carbonic acid 1,1-dimethylprop-2-ynyl 4-nitrophenyl ester | 154044-78-7

• 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: carbonic acid 1,1-dimethylprop-2-ynyl 4-nitrophenyl ester
• 英文别名: 1,1-dimethylprop-2-ynyl (4-nitrophenyl)carbonate；4-nitrophenol dimethylpropargyloxycarbonate；2-Methylbut-3-yn-2-yl (4-nitrophenyl) carbonate
• CAS: 154044-78-7
• 化学式: C₁₂H₁₁NO₅
• 分子量: 249.223
• InChiKey: ODYCFJJATMTYFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  carbonic acid 1,1-dimethylprop-2-ynyl 4-nitrophenyl ester 在 盐酸 、 L-ascorbic acid sodium salt 、 potassium chloride 、 对甲苯磺酸 、 copper(II) sulfate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 、 苯 为溶剂， 反应 7.5h， 生成 2-[4-(4-isoprenyl-[1,2,3]triazol-1-yl)-butoxy]-benzoic acid 2-methoxyethyl ester
  参考文献：
  名称：

  Click Chemistry with O-Dimethylpropargylcarbamate for Preparation of pH-Sensitive Functional Groups. A Case Study

  摘要：

  Click chemistry has became an important tool for molecular constructs such as biopolymers. During the development of biodegradable multifunctional poly(ethylene oxide) (PEO) polymers suitable for click chemistry in water, an unexpected reaction leading to a mixture of triazole cycloadducts was observed. This result was attributed to an intramolecular ligand effect, and alternative conditions were evaluated. An efficient method was then implemented allowing the access in high yields to the expected triazolylcarbamate. pH sensitivity of the obtained isopropyltriazolylcarbamate was demonstrated at acidic pH.

  DOI：

  10.1021/jo070131j
• 作为产物：
  描述：

  对硝基苯基氯甲酸酯 、 2-甲基-3-丁炔-2-醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 carbonic acid 1,1-dimethylprop-2-ynyl 4-nitrophenyl ester
  参考文献：
  名称：

  用于可逆蛋白质和细胞表面修饰的铜触发生物正交切割反应

  摘要：

  对蛋白质和细胞偶联物的时间和可逆控制具有在肿瘤部位无痕释放抗体药物偶联物 (ADC) 以及按需改变或去除细胞表面上的靶向元件的巨大潜力。我们在此开发了一种对蛋白质和完整细胞的生物正交和无痕可释放反应来实现这些目的。对催化生物正交裂解反应的过渡金属的系统调查表明，铜配合物如 Cu(I)-BTTAA 和双取代炔丙基 (dsPra) 或炔丙基氧羰基 (dsProc) 部分提供了生物正交可释放对，用于可逆的阻塞和拯救小分子药物、蛋白质侧链以及完整细胞表面上的伯胺和酚醇。对于概念验证，我们采用这种 Cu(I)-BTTAA/dsProc 和 Cu(I)-BTTAA/dsPra 对作为“无痕链接器”策略来构建可切割的 ADC 以在癌细胞上原位释放细胞毒性化合物，并作为“可逆修饰”策略用于细胞表面工程。此外，通过与基因编码扩展策略相结合，我们在活细胞膜上对配体-受体相互作用进行了位点特异性调节。总之，我们

  DOI：

  10.1021/jacs.9b05833

文献信息

• Triazolyl Derivatives for Acidic Release of Alcohols
  作者：Martine Mondon、Régis Delatouche、Christian Bachmann、Gilles Frapper、Christophe Len、Philippe Bertrand

  DOI：10.1002/ejoc.201001677

  日期：2011.4

  obtained. The rate of hydrolysis of these ethers ramged from a few hours to several days. A theoretical investigation demonstrated that the acidic release of alcohols from triazole derivatives proceeds first by protonation of the triazole ring followed by proton transfer from the triazole ring to the carbonyl group of the carbonates or to the oxygen atom of the ether derivatives. The rate of the decomposition

  新的基于三唑基的碳酸酯和醚已被研究作为弱酸性条件下潜在的醇释放系统。三唑基碳酸酯由于其明显的不稳定性而无法制备，而成功地获得了醚。这些醚的水解速度从几小时到几天不等。一项理论研究表明，醇从三唑衍生物的酸性释放首先通过三唑环的质子化进行，然后质子从三唑环转移到碳酸酯的羰基或醚衍生物的氧原子。分解反应的速率取决于中间 C-NH+/E-NH+ 结构中 N3–H...O 氢键的长度和三唑碳正离子的稳定性，
• [EN] O-ALKYL TRIAZOLYL CARBAMATES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE (FAAH)<br/>[FR] CARBAMATES DE O-ALKYLTRIAZOLYLE EN TANT QU'INHIBITEURS DE L'HYDROLASE DES AMIDES D'ACIDES GRAS (FAAH)
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2015007613A1

