N¹,N¹-diisopropyl-N²-(3-phenylpropyl)oxalamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N¹,N¹-diisopropyl-N²-(3-phenylpropyl)oxalamide
• 英文别名: N-(3-phenylpropyl)-N',N'-di(propan-2-yl)oxamide
• 化学式: C₁₇H₂₆N₂O₂
• 分子量: 290.406
• InChiKey: LATLQGIYXWKKTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N¹,N¹-diisopropyl-N²-(3-phenylpropyl)oxalamide 在 碘苯二乙酸 、 palladium diacetate 作用下， 反应 24.0h， 以82%的产率得到N,N-diisopropyl-2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoacetamide
  参考文献：
  名称：

  钯催化的C（sp2）分子内胺化的辅助助剂是否容易获得？H和C（sp3）？δ和ε位置的H键

  摘要：

  已经开发了一种易于合成且易于获得的N，O-双齿状助剂，用于在钯催化下选择性CH活化。新颖的辅助显示用C其第一强大的应用远程位置h的官能化。两个C（SP 2） H和C（SP 3） H在δ-和ε位键被有效激活，由此得到四氢喹啉，benzomorpholines，吡咯烷，二氢吲哚并在中度至通过钯催化的分子内Ç优异的产率氨化。

  DOI：

  10.1002/anie.201404854
• 作为产物：
  描述：

  N,N-diisopropyloxamoyl chloride 在 palladium diacetate 、 三乙胺 、 silver carbonate 作用下， 以 二氯甲烷 、 均三甲苯 为溶剂， 反应 42.0h， 生成 N¹,N¹-diisopropyl-N²-(3-phenylpropyl)oxalamide
  参考文献：
  名称：

  Palladium-Catalyzed Oxalyl Amide-Directed γ-Arylation of Aliphatic Amines

  摘要：

  A method for palladium-catalyzed oxalyl amide-directed arylation of alpha-unsubstituted aliphatic amines with aryl iodides has been developed. A wide variety of aryl iodides are tolerated in this transformation, affording various gamma-arylpropylamine derivatives. Heterocyclic iodides can also be competent reagents in this gamma-C(sp(3))-H bonds transformation.

  DOI：

  10.1021/acs.joc.5b00968

文献信息

• Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp²)H and C(sp³)H Bonds at δ- and ε-Positions
  作者：Chao Wang、Changpeng Chen、Jingyu Zhang、Jian Han、Qian Wang、Kun Guo、Pei Liu、Mingyu Guan、Yingming Yao、Yingsheng Zhao

  DOI：10.1002/anie.201404854

  日期：2014.9.8

  for selective CH activation under palladium catalysis. The novel auxiliary showed its first powerful application in CH functionalization of remote positions. Both C(sp2)H and C(sp3)H bonds at δ‐ and ε‐positions were effectively activated, thus giving tetrahydroquinolines, benzomorpholines, pyrrolidines, and indolines in moderate to excellent yields by palladium‐catalyzed intramolecular CH amination

  已经开发了一种易于合成且易于获得的N，O-双齿状助剂，用于在钯催化下选择性CH活化。新颖的辅助显示用C其第一强大的应用远程位置h的官能化。两个C（SP 2） H和C（SP 3） H在δ-和ε位键被有效激活，由此得到四氢喹啉，benzomorpholines，吡咯烷，二氢吲哚并在中度至通过钯催化的分子内Ç优异的产率氨化。
• Highly site-selective sequential alkenylation of oxalyl amide protected phenylpropylamine derivatives via a seven-membered palladacycle
  作者：Qian Wang、Jian Han、Chao Wang、Jingyu Zhang、Zhibin Huang、Daqing Shi、Yingsheng Zhao

  DOI：10.1039/c4sc02172j

  日期：——

  A protocol for palladium-catalyzed ortho C(sp2)–H alkenylation via a rarely reported seven-membered palladacycle with oxalyl amide as a directing group was reported. The range of olefins was the broadest yet reported for this kind of C–H alkenylation reaction. For example, allyl acetate, allyl alcohol derivatives, acraldehyde, acrylate and acrylonitrile were all tolerated in this C–H transformation. Sequential alkenylation reactions were also achieved to construct the complex olefinated arenes in good yields in one pot.

  报道了一种通过罕见的七元钯杂环和草酰胺作为导向基团的钯催化的邻位C(sp²)–H烯基化反应协议。对于这类C–H烯基化反应，这是报道的烯烃范围最广泛的一次。例如，丙烯酸酯、丙烯醇衍生物、丙醛、丙烯酸酯和丙烯腈都在这个C–H转化中得到耐受。序贯烯基化反应也实现了在一锅中高效构建复杂的烯化芳烃。
• Palladium-catalyzed oxalyl amide assisted direct ortho-alkynylation of arylalkylamine derivatives at δ and ε positions
  作者：Mingyu Guan、Changpeng Chen、Jingyu Zhang、Runsheng Zeng、Yingsheng Zhao

  DOI：10.1039/c5cc04390e

  日期：——

  Palladium-catalyzed oxalyl amide directed ortho-alkynylation of arylalkylamine derivatives via rare six- and seven-membered palladacycles has been reported.

  钯催化的以草酸酰胺为导向的芳基烷基胺衍生物的邻位炔基化反应，通过罕见的六元和七元钯环已经报道。
• Palladium-Catalyzed Oxalyl Amide-Directed γ-Arylation of Aliphatic Amines
  作者：Jian Han、Yongxiang Zheng、Chao Wang、Yan Zhu、Da-Qing Shi、Runsheng Zeng、Zhi-Bin Huang、Yingsheng Zhao

  DOI：10.1021/acs.joc.5b00968

  日期：2015.9.18

  A method for palladium-catalyzed oxalyl amide-directed arylation of alpha-unsubstituted aliphatic amines with aryl iodides has been developed. A wide variety of aryl iodides are tolerated in this transformation, affording various gamma-arylpropylamine derivatives. Heterocyclic iodides can also be competent reagents in this gamma-C(sp(3))-H bonds transformation.
• Highly efficient synthesis of indoline via palladium catalyzed C–H amination of C(sp2)–H bond using tert-butyl peroxybenzoate as an oxidant
  作者：Wei Lin、Xiu-Xiu Hu、Jian Han、Guo-Bin Liang

  DOI：10.1016/j.tet.2022.133206

  日期：2023.3