2-叠氮-1-苯并二氧戊环-5-乙酮 | 102831-07-2

• 物质功能分类: 化学试剂 - 有机试剂 - 叠氮
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 2-叠氮-1-苯并二氧戊环-5-乙酮
• 中文别名: 2-叠氮基-1-(1,3-苯并二氧代l-5-基)乙酮
• 英文名称: 2-azido-1-benzo[1,3]dioxol-5-ylethanone
• 英文别名: 3,4-(methylenedioxy)phenacyl azide；2-azido-1-(1,3-benzodioxol-5-yl)-1-ethanone；2-azido-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one；2-azido-1-(1,3-benzodioxol-5-yl)ethanone
• CAS: 102831-07-2
• 化学式: C₉H₇N₃O₃
• 分子量: 205.173
• InChiKey: NPLWBZVJJQJISJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-叠氮-1-苯并二氧戊环-5-乙酮 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 以81%的产率得到2-氨基-1-苯并[1,3]二氧代-5-乙酮盐酸盐
  参考文献：
  名称：

  Antimycobacterial natural products: synthesis and preliminary biological evaluation of the oxazole-containing alkaloid texaline

  摘要：

  Texaline, an antimycobacterial oxazole-containing alkaloid previously isolated from Amyris texana and A. elemifera, and related compounds have been synthesized in order to explore aspects of the structure-anti tuberculosis activity relationship. While texaline was found to be inactive in our assays, simpler diaryloxazoles were more active whilst also exhibiting modest toxic selectivity, leading to their identification as potential lead compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.119
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 生成 2-叠氮-1-苯并二氧戊环-5-乙酮
  参考文献：
  名称：

  Antimycobacterial natural products: synthesis and preliminary biological evaluation of the oxazole-containing alkaloid texaline

  摘要：

  Texaline, an antimycobacterial oxazole-containing alkaloid previously isolated from Amyris texana and A. elemifera, and related compounds have been synthesized in order to explore aspects of the structure-anti tuberculosis activity relationship. While texaline was found to be inactive in our assays, simpler diaryloxazoles were more active whilst also exhibiting modest toxic selectivity, leading to their identification as potential lead compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.119

文献信息

• Photolysis of α-Azidoacetophenones:  Direct Detection of Triplet Alkyl Nitrenes in Solution
  作者：Pradeep N. D. Singh、Sarah M. Mandel、Rachel M. Robinson、Zhendong Zhu、Roberto Franz、Bruce S. Ault、Anna D. Gudmundsdóttir

  DOI：10.1021/jo034674e

  日期：2003.10.1

  of triplet alkyl nitrenes in fluid solution by laser flash photolysis of alpha-azido acetophenone derivatives, 1. Alphazides 1 contain an intramolecular triplet sensitizer, which ensures formation of the triplet alkyl nitrene by bypassing the singlet nitrene intermediate. At room temperature, azides 1 cleave to form benzoyl and methyl azide radicals in competition with triplet energy transfer to form

  我们报告了通过α-叠氮基苯乙酮衍生物的激光闪光光解法对液体溶液中的三重态烷基氮的首次检测。1。叠氮化物1包含分子内三重态敏化剂，可通过绕过单重态氮烯中间体确保三重态烷基氮的形成。在室温下，叠氮化物1裂解形成苯甲酰基和叠氮化物自由基，与三重态能量转移竞争形成三重态烷基氮。主要的光产物3是由于三重烷基亚硝基被苯甲酰基所拦截而产生的。三线态烷基腈中间体也被分子氧捕获，得到相应的2-硝基苯基乙酮。1的激光闪光光解表明，三线态烷基腈具有约300 nm的吸收。通过在氩气基质中获得它们的UV和IR光谱，进一步表征了三线态烷基氮烯。（13）C和（15）N同位素标记研究使我们能够表征1201 cm（-）（1）处的丁腈中间体的CN延伸。
• Chemoproteomics-Enabled Discovery of a Potent and Selective Inhibitor of the DNA Repair Protein MGMT
  作者：Chao Wang、Daniel Abegg、Dominic G. Hoch、Alexander Adibekian

  DOI：10.1002/anie.201511301

  日期：2016.2.18

  covalent inhibitors. Chloromethyl triazoles (CMTs) are readily accessed in only two chemical steps, thus enabling the rapid optimization of the pharmacological properties of these inhibitors. We demonstrate the tunability of the CMTs towards a specific biological target by synthesizing AA‐CW236 as the first potent non‐pseudosubstrate inhibitor of the O6‐alkylguanine DNA methyltransferase (MGMT), a protein

  我们提出了一种用于半胱氨酸反应性共价抑制剂的新型化学支架。氯甲基三唑（CMT）只需两个化学步骤即可轻松获得，因此可以快速优化这些抑制剂的药理特性。通过合成AA-CW236作为O 6的第一种有效非伪底物抑制剂，我们证明了CMT向特定生物靶标的可调性-烷基鸟嘌呤DNA甲基转移酶（MGMT），一种对几种严重癌症形式的治疗具有重要临床意义的蛋白质。使用定量蛋白质组学分析技术，我们表明AA-CW236对MGMT表现出高度的选择性。最后，我们通过荧光成像和细胞活力分析验证了我们的MGMT抑制剂与DNA烷基化药物替莫唑胺在乳腺癌和结肠癌细胞中的有效性。我们的结果可能为临床批准的MGMT抑制剂的开发开辟新途径。
• [EN] CALCILYTIC COMPOUNDS<br/>[FR] COMPOSÉS CALCILYTIQUE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010039911A1

  公开（公告）日：2010-04-08

  Novel calcilytic compounds, pharmaceutical compositions, methods of synthesis and methods of using them are provided.

  提供了新型钙受体拮抗剂化合物、药物组合物、合成方法和使用方法。
• Visible-Light 2,4-Dinitrophenol-Mediated Photoannulation of α-Azidochalcones into 2,5-Diaryloxazoles
  作者：Uma Devi Newar、Satheesh Borra、Ram Awatar Maurya

  DOI：10.1021/acs.orglett.2c01691

  日期：2022.6.24

  photoannulation of α-azidochalcones into 2,5-diaryloxazoles was developed. The carbon–carbon double bond of α-azidochalcone was cleaved, leading to the formation of new C–O and C–N bonds in the photoannulation. Control experiments were carried out, and a plausible mechanism of the photoannulation was proposed. The scope of the reaction was studied by synthesizing a series of 2,5-diaryloxazoles including two

  开发了一种新型高效的可见光 2,4-二硝基苯酚 (2,4-DNP) 介导的 α-叠氮查尔酮光环化成 2,5-二芳基恶唑。α-叠氮查尔酮的碳碳双键被裂解，导致在光环化过程中形成新的 C-O 和 C-N 键。进行了对照实验，并提出了一种合理的光环化机制。通过以优异的收率合成一系列 2,5-二芳基恶唑，包括两种天然存在的恶唑（Texamine 和 Balsoxin），研究了反应的范围。
• DBU mediated coupling of isatin with phenacyl azides: synthesis of 2-oxoindolin-3-ylbenzoates
  作者：Uma Devi Newar、Kaushik Bora、Satheesh Borra、Ram Awatar Maurya

  DOI：10.1039/d2nj05661e

  日期：——

  Novel modes of reactivity of α-azido ketones towards isatin were discovered.

  发现了α-叠氮酮与靛红的新反应模式。