4-(tert-butyl)-N-phenylbenzimidamide | 1352641-99-6

• 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: 4-(tert-butyl)-N-phenylbenzimidamide
• 英文别名: N-phenyl-4-tert-butylbenzamidine；4-tert-butyl-N'-phenylbenzenecarboximidamide
• CAS: 1352641-99-6
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: AVFHDUFKTQYEKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(tert-butyl)-N-phenylbenzimidamide 在 N-碘代丁二酰亚胺 、 三氟化硼乙醚 、 氧气 、 palladium diacetate 、 potassium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(4-(tert-butyl)-2,6-diiodophenyl)quinazoline
  参考文献：
  名称：

  喹唑啉通过 Pd(II) 催化的 C(sp2)-H 活化与 N-卤代琥珀酰亚胺进行邻位卤化

  摘要：

  本文描述了使用N-卤代琥珀酰亚胺作为卤素源的钯 (II) 催化的 2-苯基喹唑啉卤化反应，该反应通过 C-H 活化在温和的反应条件下进行。通过 C-H 官能化合成了一系列卤素取代的 2-芳基喹唑啉。

  DOI：

  10.1002/ejoc.202200316
• 作为产物：
  描述：

  4-叔丁基苄腈 、 苯胺 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 0.25h， 生成 4-(tert-butyl)-N-phenylbenzimidamide
  参考文献：
  名称：

  喹唑啉通过 Pd(II) 催化的 C(sp2)-H 活化与 N-卤代琥珀酰亚胺进行邻位卤化

  摘要：

  本文描述了使用N-卤代琥珀酰亚胺作为卤素源的钯 (II) 催化的 2-苯基喹唑啉卤化反应，该反应通过 C-H 活化在温和的反应条件下进行。通过 C-H 官能化合成了一系列卤素取代的 2-芳基喹唑啉。

  DOI：

  10.1002/ejoc.202200316

文献信息

• A one-pot process for synthesis of eight-membered cyclopalladated amidines via cascade C H activation and insertion
  作者：Fen Xu、Yuan-Yuan Song、Hui-Min Zhou、Chun-Sen Liu、Ya-Zhou Lu、Jun-Ping Du

  DOI：10.1016/j.jorganchem.2020.121461

  日期：2020.10

  one-pot process involving cascade C-H activation and insertion between amidines and alkynes in the presence of palladium salt is described. With this methodology, various novel eight-membered cyclopalladated amidines were efficiently constructed. Notably, a series of functionalities with potential application were readily accommodated under the reaction conditions. Isotope effects and H/D exchange

  描述了一种一锅法，该方法涉及在钯盐存在下级联CH活化和am与炔之间的插入。用这种方法，可以有效地构建各种新颖的八元环palpalated idine。值得注意的是，在反应条件下容易适应一系列具有潜在应用的功能。同位素效应和H / D交换表明，这种级联反应是由am的N-苯基环中的邻位CH键断裂而引发的。
• Rhodium(III)‐Catalyzed Oxidative Annulation of Amidines with Alkynes <i>via</i> Sequential C−H Bond Activation
  作者：Yan‐Yu Meng、Wen‐Jing Zhu、Yuan‐Yuan Song、Gang‐Gang Bu、Li‐Juan Zhang、Fen Xu

  DOI：10.1002/ejoc.202001634

  日期：2021.2.25

  The first rhodium‐catalyzed oxidative double C−H activation/annulation reaction of amidines and alkynes to construct benzimidazoisoquinolines was developed. The operationally simple transformation showed high functional group compatibility and featured the cleavage of the C−H bonds located on a different moiety of the N‐phenylbenzimidamide substrates.

  研发了第一个铑催化的s和炔烃双氧化C / H活化/环化反应，以构建苯并咪唑并异喹啉。操作上简单的转化显示出高官能团相容性，并具有位于N-苯基苯并咪唑底物不同部分的CH键断裂的特征。
• Manganese‐Catalyzed <i>ortho‐</i> Alkenylation of Aromatic Amidines with Alkynes via C−H Activation
  作者：Teng Jia、Congyang Wang

  DOI：10.1002/cctc.201900387

  日期：2019.11.7

  The first ortho‐alkenylation of aromatic amidines with alkynes was realized by earth‐abundant manganese catalysis through C−H activation. A catalytic amount of PhMgBr was found essential for improved efficiency of this transformation. Wide tolerance of functional groups and excellent E/Z selectivity highlighted the current protocol.

  芳香族idine与炔烃的第一个邻位烯基化是通过C–H活化富于地球的锰催化实现的。发现催化量的PhMgBr对于提高该转化效率是必不可少的。官能团的宽容度和出色的E / Z选择性突出了当前方案。
• Rhodium-catalyzed multiple C–H activation/highly<i>meta</i>-selective C–H amination between amidines and alkynes
  作者：Fen Xu、Yuan-Yuan Song、Wen-Jing Zhu、Chun-Sen Liu、Ya-Zhou Lu、Miao Du

  DOI：10.1039/d0cc04885b

  日期：——

  A tandem process of multiple C–H activation and intermolecular highly meta-selective C–H amination between amidines and alkynes has been developed. Mechanistic studies demonstrate that the reaction is proposed to proceed through two different Rh(I)–Rh(III) catalytic cycles, wherein Rhodium-complex I and Rhodacycle intermediate II were isolated for the first time.

  多个C-H活化和分子间高度的串接处理的元脒和炔烃之间-选择性C-H的胺化得到了发展。机理研究表明，建议该反应通过两个不同的Rh（I）-Rh（III）催化循环进行，其中首次分离了铑配合物I和Rhodacycle中间体II。
• Reactions of N-Monosubstituted Amidines with AlMe₃ and AlMeCl₂: Formation of Fused Triazaalane Heterocycles
  作者：K. Maheswari、N. Dastagiri Reddy

  DOI：10.1021/om2007375

  日期：2012.1.9

  Reactions of N-monosubstituted amidines of the formula HN=C(R) NH(R') (R = Ph, 4-tert-butylphenyl, Me; R' = 2,6-dlisopropylphenyl, Ph) with AlMe3 and AlMeCl2 are reported. All the N-(Dipp)amidines (Dipp = 2,6-diisopropylphenyl) react with AlMe3 in a 1:1 ratio to yield tetrameric aluminum amidinates (1, 2, and 3) in good yields. In these compounds, the amidinate ligand chelates to Al while bridging to another Al. However, when N-phenylamidines are employed, tetracyclic (4-9) and pentacyclic (10) Al-N-C heterocycles are formed. In the case of N-phenylbenzamidine, formation of a hexacyclic Al-N-C heterocycle (11) is observed when a slight excess of AlMe3 (1:1.2 equiv) is used. In these compounds, the amidinate ligand coordinates to Al atoms in a bridging fashion, Further, N-(Dipp)acetamidine and N-(Dipp)benzamidine are also treated with AlMeCl2. Whereas N-(Dipp)acetamidine affords an ionic 15-membered aluminum amidinate chain (12), N-(Dipp)benzamidine gives a bicyclic heterocycle (13) and the AlCl3 adduct of N-(Dipp)benzamidine (14). However, from a reaction between N-phenylbenzamidine and AlMeCl2, only the AlC13 adduct, 15, was isolated. Compounds 3, 4, 6, 8, and 10-15 have been structurally characterized.