2-{4-[4-(1-hydroxy-1-methyl-ethyl)-[1,2,3]triazol-1-yl]-butoxy}-benzoic acid 2-methoxyethyl ester | 937021-10-8

• 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: 2-{4-[4-(1-hydroxy-1-methyl-ethyl)-[1,2,3]triazol-1-yl]-butoxy}-benzoic acid 2-methoxyethyl ester
• 英文别名: 2-Methoxyethyl 2-[4-[4-(2-hydroxypropan-2-yl)triazol-1-yl]butoxy]benzoate
• CAS: 937021-10-8
• 化学式: C₁₉H₂₇N₃O₅
• 分子量: 377.44
• InChiKey: ONDQLQOTZJHPOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-{4-[4-(1-hydroxy-1-methyl-ethyl)-[1,2,3]triazol-1-yl]-butoxy}-benzoic acid 2-methoxyethyl ester 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以45%的产率得到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：

  benzylcarbamic acid 1,1-dimethylprop-2-ynyl ester 在 吡啶 、 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 2-{4-[4-(1-hydroxy-1-methyl-ethyl)-[1,2,3]triazol-1-yl]-butoxy}-benzoic acid 2-methoxyethyl ester
  参考文献：
  名称：

  Novel triazolyl derivatives for acidic release of amines

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.11.026

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，
• Extending Triazolyl-Based Release under Mildly Acidic Conditions To Give Aniline Derivatives
  作者：Philippe Bertrand、Régis Delatouche、Christian Bachmann、Gilles Frapper

  DOI：10.1055/s-0031-1289719

  日期：2012.4

  Triazolyl derivatives of anilines were prepared and evaluated as releasing systems at mildly acidic pH values. Two triazolyl derivatives showed convenient pH sensitivity, being stable at pH 7.3 and rapidly hydrolyzed at pH values below 5. A generalized mechanism is proposed from additional theoretical investigations. hydrolysis - alkynes - azides - cycloaddition - amines - protonation

  制备苯胺的三唑基衍生物，并在弱酸性pH值下作为释放系统进行评估。两种三唑基衍生物显示了便利的pH敏感性，在pH 7.3时稳定，在pH值低于5时迅速水解。另外的理论研究提出了一种普遍的机理。 水解-炔烃-叠氮化物-环加成-胺-质子化