benzylcarbamic acid 1,1-dimethylprop-2-ynyl ester | 937021-08-4

• 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: benzylcarbamic acid 1,1-dimethylprop-2-ynyl ester
• 英文别名: 2-methylbut-3-yn-2-yl N-benzylcarbamate
• CAS: 937021-08-4
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: LCYNIKQRMWUCEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzylcarbamic acid 1,1-dimethylprop-2-ynyl ester 在 吡啶 、 copper(l) iodide 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 2-{4-[4-(benzylamino-diphenyl-methyl)-[1,2,3]triazol-1-yl]-butoxy}-benzoic acid 2-methoxy-ethyl 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
• 作为产物：
  描述：

  2-{4-[4-(benzylamino-diphenyl-methyl)-[1,2,3]triazol-1-yl]-butoxy}-benzoic acid 2-methoxy-ethyl ester 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 benzylcarbamic acid 1,1-dimethylprop-2-ynyl 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

• Au-Catalyzed [2 + 3] Annulation of Enamides with Propargyl Esters: Total Synthesis of Cephalotaxine and Cephalezomine H
  作者：Xiao-Yan Ma、Xian-Tao An、Xian-He Zhao、Ji-Yuan Du、Yu-Hua Deng、Xiang-Zhi Zhang、Chun-An Fan

  DOI：10.1021/acs.orglett.7b01202

  日期：2017.6.2

  A novel Au-catalyzed [2 + 3] annulation reaction of enamides with propargyl esters has been developed, providing a new method for expeditious assembly of synthetically useful functionalized 1-azaspiro[4.4]nonane building blocks. Based on this key annulation, strategic installation of the pivotal azaspirocyclic core, followed by constructing the benzazepine unit via Witkop cyclization, led to the divergent

  已经开发了一种新的Au催化的酰胺与炔丙基酯的[2 + 3]环化反应，为快速组装合成有用的功能化1-azaspiro [4.4]壬烷构件提供了新方法。基于这一关键的环空，战略性地安装了关键的氮杂螺环核心，然后通过Witkop环化构建苯并ze庚因单元，导致头孢他辛和头孢唑烷H的总合成有所不同。
• Click Chemistry with <i>O</i>-Dimethylpropargylcarbamate for Preparation of pH-Sensitive Functional Groups. A Case Study
  作者：Philippe Bertrand、Jean Pierre Gesson

  DOI：10.1021/jo070131j

  日期：2007.4.1

  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.