(E)-methyl 3-(2-(dimethylamino)phenyl)acrylate | 1292323-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 3-(2-(dimethylamino)phenyl)acrylate
• 英文别名: methyl (E)-3-[2-(dimethylamino)phenyl]prop-2-enoate
• CAS: 1292323-48-8
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: JLABBBHKZQXUNV-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(2-(dimethylamino)phenyl)acrylate 在 sodium tetrahydroborate 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 溶剂黄146 、 sodium sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

  摘要：

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

  DOI：

  10.1021/ja110766a
• 作为产物：
  描述：

  2-二甲氨基苯甲酸甲酯 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-methyl 3-(2-(dimethylamino)phenyl)acrylate
  参考文献：
  名称：

  Emission Wavelength Prediction of a Full-Color-Tunable Fluorescent Core Skeleton, 9-Aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one

  摘要：

  In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.

  DOI：

  10.1021/ja110766a

文献信息

• <i>N</i>-Oxide as a Traceless Oxidizing Directing Group: Mild Rhodium(III)-Catalyzed CH Olefination for the Synthesis of<i>ortho</i>-Alkenylated Tertiary Anilines
  作者：Xiaolei Huang、Jingsheng Huang、Chenglong Du、Xingyi Zhang、Feijie Song、Jingsong You

  DOI：10.1002/anie.201307174

  日期：2013.12.2

  Double role: A traceless directing group also acts as an internal oxidant in a novel RhIII‐catalyzed protocol developed for the synthesis of ortho‐alkenylated tertiary anilines (see scheme). A five‐membered cyclometalated RhIII complex is proposed as a plausible intermediate and confirmed by X‐ray crystallographic analysis.

  双重作用：在为合成邻链烯基化叔苯胺而开发的新型Rh III催化方案中，无痕导向基团还充当内部氧化剂（参见方案）。一种五元环金属化的Rh III配合物被认为是可行的中间体，并通过X射线晶体学分析得到了证实。
• HONG, PANGBU;MISE, TAKAYA;YAMAZAKI, HIROSHI, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1985, N 3, 479-485
  作者：HONG, PANGBU、MISE, TAKAYA、YAMAZAKI, HIROSHI

  DOI：——

  日期：——