p-Nitrophenylcholine carbonate iodide

• 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: p-Nitrophenylcholine carbonate iodide
• 英文别名: p-nitrophenyl choline carbonate；p-nitrophenylcholine carbonate；para-nitrophenyl choline carbonate iodide；PNPCC；Trimethyl-[2-(4-nitrophenoxy)carbonyloxyethyl]azanium;iodide
• 化学式: C₁₂H₁₇N₂O₅*I
• 分子量: 396.182
• InChiKey: JUKBELPLRGONHN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.18
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-Nitrophenylcholine carbonate iodide 在 [1,2-(2-hydroxy-3,5-di-tert-butyl-CH=N-)benzene]-Zn cavitand 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 对硝基苯酚 、 碘化胆碱
  参考文献：
  名称：

  由一端密封而另一端功能化的合成受体催化

  摘要：

  带有锌 (II) 萨伦壁的深空腔催化对硝基苯胆碱碳酸盐的水解。空腔的封闭端适当地定位了基材的羰基官能团，以便被金属中心激活。乙酰胆碱衍生物的底物特异性来自同时的阳离子-pi 相互作用和 C=O- - -Zn 配位键。

  DOI：

  10.1021/ja045167x
• 作为产物：
  描述：

  对硝基苯基氯甲酸酯 以 乙腈 为溶剂， 生成 p-Nitrophenylcholine carbonate iodide
  参考文献：
  名称：

  Toward an Artificial Acetylcholinesterase

  摘要：

  The methanolysis of choline p-nitrophenylcarbonate in chloroform containing 1% methanal is catalyzed with turnover by ditopic receptors 1 and 2, consisting of a calix[6]arene connected to a bicyclic guanidinium by means of a short spacer. The calix[6]arene subunit strongly binds to the trimethylammonium head group through cation-ir interactions, whereas the guanidinium moiety is deputed to stabilize through hydrogen bonding reinforced by electrostatic attraction the anionic tetrahedral intermediate resulting from methoxide addition to the ester carbonyl, The observed cholinesterase activity had been anticipated on the basis of the ability of the ditopic receptors 1 and 2 to bind strongly to the choline phosphate DOPC, which is a transition state analogue far the B(Ac)2-type cleavage of choline esters.

  DOI：

  10.1002/1521-3765(20000901)6:17<3228::aid-chem3228>3.0.co;2-p

文献信息

• A Functionalized, Deep Cavitand Catalyzes the Aminolysis of a Choline Derivative
  作者：Arnaud Gissot、Julius Rebek

  DOI：10.1021/ja049074r

  日期：2004.6.23

  The aminolysis of choline p-nitrophenyl carbonate is catalyzed with turnover by a deep cavitand bearing an introverted pyridone function. The synergy of action between the recognition of the guest in the binding pocket and the catalytic activity brought to bear by the pyridone is responsible for the high substrate specificity observed.

  胆碱对硝基苯基碳酸酯的氨解由具有内向吡啶酮功能的深空腔催化转化。结合口袋中客体的识别与吡啶酮带来的催化活性之间的协同作用是观察到的高底物特异性的原因。
• Programmed Enzyme-Mimic Hydrolysis of a Choline Carbonate by a Metal-Free 2-Aminobenzimidazole-Based Cavitand
  作者：Bartolomé Soberats、Elena Sanna、Gabriel Martorell、Carmen Rotger、Antoni Costa

  DOI：10.1021/ol403612e

  日期：2014.2.7

  The hydrolysis of a choline carbonate through a metal-free, enzyme-like mechanism has been achieved using a 2-aminobenzimidazole-based deep cavitand as catalyst. The supramolecular catalysis involves three steps: host guest binding, carbamoylation and enzyme-like hydrolysis. Interestingly the rate-determining step proceeds through a programmed hydrolysis of carbamoylcholine-cavitand intermediate that may be driven by water molecules surrounding the benzimidazole walls of the cavity.