4-nitrophenyl prop-2-yn-1-yl carbonate | 228111-40-8

• 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: 4-nitrophenyl prop-2-yn-1-yl carbonate
• 英文别名: (4-nitrophenyl) prop-2-ynyl carbonate
• CAS: 228111-40-8
• 化学式: C₁₀H₇NO₅
• 分子量: 221.169
• InChiKey: ZFSTXYJGQDNJRW-UHFFFAOYSA-N

物化性质

• 沸点：
  354.2±42.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  4-nitrophenyl prop-2-yn-1-yl carbonate 、 propyl L-alaninate hydrochloride 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 propyl ((prop-2-yn-1-yloxy)carbonyl)-L-alaninate
  参考文献：
  名称：

  Synthesis and Secondary Structure of Poly(1-methylpropargyl-N-alkylcarbamate)s

  摘要：

  A series of novel 1-methylpropargyl-N-alkylcarbamates, HC C-(R)-CH(CH3)OCONHCH2-CO2CH2CH2](R)-1HC C-(S)-CH(CH3)OCONHCH2CO2CH2CH2[(S)-1], HC C-(S)-CH(CH3)-OCONH-(R)-CH(CH3)CH2CH2CH2CH2CH2CH3[(s),(R)'-2], HC C-(S)-CH(CH3)OCONH-(R)-CH(CH3)CO2-CH2CH2CH3[(S),(R)-3], HC CCH2OCONH-(R)-CH(CH3)CO2CH2CH2CH3 [(R)'-4, HC CCH2OCONH-(S)-CH(CH3)CO2CH2CH2CH3[(S)'-4], and HC CCH2OCONHCH2CO2CH2CH2CH3 (5) were synthesized and r olymel Ind using (nbd)Rh+[eta(6)-C6H5B-(C6H5)(3)] (nbd = bornachene) as a catalyst Substituted cis-stereoregular polyacetylencs with moderate molecular weights were obtained in good yields Polyl(R)-1.1, polyl(S)- I, polyl(S),(RY-2), and poly[(5),(R)1-31 exhibited laige optical rotations (vertical bar[alpha](D)vertical bar= 344 degrees -508 degrees), clear CD signal; (Ar = 4 8-7 0 M-1 cm-1) in CliC11, and Inch viscosity indices (0 82-0 87), demonstrating the formation or-helical structures with predominantly one-handed sciew sense, which wei c stable up to 55 degrees C in the solvent The solution state IR measurement confirmed the presence of mtramolecular hydrogen bonding between the pendent carbamate groups of the polymers Chiral amplification was observed in chiral/achiral [(S)-1/5] and R/S [(R)-I /(S)-1] copolymei izations Conformational analysis revealed that the polymers adopt a tightly twisted helical conformation with a dihedral angle of 70 degrees at the single bond on the main chain The molecular mechanics calcul.ition and X-ray diffraction measurement suggested that the diameter of the helix is 25 and 17 angstrom, respectively.

  DOI：

  10.1021/ma100937k
• 作为产物：
  描述：

  2-丙炔-1-醇 、 对硝基苯基氯甲酸酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到4-nitrophenyl prop-2-yn-1-yl carbonate
  参考文献：
  名称：

  生命系统中金触发的释放化学。

  摘要：

  生物正交催化的最新进展正在提高研究人员操纵复杂生物系统中分子命运的能力。提出了一种生物正交解笼锁策略，该策略由异质金催化触发，并促进癌细胞培养物中结构多样的治疗药物的激活。此外，这种固体支撑的催化系统首次实现了荧光染料局部受控释放到斑马鱼大脑中，为调节最脆弱和最复杂器官中生物正交试剂的活性提供了一种新方法。

  DOI：

  10.1002/anie.201705609

文献信息

• A “Catch-and-Release” Protocol for Alkyne-Tagged Molecules Based on a Resin-Bound Cobalt Complex for Peptide Enrichment in Aqueous Media
  作者：Ayako Miyazaki、Miwako Asanuma、Kosuke Dodo、Hiromichi Egami、Mikiko Sodeoka

  DOI：10.1002/chem.201400056

  日期：2014.6.23

  and mild protocols for the specific enrichment of biomolecules is of significant interest from the perspective of chemical biology. A cobalt–phosphine complex immobilised on a solid‐phase resin has been found to selectively bind to a propargyl carbamate tag, that is, “catch”, under dilute aqueous conditions (pH 7) at 4 °C. Upon acidic treatment of the resulting resin‐bound alkyne–cobalt complex, the Nicholas

