：Sophie A. M. Steinmüller、Anna Tutov、James N. Hislop、Michael Decker

  DOI：10.1021/acschemneuro.3c00509

  日期：2023.10.18

  The cannabinoid receptor 2 (CB2R) has high, unexploited therapeutic potential in several central nervous system disorders due to its involvement in neuroinflammatory processes and pathologies like neurodegeneration. Dualsteric/bitopic ligands are currently developed to achieve receptor subtype selectivity and biased signaling. To obtain a molecular tool compound with photoswitchable potential dualsteric

  大麻素受体 2 (CB 2 R) 由于参与神经炎症过程和神经变性等病理，因此在多种中枢神经系统疾病中具有尚未开发的高治疗潜力。目前开发了双立体/双位配体以实现受体亚型选择性和偏向信号传导。为了获得具有光可切换潜在双立体特性的分子工具化合物，我们应用了两种不同的方法通过光致变色单元将正变构调节剂与正位激动剂连接起来。我们表征了所有化合物的光物理性质，并确定了内化、钙动员和 BRET 研究的功效。我们报告了第一个潜在的双立体光开关配体，用于研究 CB 2 R 相关病理的分子机制。化合物17 - para是一种亚微摩尔“顺式”激动剂，与其反式光异构体相比，其效力高出 10 倍以上，并且可以高度时空控制 CB 2 R 激活。
• Efficient Preparation of Nitrosoarenes for the Synthesis of Azobenzenes
  作者：Beate Priewisch、Karola Rück-Braun

  DOI：10.1021/jo048544x

  日期：2005.3.1

  Reaction conditions are described for the oxidation of anilines furnishing nitrosoarenes and the synthesis of unsymmetrically substituted azobenzenes. In a comparative study, the catalytic oxidation of methyl 4-aminobenzoate by hydrogen peroxide was investigated, and SeO2 proved to be superior or equal to methyl trioxorhenium (MTO) and Na2WO4, respectively. Nevertheless, the application of the inexpensive, environmentally friendly, Oxone in a biphasic system proved to be more efficient, and a variety of useful nitrosoarenes for the synthesis of azo compounds were prepared in high yield and purity on a large scale.