2-methyl-N-phenethylprop-2-en-1-amine

• 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-methyl-N-phenethylprop-2-en-1-amine
• 英文别名: 2-methyl-N-(2-phenylethyl)prop-2-en-1-amine
• 化学式: C₁₂H₁₇N
• mdl: MFCD16471988
• 分子量: 175.274
• InChiKey: XWLMQRWQFRZTJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-N-phenethylprop-2-en-1-amine 、 丙烯酸乙酯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以75%的产率得到ethyl 2-(4-methyl-1-phenethyl-1H-pyrrol-2-yl)acetate
  参考文献：
  名称：

  Synthesis of Pyrroles through Rhodium(III)-Catalyzed Reactions of Allylamines and Alkenes

  摘要：

  Pyrrole derivatives are generated in reactions of allylamines with alkenes that are promoted by a Rh(III) catalyst in the presence of AgOAc. This process, which involves chelation assisted C-H bond activation and N-annulation, is applied to a three step synthesis of Zomepirac.

  DOI：

  10.1021/acs.orglett.5b01811

文献信息

• Synthesis of Benzoquinolizinium Salts by Rh(III)-Catalyzed Cascade Double <i>N</i>-Annulation Reactions of Allylamines, Diarylacetylenes, and HBF₄
  作者：Ye Ri Han、Su-Hyang Shim、Dong-Su Kim、Chul-Ho Jun

  DOI：10.1021/acs.orglett.7b01175

  日期：2017.6.2

  A new cascade double N-annulation method has been developed for the synthesis of benzoquinolizinium salts. The process takes place between allylamines, internal alkynes, and HBF4 in the presence of Rh(III)/Cu(II) complexes and leads to formation of multisubstituted benzoquinolizinium salts. Importantly, the resulting benzoquinolizinium salts serve as fluorescent materials whose emission wavelengths

  已经开发了一种新的级联双N-环化方法来合成苯并喹啉鎓盐。该过程在Rh（III）/ Cu（II）络合物的存在下，在烯丙胺，内部炔烃和HBF 4之间进行，并导致形成多取代的苯并喹啉鎓盐。重要的是，所得的苯并喹啉鎓盐用作荧光材料，其发光波长可通过选择合适的取代基来调节。
• Medical fluorophore 1 (MF1), a benzoquinolizinium-based fluorescent dye, as an inflammation imaging agent
  作者：Sang Bong Lee、Ye Ri Han、Hui-Jeon Jeon、Chul-Ho Jun、Sang-Kyoon Kim、Jungwook Chin、Su-Jeong Lee、Minseon Jeong、Jae-Eon Lee、Chang-Hee Lee、Sung Jin Cho、Dong-Su Kim、Yong Hyun Jeon

  DOI：10.1039/c9tb01266d

  日期：——

  Structure-based targeting of fluorescent dyes is essential for their use as imaging agents for disease diagnosis. Here, we describe the development of the benzoquinolizinium compound Medical fluorophore 1 (MF1) as a novel biomedical imaging agent that allows the visualization of inflammation by virtue of its unique chemical structure. Lipopolysaccharide treatment stimulated the uptake of MF1 by bone

  荧光染料的基于结构的靶向对于将其用作疾病诊断的成像剂至关重要。在这里，我们描述了作为一种新型生物医学成像剂的苯并喹啉鎓化合物医用荧光团1（MF1）的开发，该试剂凭借其独特的化学结构可实现炎症的可视化。脂多糖处理刺激了骨髓来源的巨噬细胞对MF1的吸收，而对细胞增殖没有不利影响。体内荧光寿命成像显示在角叉菜胶诱导的小鼠急性炎症性病变中MF1的积累在6 h达到峰值。基于MF1的成像还可以监测对消炎药地塞米松和柳氮磺吡啶的反应。因此，MF1可用于诊断以炎症和治疗功效为特征的疾病。
• Pyridinium Salt Forming Rh(III)-Catalyzed Annulation Reaction of Secondary Allylamines with Internal Alkynes and Its Application to Surface Modification of a Mesoporous Material
  作者：Ye Ri Han、Su-Hyang Shim、Dong-Su Kim、Chul-Ho Jun

  DOI：10.1021/acs.orglett.7b03654

  日期：2018.1.5

  A Rh(III)-catalyzed C H activation reaction has been developed for the preparation of pyridinium salts from secondary allylamines and internal alkynes. The pyridinium salts formed by this N-annulation reaction have interesting fluorescence properties. This protocol has been applied to the surface modification of mesoporous silica materials to generate functionalized silica that can be used for the detection of nitrobenzene.
• Synthesis of Pyrroles through Rhodium(III)-Catalyzed Reactions of Allylamines and Alkenes
  作者：Dong-Su Kim、Yong-Sik Seo、Chul-Ho Jun

  DOI：10.1021/acs.orglett.5b01811

  日期：2015.8.7

  Pyrrole derivatives are generated in reactions of allylamines with alkenes that are promoted by a Rh(III) catalyst in the presence of AgOAc. This process, which involves chelation assisted C-H bond activation and N-annulation, is applied to a three step synthesis of Zomepirac.