2-(benzylamino)-6-methylbenzonitrile | 1221594-06-4

• 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: 2-(benzylamino)-6-methylbenzonitrile
• 英文别名: 2-(Benzylamino)-6-methylbenzonitrile
• CAS: 1221594-06-4
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: MNYUJZPMBRLZNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 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：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzylamino)-6-methylbenzonitrile 、 甲基溴化镁 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以68%的产率得到1-[2-(Benzylamino)-6-methylphenyl]ethanone
  参考文献：
  名称：

  Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation

  摘要：

  The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.073
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以4.99 g的产率得到2-(benzylamino)-6-methylbenzonitrile
  参考文献：
  名称：

  Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation

  摘要：

  The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.073

文献信息

• Borrowing Hydrogen Methodology for N-Benzylation using a π-Benzylpalladium System in Water
  作者：Hidemasa Hikawa、Toshitaka Koike、Kyoko Izumi、Shoko Kikkawa、Isao Azumaya

  DOI：10.1002/adsc.201501041

  日期：2016.3.3

  We demonstrate a borrowing hydrogen methodology using the unique reactivity of the π‐benzylpalladium system in water, which offers an efficient and environmentally friendly N‐monobenzylation of electron‐deficient anilines or 2‐aminopyridine with non‐activated benzylic alcohols under neutral conditions. The crossover experiment using benzyl‐α,α‐d2 alcohol and 3‐methylbenzyl alcohol afforded H/D scrambling

  我们使用π-苄基钯体系在水中的独特反应性证明了借用氢法的方法，该方法可在中性条件下利用非活化苄醇对缺电子的苯胺或2-氨基吡啶进行N-单苄基化反应，实现高效环保。使用苄基α，α-交叉实验d 2醇和得到H / d加扰的产品，这表明发生在我们的催化体系的借款氢途径3-甲基苄基醇。我们的简单方案可以完成2-氨基苄腈的克级反应（分离产率为76％），并且仅使用1 mol％的Pd（OAc）2和2 mol％的TPPMS进行反应，而无需在水中添加其他添加剂。
• Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation
  作者：Yoshizumi Yasui、Haruhi Kamisaki、Takayuki Ishida、Yoshiji Takemoto

  DOI：10.1016/j.tet.2010.01.073

  日期：2010.3

  The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.