p-nitrophenyl 1-adamantanecarboxylate | 59711-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: p-nitrophenyl 1-adamantanecarboxylate
• 英文别名: 1-Adamantanecarboxylic acid, 4-nitrophenyl ester；(4-nitrophenyl) adamantane-1-carboxylate
• CAS: 59711-26-1
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: UMKLOSVMOXTTNX-UHFFFAOYSA-N

物化性质

• 沸点：
  439.0±28.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)
• 保留指数：
  2513

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  p-nitrophenyl 1-adamantanecarboxylate 在 β-环糊精 sodium hydroxide 、 乙腈 作用下， 反应 0.14h， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Catalysis of the Hydrolysis ofp-Nitrophenyl 1-Adamantaneacetate by Cyclodextrins

  摘要：

  β-和γ-环糊精加速了对硝基苯基 1-金刚烷乙酸酯的裂解，这与它们对立体类似底物--对硝基苯基 1-金刚烷羧酸酯--裂解的减速作用形成鲜明对比。这些底物中是否存在亚甲基完全决定了环糊精速率效应的方向。由于环糊精与这些底物的包合物结构不同，因此具有特异性，这明确表明环糊精是相当好的酶模型。

  DOI：

  10.1246/bcsj.53.3266
• 作为产物：
  描述：

  对硝基苯酚 、 1-金刚烷甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以90%的产率得到p-nitrophenyl 1-adamantanecarboxylate
  参考文献：
  名称：

  Square pegs in round holes. Preparation and intramolecular complexation of cubyl substituted β-cyclodextrins † and of an adamantane analogue

  摘要：

  1-甲氧羰基-4-(4-硝基苯氧羰基)立方烷或其二甲基类似物2,3-二甲基-1-甲氧羰基-4-(4-硝基苯氧羰基)立方烷与6A-(6-氨基己基)氨基-6A-脱氧-β-环糊精的一级胺反应，分别生成首例立方烷取代的β-环糊精：6A-脱氧-6A-{6-[N-(4-甲氧羰基立方烷-1-基羰基)氨基]己基氨基}-β-环糊精及其二甲基类似物和4-硝基苯酚。1,4-双(4-硝基苯氧羰基)立方烷与6A-(6-氨基己基)氨基-6A-脱氧-β-环糊精反应生成二聚体1,4-双{6-[N-(6A-脱氧-β-环糊精-6A-基)氨基]己基氨基羰基}立方烷。1H NMR ROESY研究表明，上述三种立方烷取代的β-环糊精中的立方烷部分在D2O中与β-环糊精环孔形成复合物。1-(4-硝基苯氧羰基)金刚烷与β-环糊精反应生成6A-{6-[N-(1-金刚烷基羰基)氨基]己基氨基}-6A-脱氧-β-环糊精，显示其金刚烷部分具有强烈的分子内复合作用。金刚烷-1-羧酸酯在D2O溶液中与上述三种立方烷取代的β-环糊精形成分子间复合物，并排斥立方烷部分进入β-环糊精环孔。然而，对于6A-{6-[N-(1-金刚烷基羰基)氨基]己基氨基}-6A-脱氧-β-环糊精，其分子内复合作用似乎足够强，足以防止金刚烷-1-羧酸酯的分子间复合作用。

  DOI：

  10.1039/a905390e

文献信息

• Photocatalytic Water‐Splitting Coupled with Alkanol Oxidation for Selective <i>N</i> ‐alkylation Reactions over Carbon Nitride
  作者：Yangsen Xu、Zhaofei Zhang、Chuntian Qiu、Shaoqin Chen、Xiang Ling、Chenliang Su

  DOI：10.1002/cssc.202002459

  日期：2021.1.21

  (PWST) enables the direct use of water as appealing “liquid hydrogen source” for transfer hydrogenation reactions. Currently, the development of PWST‐based transfer hydrogenations is still in an embryonic stage. Previous reports generally centered on the rational utilization of the in situ generated H‐source (electrons) for hydrogenations, in which photogenerated holes were quenched by sacrificial

