N-五氟苯基萘-2-甲酰胺 | 1020208-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-五氟苯基萘-2-甲酰胺
• 英文名称: N-pentafluorophenylnaphthalene-2-carboxamide
• 英文别名: N-(perfluorophenyl)-2-naphthamide
• CAS: 1020208-06-3
• 化学式: C₁₇H₈F₅NO
• 分子量: 337.249
• InChiKey: IRTQOPXCQGZRSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-五氟苯基萘-2-甲酰胺 在 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Fluorinated Bis(phenoxyketimine)titanium Complexes for the Living, Isoselective Polymerization of Propylene:  Multiblock Isotactic Polypropylene Copolymers via Sequential Monomer Addition

  摘要：

  A series of bis(phenoxyketimine)titanium dichloride complexes were synthesized and evaluated as catalysts for living, isoselective propylene polymerization upon activation with methylaluminoxane (MAO). Catalysts bearing phenoxyketimine ligands with different substituents at the ortho and para. positions of the phenolate ring and substituents at the ketimine carbon were investigated. The identity of the ketimine substituent had the largest effect on the activity and isoselectivity of propylene polymerization. Complex 12/MAO promoted the living, isoselective polymerization of propylene ([m(4)] = 0.73, alpha = 0.94). This catalyst system was used for the synthesis of a number of block copolymers featuring isotactic polypropylene semicrystalline blocks and poly(ethylene-co-propylene) amorphous blocks. Several triblock samples with varying block lengths, a pentablock, and a heptablock copolymer were synthesized. Mechanical testing has revealed that each is elastomeric with elongations at break between similar to 790-1000%.

  DOI：

  10.1021/ja077772g
• 作为产物：
  描述：

  2-萘甲酸 在 草酰氯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N-五氟苯基萘-2-甲酰胺
  参考文献：
  名称：

  配体促进的RhIII催化的苯甲酰胺具有广泛的二硫键范围的硫醇化作用

  摘要：

  已经开发了配体促进的Rh III催化苯甲酰胺的C（sp 2）-H活化/硫醇化。使用双齿单-N-保护的氨基酸配体导致了第一个由弱配位的直接酰胺基团指导的Rh III催化的芳基硫醇化反应的例子。该反应可耐受各种酰胺和二硫化物试剂。

  DOI：

  10.1002/anie.201903511

文献信息

• Ligand-Promoted Rh(III)-Catalyzed Coupling of Aryl C–H Bonds with Arylboron Reagents
  作者：Huai-Wei Wang、Pei-Pei Cui、Yi Lu、Wei-Yin Sun、Jin-Quan Yu

  DOI：10.1021/acs.joc.6b00083

  日期：2016.4.15

  Rhodium(III)-catalyzed C–H arylation of arenes with phenylboronic acid pinacol esters has been achieved using a readily removable N-pentafluorophenylbenzamide directing group for the first time. The use of a bidentate phosphine ligand (Binap) significantly increased the yield of the cross-coupling of C–H bonds with organoboron reagents.

  铑（III）催化的芳烃与苯基硼酸频哪醇酯的C–H芳基化反应是首次使用易于去除的N-五氟苯基苯甲酰胺直接基团实现的。使用双齿膦配体（Binap）可显着提高C–H键与有机硼试剂交叉偶联的产率。
• Ligand‐Promoted Rhodium(III)‐Catalyzed <i>ortho</i> ‐C−H Amination with Free Amines
  作者：Huai‐Wei Wang、Yi Lu、Bing Zhang、Jian He、Hua‐Jin Xu、Yan‐Shang Kang、Wei‐Yin Sun、Jin‐Quan Yu

  DOI：10.1002/anie.201703300

  日期：2017.6.19

  Ligand development for rhodium(III)‐catalyzed C−H activation reactions has largely been limited to cyclopentadienyl (Cp) based scaffolds. 2‐Methylquinoline has now been identified as a feasible ligand that can coordinate to the metal center of Cp*RhCl to accelerate the cleavage of the C−H bond of N‐pentafluorophenylbenzamides, providing a new structural lead for ligand design. The compatibility of

  铑（III）催化的CH活化反应的配体形成主要限于基于环戊二烯基（Cp）的支架。现已确定2-甲基喹啉是一种可行的配体，它可以与Cp * RhCl的金属中心配位，以加速N-五氟苯基苯甲酰胺的C-H键的裂解，为配体设计提供了新的结构线索。该反应与仲游离胺和苯胺的相容性还克服了钯（II）催化的CH氨基化反应的局限性。