N-(2-iodophenyl)-N-(pent-4-en-1-yl)benzamide | 848171-99-3

• 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-iodophenyl)-N-(pent-4-en-1-yl)benzamide
• 英文别名: N-(2-iodophenyl)-N-pent-4-enylbenzamide
• CAS: 848171-99-3
• 化学式: C₁₈H₁₈INO
• 分子量: 391.252
• InChiKey: LXCYRRJMKSBUIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-iodophenyl)-N-(pent-4-en-1-yl)benzamide 在 palladium diacetate 三乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以88%的产率得到1-benzoyl-5-methylidene-2,3,4,5-tetrahydro-1H-benzazepine
  参考文献：
  名称：

  Conformation Analyses, Dynamic Behavior and Amide Bond Distortions of Medium-sized Heterocycles. 1. Partially and Fully Reduced 1-Benzazepines

  摘要：

  Five 1-benzazepine heterocycles were synthesized by utilizing transition-metal-catalyzed processes in key bond-forming steps. exo-Methylene and methyl substituents were introduced at position 5, as well as a unit of unsaturation between positions 3 and 4, with benzoyl or benzyl N-substituents. Solution- and solid-state structures were examined, using dynamic NMR spectroscopy and X-ray crystallography, corroborated by molecular mechanics calculations. Greater amide distortion is associated with a more stable ground-state structure, which is in turn more reluctant to undergo conformational changes.

  DOI：

  10.1021/jo048118b
• 作为产物：
  描述：

  toluene-4-sulfonic acid pent-4-enyl ester 、 o-iodobenzanilide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以83%的产率得到N-(2-iodophenyl)-N-(pent-4-en-1-yl)benzamide
  参考文献：
  名称：

  Conformation Analyses, Dynamic Behavior and Amide Bond Distortions of Medium-sized Heterocycles. 1. Partially and Fully Reduced 1-Benzazepines

  摘要：

  Five 1-benzazepine heterocycles were synthesized by utilizing transition-metal-catalyzed processes in key bond-forming steps. exo-Methylene and methyl substituents were introduced at position 5, as well as a unit of unsaturation between positions 3 and 4, with benzoyl or benzyl N-substituents. Solution- and solid-state structures were examined, using dynamic NMR spectroscopy and X-ray crystallography, corroborated by molecular mechanics calculations. Greater amide distortion is associated with a more stable ground-state structure, which is in turn more reluctant to undergo conformational changes.

  DOI：

  10.1021/jo048118b

文献信息

• Conformation Analyses, Dynamic Behavior, and Amide Bond Distortions of Medium-sized Heterocycles. 2. Partially and Fully Reduced 1-Benzazocines, Benzazonines, and Benzazecines
  作者：Maryiam Qadir、Jonathan Cobb、Peter W. Sheldrake、Neil Whittall、Andrew J. P. White、King Kuok (Mimi) Hii、Peter N. Horton、Michael B. Hursthouse

  DOI：10.1021/jo048117j

  日期：2005.3.1

  forms of benzo-fused eight- to ten-membered nitrogen heterocycles (1-benzazecines, 1-benzazonines and 1-benzazecines) have been prepared. Conformational features, transannular distances and dynamic behavior were studied using X-ray crystallography and VT NMR spectroscopy. The amide moiety in the nine-membered benzazonine ring 5b favors N-pyramidization, whereas the ten-membered benzazecine 5c adopts

  已经制备了部分和完全还原形式的苯并稠合的八元至十元氮杂环（1-苯并ze嗪，1-苯并zon嗪和1-苯并ze嗪）。使用X射线晶体学和VT NMR光谱研究了构象特征，跨环距离和动力学行为。九元苯并zon嗪环5b中的酰胺部分有利于N-金字塔化，而十元苯并ze嗪5c采用酰胺捻。分子力学计算揭示了酰胺捻度（τ）与环稳定性之间的相关性。还发现溶液中杂环的动力学行为取决于酰胺变形的程度和性质。因此，我们得出结论，这些中等大小的杂环的环应变通过酰胺变形得以缓解，这导致了更稳定的结构。