  光催化水分解技术（PWST）可以将水直接用作转移加氢反应的吸引人的“液态氢源”。目前，基于PWST的转移氢化的开发仍处于萌芽阶段。以前的报道通常集中在合理利用原位生成的氢源（电子）进行氢化的过程中，其中通过牺牲试剂淬灭了光生空穴。本文介绍了光还原氮在水分解过程中对液体H源和孔的充分利用硝基芳族化合物的烷基化。在该集成系统中，将水分解过程中产生的H物种设计用于还原硝基芳烃以生成胺，而烷醇则被孔氧化以使苯胺以及生成的仲胺进行级联烷基化。在广泛范围内获得的50多个示例证明了这种温和且可持续的耦合方法的普遍适用性。通过胺的选择性N-烷基化合成现有药物，进一步证明了该方案的合成效用。这种基于可持续水分解技术的策略突出了选择性合成有价值的氮的重要途径。由硝基芳烃和胺与水和链烷醇一起烷基化的精细化学品和药物。
• Development of Potent and Selective Tissue Transglutaminase Inhibitors: Their Effect on TG2 Function and Application in Pathological Conditions
  作者：Eduard Badarau、Zhuo Wang、Dan L. Rathbone、Andrea Costanzi、Thomas Thibault、Colin E. Murdoch、Said El Alaoui、Milda Bartkeviciute、Martin Griffin

  DOI：10.1016/j.chembiol.2015.08.013

  日期：2015.10

  Potent-selective peptidomimetic inhibitors of tissue transglutaminase (TG2) were developed through a combination of protein-ligand docking and molecular dynamic techniques. Derivatives of these inhibitors were made with the aim of specific TG2 targeting to the intra-and extracellular space. A cell-permeable fluorescently labeled derivative enabled detection of in situ cellular TG2 activity in human umbilical cord endothelial cells and TG2-transduced NIH3T3 cells, which could be enhanced by treatment of cells with ionomycin. Reaction of TG2 with this fluorescent inhibitor in NIH3T3 cells resulted in loss of binding of TG2 to cell surface syndecan-4 and inhibition of translocation of the enzyme into the extracellular matrix, with a parallel reduction in fibronectin deposition. In human umbilical cord endothelial cells, this same fluorescent inhibitor also demonstrated a reduction in fibronectin deposition, cell motility, and cord formation in Matrigel. Use of the same inhibitor in a mouse model of hypertensive nephrosclerosis showed over a 40% reduction in collagen deposition.
• Lock; May; Clements, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 24, p. 3361 - 3364
  作者：Lock、May、Clements、Tsanaktsidis、Easton、Lincoln

  DOI：——

  日期：——
• Square pegs in round holes. Preparation and intramolecular complexation of cubyl substituted β-cyclodextrins † and of an adamantane analogue
  作者：Bruce L. May、Philip Clements、John Tsanaktsidis、Christopher J. Easton、Stephen F. Lincoln