  从化学生物学的观点出发，对于生物分子的特异性富集的新的和温和的方案的开发引起了极大的兴趣。已发现固定在固相树脂上的钴膦复合物在4°C的稀水条件（pH 7）下选择性地结合到炔丙基氨基甲酸酯标签上，即“捕获”。在对所得的与树脂结合的炔-钴络合物进行酸性处理后，引发了尼古拉斯反应，以游离胺的形式从树脂中“释放”了炔标记的分子。模型研究表明，可以在4°C的条件下实现对炔烃标记分子的选择性富集。概念验证适用于带有炔烃标记的氨基酸和二肽。使用炔烃标记的二肽进行的研究证明，该方案与在侧链中具有一系列功能的各种氨基酸兼容。此外，在各种肽存在下，选择性富集和检测衍生自炔烃标记的二肽的“捕获和释放”的胺已在高度稀释的条件下完成（如质谱法所测定）。
• [EN] POLYMERIC CONJUGATES AND USES THEREOF<br/>[FR] CONJUGUÉS POLYMÈRES ET LEURS UTILISATIONS
  申请人：FUNDACION DE LA COMUNIDAD VALENCIANA CENTRO DE INVESTIG PRINCIPE FELIPE

  公开号：WO2020193802A1

  公开（公告）日：2020-10-01

  The present invention relates to novel chemical entities comprising a polymeric carrier incorporating covalently linked drug(s) as well as their pharmaceutical compositions containing the said polymer-drug conjugates as pharmaceutical agents and their uses thereof in therapy and, more particularly, but not exclusively, to novel conjugates having attached thereto a targeting moiety, an imaging agent and one or more therapeutic agents to promote axonal growth and for the treatment of neurodegenerative and inflammatory diseases, central nervous system traumatic injuries and cancer.

  本发明涉及一种新型化学实体，包括将药物共价连接到聚合载体中的药物，以及包含所述聚合物-药物共轭物作为药物代理的药物组合物，以及它们在治疗中的用途，更具体地说，但不限于，涉及附有靶向基团、成像剂和一个或多个治疗剂的新型共轭物，用于促进轴突生长和治疗神经退行性和炎症性疾病、中枢神经系统创伤性损伤和癌症。
• Catch and release of alkyne-tagged molecules in water by a polymer-supported cobalt complex
  作者：Hiromichi Egami、Shinji Kamisuki、Kosuke Dodo、Miwako Asanuma、Yoshitaka Hamashima、Mikiko Sodeoka

  DOI：10.1039/c1ob06123b

  日期：——

  A cobalt–phosphine complex supported on PS-PEG beads was found to react with a propargyl carbamate tag, and the tagged molecules immobilized on the beads could be released by acidic treatment through the Nicholas reaction pathway. These reactions work in aqueous media at 4 °C, so that this catch and release procedure is compatible with conditions generally used in biochemical experiments.

  一种以PS-PEG微珠为支撑的钴-膦复合物被发现能够与丙炔基氨基甲酸酯标签反应，固定在微珠上的标记分子可以通过酸性处理通过尼古拉斯反应途径释放。这些反应在4℃的水性介质中进行，因此这一捕获与释放的过程与生化实验中通常使用的条件兼容。
• 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。
• [EN] AMATOXIN DERIVATIVES AND CONJUGATES THEREOF AS INHIBITORS OF RNA POLYMERASE<br/>[FR] DÉRIVÉS D'AMATOXINE ET LEURS CONJUGUÉS À UTILISER EN TANT QU'INHIBITEURS DE L'ARN POLYMÉRASE
  申请人：NOVARTIS AG

  公开号：WO2017191579A1

  公开（公告）日：2017-11-09

  The invention disclosed herein relates to cytotoxic cyclic peptides of Formula (A), methods of inhibiting RNA polymerase with such cyclic peptides, immunoconjugates comprising such cyclic peptides (i.e Antibody Drug Conjugates), pharmaceutical compositions comprising such cyclic peptides immunoconjugates, compositions comprising such cyclic peptides immunoconjugates with a therapeutic co-agent and methods of treatment using such cyclic peptides immunoconjugates.

  本发明涉及公式（A）的细胞毒性环肽，以及利用这些环肽抑制RNA聚合酶的方法，包括这些环肽的免疫结合物（即抗体药物结合物），包含这些环肽免疫结合物的药物组合物，含有这些环肽免疫结合物和治疗性辅助剂的组合物，以及利用这些环肽免疫结合物进行治疗的方法。