甲基3-烯丙基-4-氨基苯甲酸酯 | 267002-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基3-烯丙基-4-氨基苯甲酸酯
• 英文名称: 3-allyl-4-aminobenzoate
• 英文别名: 3-Allyl-4-amino-benzoic acid methyl ester；Methyl 3-allyl-4-aminobenzoate；methyl 4-amino-3-prop-2-enylbenzoate
• CAS: 267002-59-5
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: XHLKKYLFVXNAER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基3-烯丙基-4-氨基苯甲酸酯 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 37.0h， 生成 methyl 6-oxo-6,13-dihydro-5H-dibenzo[b,g]azonine-2-carboxylate
  参考文献：
  名称：

  Synthesis of nitrogen-containing benzoannulated eight- and nine-membered heterocycles from methyl 4-amino-3-iodobenzoate

  摘要：

  Dibenzo[b,f]azocin-6(5H)-one and dibenzo[b,g]azonin-6(13H)-one were prepared in five steps from methyl 4-amino-3-iodobenzoate.

  DOI：

  10.1016/j.mencom.2014.04.011
• 作为产物：
  描述：

  4-氨基苯甲酸甲酯 在 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 14.0h， 生成 甲基3-烯丙基-4-氨基苯甲酸酯
  参考文献：
  名称：

  Novel strategies for the solid phase synthesis of substituted indolines and indoles

  摘要：

  Using a polymer-bound selenenyl bromide resin, o-allyl and o-prenyl anilines were cycloaded to afford a series of solid-supported indoline and indole scaffolds. These scaffolds were then functionalized and cleaved via four distinct methods, namely traceless reduction, radical cyclization, radical rearrangement, and oxidative elimination, to afford 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines, respectively. A number of small combinatorial libraries of compounds reminiscent of certain designed ligands of biological interest were constructed demonstrating the potential utility of the developed methodology to chemical biology studies and the drug discovery process. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00386-3

文献信息

• Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate
  作者：Jiaming Li、Robert H. Grubbs、Brian M. Stoltz

  DOI：10.1021/acs.orglett.6b02722

  日期：2016.11.4

  A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.

  以分子氧为氧化剂，实现了一种温和需氧分子内氨基乙酰氧基化合成吡咯烷和二氢吲哚衍生物的方法。催化NO x物质充当电子转移介体，以获取高价钯中间体作为假定的活性氧化剂。
• Palladium(II)-Catalyzed Oxidative Cascade Cyclization Reactions of Anilides and Anilines: Scope and Mechanistic Investigations
  作者：Kai-Tai Yip、Dan Yang

  DOI：10.1002/asia.201100242

  日期：2011.8.1

  catalyst system and molecular oxygen as a green oxidant, acrylanilides and N‐allylanilines undergo oxidative cascade cyclization to form heterocyclic rings in high yields. This methodology is applicable to acrylanilides of different substitution patterns on olefinic units. Mechanistic studies revealed that cyclization of acrylanilides proceeded through an intramolecular syn‐amidopalladation pathway. The

  以Pd（OAc）2 /吡啶为催化剂体系，以分子氧为绿色氧化剂，丙烯酰苯胺和N-烯丙基苯胺经过氧化级联环化反应以高产率形成杂环。该方法学适用于烯烃单元上不同取代方式的丙烯酰苯胺。机理研究表明，丙烯酰胺的环化过程是通过分子内合成来进行的。-泛乳化途径。酰胺基palladation的可逆性质是一个“清除过程”，以防止在催化循环中途发生β-氢化物消除，从而有利于级联环化产物的形成。另外，σ-烷基钯物质与链状烯烃CC双键之间的内部配位似乎也不利于β-氢化物的消除。
• A Novel Strategy for the Solid-Phase Synthesis of Substituted Indolines
  作者：K. C. Nicolaou、A. J. Roecker、Jeffrey A. Pfefferkorn、Gou-Qiang Cao

  DOI：10.1021/ja994373f

  日期：2000.3.1
• Novel strategies for the solid phase synthesis of substituted indolines and indoles
  作者：K Nicolaou

  DOI：10.1016/s0968-0896(02)00386-3

  日期：2003.2.6

  Using a polymer-bound selenenyl bromide resin, o-allyl and o-prenyl anilines were cycloaded to afford a series of solid-supported indoline and indole scaffolds. These scaffolds were then functionalized and cleaved via four distinct methods, namely traceless reduction, radical cyclization, radical rearrangement, and oxidative elimination, to afford 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines, respectively. A number of small combinatorial libraries of compounds reminiscent of certain designed ligands of biological interest were constructed demonstrating the potential utility of the developed methodology to chemical biology studies and the drug discovery process. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of nitrogen-containing benzoannulated eight- and nine-membered heterocycles from methyl 4-amino-3-iodobenzoate
  作者：Mohammad Hassam、Shivaji V. More、Wen-Shan Li

  DOI：10.1016/j.mencom.2014.04.011

  日期：2014.5

  Dibenzo[b,f]azocin-6(5H)-one and dibenzo[b,g]azonin-6(13H)-one were prepared in five steps from methyl 4-amino-3-iodobenzoate.