N-(2-pent-1-ynylphenyl)butanamide | 366004-54-8

• 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-(2-pent-1-ynylphenyl)butanamide
• CAS: 366004-54-8
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: PVTCXRWZHIGEKY-UHFFFAOYSA-N

物化性质

• 沸点：
  405.3±28.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-pent-1-ynylphenyl)butanamide 在 N-甲基吡咯烷酮 、 potassium tert-butylate 作用下， 反应 6.0h， 以86%的产率得到2-丙基-1H-吲哚
  参考文献：
  名称：

  Chemistry of aminophenols. Part 1: Remarkable additive effect on Sonogashira cross-coupling of 2-carboxamidoaryl triflates and application to novel synthesis of indoles

  摘要：

  A novel and general synthesis of indoles has been established by utilizing 2-aminophenols as the starting materials. The key step is a modified Pd(0)-Cu(I)-catalyzed cross-coupling of 1-alkynes with 2-carboxamidoaryl triflates in the presence of n-Bu4NI as the additive. The 2-alkynylanilides obtained were subjected to an alkoxide-mediated cyclization to provide a number of indole containing compounds possessing substituents at the C2, C4, C5, and/or C6 position(s) in good overall yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00965-0
• 作为产物：
  描述：

  N-(2-hydroxyphenyl)butanamide 在 四(三苯基膦)钯 copper(l) iodide 、 四丁基碘化铵 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 N-(2-pent-1-ynylphenyl)butanamide
  参考文献：
  名称：

  Chemistry of aminophenols. Part 1: Remarkable additive effect on Sonogashira cross-coupling of 2-carboxamidoaryl triflates and application to novel synthesis of indoles

  摘要：

  A novel and general synthesis of indoles has been established by utilizing 2-aminophenols as the starting materials. The key step is a modified Pd(0)-Cu(I)-catalyzed cross-coupling of 1-alkynes with 2-carboxamidoaryl triflates in the presence of n-Bu4NI as the additive. The 2-alkynylanilides obtained were subjected to an alkoxide-mediated cyclization to provide a number of indole containing compounds possessing substituents at the C2, C4, C5, and/or C6 position(s) in good overall yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00965-0

文献信息

• Amide Oxygen-Assisted Palladium-Catalyzed Hydration of Alkynes
  作者：Zhenming Zhang、Lihuan Wu、Jianhua Liao、Wanqing Wu、Huanfeng Jiang、Jianxiao Li、Jiawei Li

  DOI：10.1021/acs.joc.5b01178

  日期：2015.8.7

  oxygen-assisted palladium-catalyzed hydration reaction of alkynes is realized to prepare a series of o-acylacetanilide derivatives with high yield, and single regioselectivity under mild reaction conditions. This transformation is simple, practical, and can be performed on a gram scale. Evaluation of the mechanism shows that the reaction should involve an oxypalladation process, and the 1,3-oxazine compound

  在此，实现了炔烃的酰胺氧辅助钯催化的水合反应，以高收率，在温和的反应条件下具有单区域选择性的方式制备了一系列邻酰基乙酰苯胺衍生物。此转换简单，实用，并且可以以克为单位执行。对该机理的评估表明，该反应应包括羰基缩合过程，并且已证明1,3-恶嗪化合物是关键中间体。