N-benzyl-N-methyl-2-(phenylethynyl)benzamide | 1551274-25-9

• 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-benzyl-N-methyl-2-(phenylethynyl)benzamide
• CAS: 1551274-25-9
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: CXUAPQUWEAKUOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-methyl-2-(phenylethynyl)benzamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以93%的产率得到N-benzyl-N-methyl-2-(phenylethynyl)benzothioamide
  参考文献：
  名称：

  Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine

  摘要：

  Reaction of o-alkynylbenzothioamide with molecular iodine was investigated. Unique benzo[c]thiophen-1-aminium iodide was obtained when the tertiary thioamide was used as a reactant. The reaction proceeded efficiently in less polar solvent, whereas the corresponding product was also obtained in a polar solvent. Single crystal X-ray analysis revealed that the benzo[c]thiophen-1-aminium structure possesses a resonance structure in N-C-S bond. Its stabilization shows a clear difference in the result from the reaction of amide analogue with iodine to give no stable compound. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.094
• 作为产物：
  描述：

  2-碘-N-甲基苯甲酰胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 121.0h， 生成 N-benzyl-N-methyl-2-(phenylethynyl)benzamide
  参考文献：
  名称：

  Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine

  摘要：

  Reaction of o-alkynylbenzothioamide with molecular iodine was investigated. Unique benzo[c]thiophen-1-aminium iodide was obtained when the tertiary thioamide was used as a reactant. The reaction proceeded efficiently in less polar solvent, whereas the corresponding product was also obtained in a polar solvent. Single crystal X-ray analysis revealed that the benzo[c]thiophen-1-aminium structure possesses a resonance structure in N-C-S bond. Its stabilization shows a clear difference in the result from the reaction of amide analogue with iodine to give no stable compound. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.094

文献信息

• Electrochemical synthesis of isobenzofuran-1-imines using oxidative halocyclization of <i>o</i>-alkynylbenzamides
  作者：Mandapati Bhargava Reddy、Rajagopal Peri、Muthuraaman Bhagavathiachari、Ramasamy Anandhan

  DOI：10.1039/d1ob00953b

  日期：——

  Electrochemical oxidative 5-exo-dig-oxo-halocyclization of o-alkynylbenzamides was achieved using readily available NaX (X = Cl, Br and I) salts under mild reaction conditions. The use of a cheap and highly stable sodium halide as a halide ion source is impressive for the synthesis of a variety of halogenated isobenzofuran-1-imines. This electrochemical protocol shows regioselectivity and excellent

  在温和的反应条件下，使用容易获得的 NaX（X = Cl、Br 和 I）盐实现了o-炔基苯甲酰胺的电化学氧化 5 -exo-dig -oxo-halocyclization 。使用廉价且高度稳定的卤化钠作为卤化物离子源对于合成各种卤代异苯并呋喃-1-亚胺是令人印象深刻的。该电化学方案在不使用化学计量的氧化剂和过渡金属催化剂的情况下以良好的收率显示出区域选择性和向异苯并呋喃-1-亚胺的出色转化。