1-benzyltetrahydro-2-benzazepine | 61034-51-3

• 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-benzyltetrahydro-2-benzazepine
• 英文别名: 1-benzyl-2,3,4,5-tetrahydro-1H-2-benzazepine
• CAS: 61034-51-3
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: LEUSREVDHIFBSC-UHFFFAOYSA-N

物化性质

• 沸点：
  371.8±11.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyltetrahydro-2-benzazepine 、 1-萘甲酰氯 在 TEA 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)1-benzyl-2,3,4,5-tetrahydro-1H-2-benzazepine naphthamide
  参考文献：
  名称：

  The asymmetric synthesis of 1-alkyl-2,3,4,5-tetrahydro-benzazepines and benzo[β]-1-azabicyclo[5,3,1]decanes

  摘要：

  The metalation-alkylation of benzazepine formamidines gives high yields and good diastereoselectivity of 1-substituted derivatives. Removal of the chiral auxiliary leads to the title compounds in 84-96% ee and represents the first chiral benzazepines prepared via asymmetric synthesis.

  DOI：

  10.1016/s0040-4020(01)80537-8
• 作为产物：
  描述：

  3-(2-溴苯基)丙烷-1-胺 在 palladium diacetate 、 lithium aluminium tetrahydride 、 正丁基锂 、 一水合肼 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 xylene 为溶剂， 反应 24.5h， 生成 1-benzyltetrahydro-2-benzazepine
  参考文献：
  名称：

  The asymmetric synthesis of 1-alkyl-2,3,4,5-tetrahydro-benzazepines and benzo[β]-1-azabicyclo[5,3,1]decanes

  摘要：

  The metalation-alkylation of benzazepine formamidines gives high yields and good diastereoselectivity of 1-substituted derivatives. Removal of the chiral auxiliary leads to the title compounds in 84-96% ee and represents the first chiral benzazepines prepared via asymmetric synthesis.

  DOI：

  10.1016/s0040-4020(01)80537-8

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.