N,N-dimethyl-2-(phenylamino)benzamide | 935688-11-2

• 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: N,N-dimethyl-2-(phenylamino)benzamide
• 英文别名: 2-anilino-N,N-dimethylbenzamide
• CAS: 935688-11-2
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: VWOZJXJSFSCMMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-(phenylamino)benzamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到2-((dimethylamino)methyl)-N-phenylaniline
  参考文献：
  名称：

  紧密相关的联苯二胺膦骨架及其锆和Ha配合物：配体的微小变化导致不同的配合物稳定性和反应性

  摘要：

  The closely related benzylene-linked diaminophosphines PhP(CH2C6H4-o-NHPh)(2) ([(Ph)A]H-2) and PhP(C6H4-o-CH(2)NHXyl)(2) ( [B]H-2) were prepared as robust alternatives to the previously reported N,N'-bis(trimethylsilyl)substituted derivative PhP(CH2C6H4-o-NHSiMe3)(2) ([(Si)A]H-2). Upon reaction of [(Ph)A]H-2 and [B]H-2 with M(NMe2)(4) (M = Zr, Hf), the respective dimethylamido complexes [PhA]M(NMe2)2 and [B]M(NMe2)(2) ([(Ph)A]-1-M and [B]-1-M, M = Zr, Hf) were isolated in high yields and converted to the corresponding diiodo derivatives [(Ph)A]MI2 and [B]MI2 ([(Ph)A]-2-M and [B]-2-M, M = Zr, Hf). In contrast to [(Si)A]ZrI2, these thermally robust diiodo complexes were found to react cleanly with Bn2MgL2 (L = THE or Et2O), resulting in the corresponding dibenzyl species [(Ph)A]MBn2 and [B]MBn2 ([(Ph)A]-4-M and [B]-4-M, M = Zr, Hf). Upon addition of [B]H-2 to [B]ZrBn2, the related homoleptic species [B](2)Zr ([B]-5-Zr) was generated. Similar 2:1 complexes have not been observed for the hafnium homologue bearing the latter ligand or for [(Si)A]- [(Ph)A]-coordinated complexes. The former dibenzyl complexes were reacted with 2,6-xylylisonitrile, and clean conversions to the bis-eta(2)-iminoacyl complexes [B]-6-Hf and [(Ph)A]-6-M were observed for [B]-4-Hf and [(Ph)A]-4-M (M = Zr, Hf). For [(Si)A]HfBn2 ([(Si)A]-4-Hf) only one equivalent of the former isonitrile was inserted into one of the hafnium carbon bonds, which is in line with the steric differences between [(Si)A] and [(Ph)A].

  DOI：

  10.1021/acs.organomet.6b00384

文献信息

• Closely Related Benzylene-Linked Diamidophosphine Scaffolds and Their Zirconium and Hafnium Complexes: How Small Changes of the Ligand Result in Different Complex Stabilities and Reactivities
  作者：Sonja Batke、Malte Sietzen、Lukas Merz、Hubert Wadepohl、Joachim Ballmann

  DOI：10.1021/acs.organomet.6b00384

  日期：2016.7.11

  The closely related benzylene-linked diaminophosphines PhP(CH2C6H4-o-NHPh)(2) ([(Ph)A]H-2) and PhP(C6H4-o-CH(2)NHXyl)(2) ( [B]H-2) were prepared as robust alternatives to the previously reported N,N'-bis(trimethylsilyl)substituted derivative PhP(CH2C6H4-o-NHSiMe3)(2) ([(Si)A]H-2). Upon reaction of [(Ph)A]H-2 and [B]H-2 with M(NMe2)(4) (M = Zr, Hf), the respective dimethylamido complexes [PhA]M(NMe2)2 and [B]M(NMe2)(2) ([(Ph)A]-1-M and [B]-1-M, M = Zr, Hf) were isolated in high yields and converted to the corresponding diiodo derivatives [(Ph)A]MI2 and [B]MI2 ([(Ph)A]-2-M and [B]-2-M, M = Zr, Hf). In contrast to [(Si)A]ZrI2, these thermally robust diiodo complexes were found to react cleanly with Bn2MgL2 (L = THE or Et2O), resulting in the corresponding dibenzyl species [(Ph)A]MBn2 and [B]MBn2 ([(Ph)A]-4-M and [B]-4-M, M = Zr, Hf). Upon addition of [B]H-2 to [B]ZrBn2, the related homoleptic species [B](2)Zr ([B]-5-Zr) was generated. Similar 2:1 complexes have not been observed for the hafnium homologue bearing the latter ligand or for [(Si)A]- [(Ph)A]-coordinated complexes. The former dibenzyl complexes were reacted with 2,6-xylylisonitrile, and clean conversions to the bis-eta(2)-iminoacyl complexes [B]-6-Hf and [(Ph)A]-6-M were observed for [B]-4-Hf and [(Ph)A]-4-M (M = Zr, Hf). For [(Si)A]HfBn2 ([(Si)A]-4-Hf) only one equivalent of the former isonitrile was inserted into one of the hafnium carbon bonds, which is in line with the steric differences between [(Si)A] and [(Ph)A].