N-ethyl-N-methyl-1,3-diphenylprop-2-yn-1-amine | 1206905-71-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-ethyl-N-methyl-1,3-diphenylprop-2-yn-1-amine
• CAS: 1206905-71-6
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: WBETUKPHBXCHKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-methyl-1,3-diphenylprop-2-yn-1-amine 在 potassium fluoride 、 二氟溴乙酸乙酯 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.0h， 生成 (1-(4-methoxyphenyl)propa-1,2-diene-1,3-diyl)dibenzene
  参考文献：
  名称：

  脂肪族叔胺与芳基和烯基硼酸通过氮叶立德的脱氨基芳基化和烯基化

  摘要：

  在无过渡金属的条件下，二氟卡宾能够实现叔胺与芳基和烯基硼酸的有效且通用的脱氨芳基化和烯基化。该协议代表了一种新的反应模式，它通过叔胺（炔丙基胺、烯丙基胺和 1H-吲哚-3-基甲烷胺）和二氟卡宾原位形成的氮叶立德成功地构建了 C sp 3 -C sp 2键与芳基和烯基硼酸。

  DOI：

  10.1002/anie.202212740
• 作为产物：
  描述：

  N-Methylalanin 、 苯甲醛 、 苯乙炔 在 copper(l) iodide 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 N-ethyl-N-methyl-1,3-diphenylprop-2-yn-1-amine 、 N-benzyl-N-methyl-4-phenylbut-3-yn-2-amine
  参考文献：
  名称：

  Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp³−Csp) of Natural α-Amino Acids and Alkynes

  摘要：

  An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO2 and H2O as the only by products. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.

  DOI：

  10.1021/jo902319h

文献信息

• Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp³−Csp) of Natural α-Amino Acids and Alkynes
  作者：Hai-Peng Bi、Qingfeng Teng、Min Guan、Wen-Wen Chen、Yong-Min Liang、Xiaojun Yao、Chao-Jun Li

  DOI：10.1021/jo902319h

  日期：2010.2.5

  An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO2 and H2O as the only by products. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.
• Deaminative Arylation and Alkenyaltion of Aliphatic Tertiary Amines with Aryl and Alkenylboronic Acids via Nitrogen Ylides
  作者：Jianke Su、Chengbo Li、Xinyuan Hu、Yu Guo、Qiuling Song

  DOI：10.1002/anie.202212740

  日期：2022.12.23

  arylation and alkenylation of tertiary amines with aryl and alkenylboronic acids is enabled by difluorocarbene under transition-metal-free conditions. This protocol represents a novel reaction mode which succeeded in the construction of Csp3−Csp2 bonds via an in situ formed nitrogen ylide from tertiary amines (propargyl amines, allyl amines and 1H-indol-3-yl methane amines) and difluorocarbene with aryl and

  在无过渡金属的条件下，二氟卡宾能够实现叔胺与芳基和烯基硼酸的有效且通用的脱氨芳基化和烯基化。该协议代表了一种新的反应模式，它通过叔胺（炔丙基胺、烯丙基胺和 1H-吲哚-3-基甲烷胺）和二氟卡宾原位形成的氮叶立德成功地构建了 C sp 3 -C sp 2键与芳基和烯基硼酸。