2,3,4,5-tetrahydro-2-phenyl-3-methyl-1H-3-benzazepine | 46889-78-5

• 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: 2,3,4,5-tetrahydro-2-phenyl-3-methyl-1H-3-benzazepine
• 英文别名: N-methyl-2-phenyltetrahydro-3-benzazepine；3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine；2-Phenyl-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin；3-Methyl-4-phenyl-1,2,4,5-tetrahydro-3-benzazepine
• CAS: 46889-78-5
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: SZECIXINYMSONF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-methyl-3,4-dihydroisoquinolinium iodide 在 盐酸 、 sodium tetrahydroborate 、 cesium fluoride 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 2.5h， 生成 2,3,4,5-tetrahydro-2-phenyl-3-methyl-1H-3-benzazepine
  参考文献：
  名称：

  Fluoride ion promoted reactions of .alpha.-halo silanes: synthesis of stilbenes, epoxides, cyclopropanes, benzazepines, and phthalidylisoquinolines

  摘要：

  Reaction of alpha-halo silanes 1 with CsF in DMF affords stilbenes 5. In the presence of added aldehydes, epoxides 6 are obtained, while with electron-deficient olefins the corresponding cyclopropanes 7 are formed. A similar reaction of 1a with iminium compounds 8 in HMPA leads to 2-phenyl-3-benzazepines 12, whereas 1b or 17 furnishes phthalidylisoquinolines 15.

  DOI：

  10.1021/jo00012a024

文献信息

• Photochemical synthesis of tetrahydrobenzazepines via intramolecular stilbene-amine photoaddition
  作者：Frederick D. Lewis、G. Dasharatha Reddy

  DOI：10.1016/s0040-4039(00)74230-4

  日期：1992.7

  The photochemical reactions of several ortho-(aminoalkyl)stilbenes and their N-methyl derivatives have been investigated under conditions of direct and electron-transfer sensitized irradiation and are found to provide an efficient method for the synthesis of benzazepines.

  在直接和电子转移敏化辐射的条件下，已经研究了几种邻-（氨基烷基）对苯二甲酸酯和它们的N-甲基衍生物的光化学反应，发现它们为合成苯并ze庚因提供了一种有效的方法。
• Photophysics and Photochemistry of Intramolecular Stilbene-Amine Exciplexes
  作者：Frederick D. Lewis、Dario M. Bassani、Eric L. Burch、Bliss E. Cohen、Jeffrey A. Engleman、G. Dasharatha Reddy、Siegfried Schneider、Wighard Jaeger、Peter Gedeck、Michael Gahr

  DOI：10.1021/ja00107a010

  日期：1995.1

  The photophysical and photochemical behavior of a series of trans-(aminoalkyl)stilbenes in which a primary, secondary, or tertiary amine is appended to the stilbene ortho position with a methyl, ethyl, or propyl linker has been investigated. The tertiary (aminoalkyl)stilbenes form fluorescent exciplexes and undergo trans-cis isomerization, but fail to undergo intramolecular reactions analogous to intermolecular addition reactions observed for stilbene with tertiary amines. The photophysical behavior of the tertiary (aminoalkyl)stilbenes is dependent upon the choice of linker, solvent, and temperature. The secondary (aminoalkyl)stilbenes do not form fluorescent exciplexes but undergo intramolecular N-H addition to the stilbene double bond. Unlike the intermolecular reactions of substituted stilbenes with secondary amines, which yield mixtures of regioisomeric adducts and reduction products, the intramolecular reactions are highly selective, providing an efficient method for the synthesis of tetrahydrobenzazepines. Direct irradiation of the primary (aminoalkyl)stilbenes results only in trans-cis isomerization. However, irradiation in the presence of the electron acceptor p-dicyanobenzene results in regioselective intramolecular N-H addition to the stilbene double bond. These results are discussed in terms of the mechanisms of direct and electron-transfer-sensitized irradiation.
• Fluoride ion promoted reactions of .alpha.-halo silanes: synthesis of stilbenes, epoxides, cyclopropanes, benzazepines, and phthalidylisoquinolines
  作者：Satinder V. Kessar、Paramjit Singh、Nachhattar Pal Kaur、Usha Chawla、Kalpana Shukla、Punam Aggarwal、D. Venugopal

  DOI：10.1021/jo00012a024

  日期：1991.6

  Reaction of alpha-halo silanes 1 with CsF in DMF affords stilbenes 5. In the presence of added aldehydes, epoxides 6 are obtained, while with electron-deficient olefins the corresponding cyclopropanes 7 are formed. A similar reaction of 1a with iminium compounds 8 in HMPA leads to 2-phenyl-3-benzazepines 12, whereas 1b or 17 furnishes phthalidylisoquinolines 15.