4-[2-(N-methylanilino)acetyl]benzonitrile | 1152856-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2-(N-methylanilino)acetyl]benzonitrile
• CAS: 1152856-68-2
• 化学式: C₁₆H₁₄N₂O
• mdl: MFCD12495521
• 分子量: 250.3
• InChiKey: JFHYCCQIMYGCEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(N-methylanilino)acetyl]benzonitrile 反应 0.67h， 以73%的产率得到4-(1-methyl-1H-indol-3-yl)benzonitrile
  参考文献：
  名称：

  微波辐射下 HFIP 促进的 Bischler 吲哚合成

  摘要：

  发现 1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) 在没有金属催化剂的情况下在微波辐射下对 Bischler 吲哚合成有效。在HFIP的催化下，广泛的α-氨基芳基丙酮成功地转化为吲哚衍生物，产率中等至良好。

  DOI：

  10.3390/molecules23123317

文献信息

• Rearrangement of 3-Hydroxyazetidines into 2-Oxazolines
  作者：Michele Ruggeri、Amanda W. Dombrowski、Stevan W. Djuric、Ian R. Baxendale

  DOI：10.1021/acs.joc.0c00656

  日期：2020.6.5

  A novel rearrangement sequence of 3-hydroxyazetidines via a Ritter initiated cascade provides highly substituted 2-oxazolines in high yields. The reaction conditions and substrate scope of the transformation have been studied demonstrating the generality of the process. The derived products can also be functionalized in order to undergo further intramolecular cyclization leading to a new class of macrocycle

  通过Ritter引发的级联反应的3-羟基氮杂环丁烷的新颖重排序列以高产率提供了高度取代的2-恶唑啉。研究了转化的反应条件和底物范围，证明了该方法的一般性。衍生的产物也可以被官能化，以进行进一步的分子内环化，从而产生一类新的大环。最终的环化步骤显示为适合连续流处理的转化，可显着减少反应时间并简单地按比例放大。
• Palladium-Catalyzed Synthesis of 3-Acylated Indoles Involving Oxidative Cross-Coupling of Indoles with α-Amino Carbonyl Compounds
  作者：Ri-Yuan Tang、Xiao-Kang Guo、Jian-Nan Xiang、Jin-Heng Li

  DOI：10.1021/jo402215s

  日期：2013.11.15

  selective C–N bond oxidative cleavage method to 3-acylated indoles by Pd-catalyzed oxidative cross coupling of indoles with α-amino carbonyl compounds has been developed; moreover, one-pot synthesis of 3-acylated indoles from 2-ethynylanilines and α-amino carbonyl compounds has also been established. Importantly, the products 3-acylated indoles can be used to construct polyheterocyclic compound, which can

  通过钯催化的吲哚与α-氨基羰基化合物的氧化交叉偶联，对3-酰化的吲哚进行了新的选择性的C-N键氧化裂解方法。此外，还建立了由2-乙炔基苯胺和α-氨基羰基化合物一锅合成3-酰化吲哚的方法。重要的是，产物3-酰化的吲哚可用于构建多杂环化合物，其可用作Hg 2+和Fe 3+的有效探针。
• Copper-Catalyzed Oxidative Self-Coupling of α-Amino Carbonyl Compounds for the Synthesis of Tetrasubstituted 1,4-Enediones
  作者：Bing Yi、Jiannan Xiang、Niannian Yi、Yi Xiong、Qingjun Huang、Ning Yan、Yanjun Xie、Donghui Lan、Ziqi Yi、Chak-Tong Au

  DOI：10.1055/s-0037-1611227

  日期：2018.11

  A protocol for the copper-catalyzed oxidative self-coupling of α-amino carbonyl compounds has been developed for the synthesis of tetrasubstituted 1,4-enediones (Z-isomers) in moderate to good yields through the cleavage of four sp3C–H bonds and the simultaneous formation of one C=C double bond in the α-amino carbonyl compound. The strategy has the advantages of using readily available starting ­materials

  铜催化氧化自偶联 α-氨基羰基化合物的方案已被开发用于合成四取代的 1,4-烯二酮（Z-异构体），通过四个 sp3C-H 键的裂解，以中等至良好的产率合成四取代的 1,4-烯二酮（Z-异构体）和在α-氨基羰基化合物中同时形成一个C=C双键。该策略具有使用容易获得的起始材料和高立体选择性的优点。
• Cu(OAc)2 and acids promoted the oxidative cleavage of α-aminocarbonyl compounds with amines: efficient and selective synthesis of 2-t-amino-2-imino-carbonyl and 2-amino-2-oxocarbonyl
  作者：De Chen、Chaozhihui Cheng、Sheng Zeng、Yongyue Luo、Jiajia Zhang、Wei Deng、Zebing Zeng、Ruijia Wang、Jiannan Xiang

  DOI：10.1016/j.tetlet.2020.151913

  日期：2020.5

  method for the synthesis of 2-t-amino-2-imino-carbonyl (C) and 2-amino-2-oxocarbonyl (D) compounds has been discovered through a copper-promoted oxidating amidation reactions between α-amino -carbonyl compounds and amines. Promoted by the crucial copper species, perfect selectivity and good to excellent yields could be achieved. This transformation is achieved through CN bond oxidative cleavage and formation

  通过α-氨基之间的铜促进的氧化酰胺化反应，发现了一种新颖且有效的合成2-叔氨基-2-亚氨基羰基（C）和2-氨基-2-氧羰基（D）化合物的方法。 -羰基化合物和胺。在关键的铜物种的促进下，可以实现完美的选择性和良好至极好的收率。这种转变是通过C N键的氧化裂解并形成新的C N键实现的。该反应体系具有广阔的反应范围，为α-氨基酮的α-官能化提供了简便的途径。
• Thiocyanation of α-amino carbonyl compounds for the synthesis of aromatic thiocyanates
  作者：Niannian Yi、Mingjing Ouyang、Huimin Liu、Miao Yan、Xiaoyong Wen、Yi Xiong、Bing Yi

  DOI：10.1177/1747519820923553

  日期：2021.1

  A procedure for K2S2O8-mediated thiocyanation of α-amino carbonyl compounds has been developed for the synthesis of aromatic thiocyanates. A series of α-amino carbonyl compounds have been investiga...

  已经开发了一种由 K2S2O8 介导的 α-氨基羰基化合物硫氰化的程序，用于合成芳香族硫氰酸酯。一系列α-氨基羰基化合物已被研究...