N-phenyl-1-(p-methoxyphenyl)-2-propenylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-phenyl-1-(p-methoxyphenyl)-2-propenylamine
• 英文别名: N-[(1R)-1-(4-methoxyphenyl)prop-2-enyl]aniline
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: FGBKGEGXPPJHNT-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(p-methoxyphenyl)-2-propen-1-yl methyl carbonate 、 苯胺 在 正丙胺 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 (2S)-1-(2,6-diphenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-2-methyl-1,2,3,4-tetrahydroquinoline 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以80%的产率得到N-phenyl-1-(p-methoxyphenyl)-2-propenylamine
  参考文献：
  名称：

  铱催化的N-芳基亚磷酰胺配体的不对称烯丙基胺化反应

  摘要：

  A series of N-aryl phosphoramidite ligands were synthesized, and the iridium complexes derived from these novel ligands were proven to be efficient catalysts for asymmetric intermolecular allylic amination reactions. This C-N bond forming process readily accommodates a diverse range of amines and allylic carbonates, especially for the previously challenging ortho-substituted cinnamyl substrates. Moreover, isolation and characterization of the corresponding (pi-allyl)-iridium complex K1 reveal that the active iridacycle is generated through a C(sp(2))-H bond insertion of tetrahydroquinoline of the ligand.

  DOI：

  10.1021/acs.organomet.6b00339

文献信息

• Iridium-Catalyzed, Asymmetric Amination of Allylic Alcohols Activated by Lewis Acids
  作者：Yasuhiro Yamashita、Apsara Gopalarathnam、John F. Hartwig

  DOI：10.1021/ja0730718

  日期：2007.6.1

  enantioselective amination of allylic alcohols with Lewis acid activators to form branched allylic amine products is reported. The reactions of arylamines, benzylic amines, and secondary aliphatic amines in the presence of Nb(OEt)5 as activator occurred with high regioselectivities and high enantioselectivities. These results led to the development of Ir-catalyzed reactions of allylic alcohol with arylamines

  报道了烯丙醇与路易斯酸活化剂的直接、Ir 催化、区域和对映选择性胺化反应，形成支链烯丙胺产物。在 Nb(OEt)5 作为活化剂存在下，芳胺、苄胺和脂肪仲胺的反应具有高区域选择性和高对映选择性。这些结果导致了烯丙醇与芳胺和 BPh3 作为催化量的活化剂的 Ir 催化反应的发展。这些反应是烯丙醇对映选择性取代的罕见例子。它们是烯丙醇取代以从单取代烯丙醇产生支化取代产物以及烯丙醇与胺亲核试剂的对映选择性取代的特别不寻常的例子。
• Iridium-Catalyzed Asymmetric Allylic Amination Reactions with <i>N</i>-Aryl Phosphoramidite Ligands
  作者：Xiao Zhang、Wen-Bo Liu、Qiang Cheng、Shu-Li You

  DOI：10.1021/acs.organomet.6b00339

  日期：2016.8.8

  A series of N-aryl phosphoramidite ligands were synthesized, and the iridium complexes derived from these novel ligands were proven to be efficient catalysts for asymmetric intermolecular allylic amination reactions. This C-N bond forming process readily accommodates a diverse range of amines and allylic carbonates, especially for the previously challenging ortho-substituted cinnamyl substrates. Moreover, isolation and characterization of the corresponding (pi-allyl)-iridium complex K1 reveal that the active iridacycle is generated through a C(sp(2))-H bond insertion of tetrahydroquinoline of the ligand.