1-benzoyl-5-methylidene-2,3,4,5-tetrahydro-1H-benzazepine | 848172-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-benzoyl-5-methylidene-2,3,4,5-tetrahydro-1H-benzazepine
• 英文别名: (5-methylidene-3,4-dihydro-2H-1-benzazepin-1-yl)-phenylmethanone
• CAS: 848172-01-0
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: RGSUJHTVWCFTAD-UHFFFAOYSA-N

物化性质

• 沸点：
  419.2±28.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  1-benzoyl-5-methylidene-2,3,4,5-tetrahydro-1H-benzazepine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以86%的产率得到1-benzoyl-5-methyl-2,3,4,5-tetrahydro-1H-1-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：

  5-(p-toluenesulphonyl)-1-pentene 在 palladium diacetate 、 sodium hydride 、 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 20.0h， 生成 1-benzoyl-5-methylidene-2,3,4,5-tetrahydro-1H-benzazepine
  参考文献：
  名称：

  N-苯甲酰基-5-取代-1-苯并ze庚因的立体化学：构象偏倚的衍生物的合成和报告结构的修订。

  摘要：

  的顺式（一- [R *，5 R *）和反（一个小号*，5 R *）非对映体ñ -苯甲酰-C5取代的-1-苯并吖庚因源于在C5和上述Ar-N的手性（C = O首先通过分别用C6和C9处的取代基偏向构象来立体选择性地合成α）轴。通过X射线晶体学分析，VT NMR和DFT计算，对这些N-苯甲酰基-1-苯并ze庚因的立体化学（即构象和构型）进行了详细检查，揭示了这些杂环的新物理化学方面，包括先前报道的立体化学的修订。

  DOI：

  10.1021/acs.joc.5b02900

文献信息

• Stereochemistry of<i>N</i>-Benzoyl-5-substituted-1-benzazepines Revisited: Synthesis of the Conformationally Biased Derivatives and Revision of the Reported Structure
  作者：Hidetsugu Tabata、Tetsuya Yoneda、Tomohiko Tasaka、Shigekazu Ito、Tetsuta Oshitari、Hideyo Takahashi、Hideaki Natsugari

  DOI：10.1021/acs.joc.5b02900

  日期：2016.4.15

  with a substituent at C6 and C9, respectively. Detailed examination of the stereochemistry (i.e., conformation and configuration) of these N-benzoyl-1-benzazepines by X-ray crystallographic analysis, VT NMR, and DFT calculations revealed new physicochemical aspects of these heterocycles including revision of the stereochemistry previously reported.

  的顺式（一- [R *，5 R *）和反（一个小号*，5 R *）非对映体ñ -苯甲酰-C5取代的-1-苯并吖庚因源于在C5和上述Ar-N的手性（C = O首先通过分别用C6和C9处的取代基偏向构象来立体选择性地合成α）轴。通过X射线晶体学分析，VT NMR和DFT计算，对这些N-苯甲酰基-1-苯并ze庚因的立体化学（即构象和构型）进行了详细检查，揭示了这些杂环的新物理化学方面，包括先前报道的立体化学的修订。
• Conformation Analyses, Dynamic Behavior and Amide Bond Distortions of Medium-sized Heterocycles. 1. Partially and Fully Reduced 1-Benzazepines
  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/jo048118b

  日期：2005.3.1

  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.