  公开（公告）日：2015-01-22

  The present invention provides compounds of formula I and pharmaceutical compositions for inhibiting fatty acid amide hydrolase (FAAH). Inhibition of FAAH is contemplated as a method to sustain the levels of the fatty acid ethanolamides arachidonoylethanolamide (AEA), palmitoylethanolamide (PEA), and oleoylethanolamide (OEA), three substrates of FAAH, in conditions characterized byreduced concentrations of AEA, PEA and OEA. The invention also provides methods for treating disorders in which decreased levels of AEA, PEA and OEA are associated with the disorder.

  本发明提供了式I的化合物和用于抑制脂肪酸酰胺水解酶（FAAH）的药物组合物。考虑到通过抑制FAAH来维持脂肪酸乙醇胺花生四烯酰胺（AEA）、棕榈酰胺乙醇胺（PEA）和油酰胺乙醇胺（OEA）这三种FAAH底物的水平的方法，适用于在其特征为AEA、PEA和OEA浓度降低的情况下。本发明还提供了治疗与降低的AEA、PEA和OEA水平相关的疾病的方法。
• Stable Alkynyl Glycosyl Carbonates: Catalytic Anomeric Activation and Synthesis of a Tridecasaccharide Reminiscent of<i>Mycobacterium tuberculosis</i>Cell Wall Lipoarabinomannan
  作者：Bijoyananda Mishra、Mahesh Neralkar、Srinivas Hotha

  DOI：10.1002/anie.201511695

  日期：2016.6.27

  a challenging task despite the advent of modern glycosidation techniques. Herein, alkynyl glycosyl carbonates are shown to be stable glycosyl donors that can be activated catalytically by gold and silver salts at 25 °C in just 15 min to produce glycosides in excellent yields. Benzoyl glycosyl carbonate donors are solid compounds with a long shelf life. This operationally simple protocol was found to

  尽管现代糖苷化技术的出现，寡糖的合成仍然是一项艰巨的任务。本文中，炔基糖基碳酸酯显示为稳定的糖基供体，其可在25℃下仅15分钟内被金和银盐催化活化，从而以优异的产率产生糖苷。苯甲酰基糖基碳酸酯供体是具有长保存期限的固体化合物。发现该操作简单的方案对于核苷，氨基酸以及酚和叠氮基糖缀合物的合成是高效的。碳酸盐糖苷化方法的重复使用使得十三碳阿拉伯甘露聚糖能够以快速的方式高度收敛地合成。
• Novel triazolyl derivatives for acidic release of amines
  作者：Regis Delatouche、Martine Mondon、Adrià Gil、Gilles Frapper、Christian Bachmann、Philippe Bertrand

  DOI：10.1016/j.tet.2010.11.026

  日期：2011.1

  Triazolyl derivatives of amines were prepared using click chemistry and evaluated as releasing systems in mildly acidic environments. Triazolylcarbamates and alkylamines were obtained, depending on the reactivity of the propargylic intermediates used for the Huisgen cycloaddition. A fast hydrolysis of some derivatives in mildly acidic conditions was achieved. The relative rates were correlated to a proposed mechanism highlighting the complementary role of the triazole ring and carbocation reactivity/stability. (C) 2010 Elsevier Ltd. All rights reserved.
• Development of Biocompatible Cu(I)‐Microdevices for Bioorthogonal Uncaging and Click Reactions
  作者：Melissa van de L'Isle、Stephen Croke、Teresa Valero、Asier Unciti‐Broceta

  DOI：10.1002/chem.202400611

  日期：2024.5.28

  Transition‐metal‐catalyzed bioorthogonal reactions emerged a decade ago as a novel strategy to implement spatiotemporal control over enzymatic functions and pharmacological interventions. The use of this methodology in experimental therapy is driven by the ambition of improving the tolerability and PK properties of clinically‐used therapeutic agents. The preclinical potential of bioorthogonal catalysis has been validated in vitro and in vivo with the in situ generation of a broad range of drugs, including cytotoxic agents, anti‐inflammatory drugs and anxiolytics. In this article, we report our investigations towards the preparation of solid‐supported Cu(I)‐microdevices and their application in bioorthogonal uncaging and click reactions. A range of ligand‐functionalized polymeric devices and off‐on Cu(I)‐sensitive sensors were developed and tested under conditions compatible with life. Last, we present a preliminary exploration of their use for the synthesis of PROTACs through CuAAC assembly of two heterofunctional mating units.