  DOI：10.1039/a905390e

  日期：——

  The reaction of either 1-methoxycarbonyl-4-(4-nitrophenoxycarbonyl)cubane or its dimethyl analogue, 2,3-dimethyl-1-methoxycarbonyl-4-(4-nitrophenoxycarbonyl)cubane, with the primary amine of 6A-(6-aminohexyl)amino-6A-deoxy-β-cyclodextrin produces the first cubyl substituted β-cyclodextrins, 6A-deoxy-6A-6-[N-(4-methoxycarbonylcuban-1-ylcarbonyl)amino]hexylamino}-β-cyclodextrin and its dimethyl analogue, respectively, and 4-nitrophenolate. The reaction of 1,4-bis(4-nitrophenoxycarbonyl)cubane with 6A-(6-aminohexyl)amino-6A-deoxy-β-cyclodextrin produces the dimer 1,4-bis6-[N-(6A-deoxy-β-cyclodextrin-6A-yl)amino]hexylaminocarbonyl}cubane. 1H NMR ROESY studies are consistent with the cubyl moiety of each of the above three cubyl-substituted β-cyclodextrins complexing in the β-cyclodextrin annuli in D2O. The reaction of 1-(4-nitrophenoxycarbonyl)adamantane with β-cyclodextrin produces 6A-6-[N-(1-adamantylcarbonyl)amino]hexylamino}-6A-deoxy-β-cyclodextrin which shows a strong intramolecular complexation of its adamantyl moiety. Adamantane-1-carboxylate forms intermolecular complexes with the above three cubyl-substituted β-cyclodextrins in D2O solution and excludes the cubyl moiety from the β-cyclodextrin annulus. However, this does not occur for 6A-6-[N-(1-adamantylcarbonyl)amino]hexylamino}-6A-deoxy-β-cyclodextrin where intramolecular complexation appears to be sufficiently strong to prevent intermolecular complexation of adamantane-1-carboxylate.

  1-甲氧羰基-4-(4-硝基苯氧羰基)立方烷或其二甲基类似物2,3-二甲基-1-甲氧羰基-4-(4-硝基苯氧羰基)立方烷与6A-(6-氨基己基)氨基-6A-脱氧-β-环糊精的一级胺反应，分别生成首例立方烷取代的β-环糊精：6A-脱氧-6A-6-[N-(4-甲氧羰基立方烷-1-基羰基)氨基]己基氨基}-β-环糊精及其二甲基类似物和4-硝基苯酚。1,4-双(4-硝基苯氧羰基)立方烷与6A-(6-氨基己基)氨基-6A-脱氧-β-环糊精反应生成二聚体1,4-双6-[N-(6A-脱氧-β-环糊精-6A-基)氨基]己基氨基羰基}立方烷。1H NMR ROESY研究表明，上述三种立方烷取代的β-环糊精中的立方烷部分在D2O中与β-环糊精环孔形成复合物。1-(4-硝基苯氧羰基)金刚烷与β-环糊精反应生成6A-6-[N-(1-金刚烷基羰基)氨基]己基氨基}-6A-脱氧-β-环糊精，显示其金刚烷部分具有强烈的分子内复合作用。金刚烷-1-羧酸酯在D2O溶液中与上述三种立方烷取代的β-环糊精形成分子间复合物，并排斥立方烷部分进入β-环糊精环孔。然而，对于6A-6-[N-(1-金刚烷基羰基)氨基]己基氨基}-6A-脱氧-β-环糊精，其分子内复合作用似乎足够强，足以防止金刚烷-1-羧酸酯的分子间复合作用。
• Catalysis of the Hydrolysis of<i>p</i>-Nitrophenyl 1-Adamantaneacetate by Cyclodextrins
  作者：Makoto Komiyama、Shohei Inoue

  DOI：10.1246/bcsj.53.3266

  日期：1980.11

  The cleavage of p-nitrophenyl 1-adamantaneacetate was accelerated by β- and γ-cyclodextrins, which was in contrast with their deceleration of the cleavage of a sterically analogous substrate, p-nitrophenyl 1-adamantanecarboxylate. The presence and absence of a methylene group in these substrates absolutely governed the directions of the rate effects of the cyclodextrins. The specificity, explicitly showing that cyclodextrins are quite good models of enzymes, was attributed to the difference of the structures of the inclusion complexes of cyclodextrins with these substrates.

  β-和γ-环糊精加速了对硝基苯基 1-金刚烷乙酸酯的裂解，这与它们对立体类似底物--对硝基苯基 1-金刚烷羧酸酯--裂解的减速作用形成鲜明对比。这些底物中是否存在亚甲基完全决定了环糊精速率效应的方向。由于环糊精与这些底物的包合物结构不同，因此具有特异性，这明确表明环糊精是相当好的酶模型。