trans-2-<2-(N,-methylamino)ethyl>stilbene | 161521-67-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-2-<2-(N,-methylamino)ethyl>stilbene
• 英文别名: (E)-N-methyl-2-(2-styrylphenyl)ethanamine；N-methyl-2-[2-[(E)-2-phenylethenyl]phenyl]ethanamine
• CAS: 161521-67-1
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: WBEKMWVNZXDQAK-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  trans-2-<2-(N,-methylamino)ethyl>stilbene 在 1-叔丁基-4,4,4-三(二甲氨基)-2,2-二[三(二甲氨基)-正膦亚基氨基]-2Λ5,4Λ5-连二(磷氮基化合物) 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以68%的产率得到1-苄基-2-甲基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  磷腈碱催化氨基烯烃加氢胺化构建异二氢吲哚支架：在马兜铃碱全合成中的应用

  摘要：

  建立了磷腈碱催化氨基烯烃分子内加氢胺化合成异二氢吲哚的方法。该反应具有广泛的官能团耐受性，包括卤化物、氰基和甲氧基，也可用于合成四氢异喹啉、吡咯烷和哌啶。该方法被用作马兜铃碱全合成的关键步骤，分六步进行，总产率为 35%。该策略涉及通过控制所需 C N 键的形成来构建异二氢吲哚核心，而相对不稳定的甲氧基甲基和芳基溴保持完整。

  DOI：

  10.1016/j.tetlet.2021.153599
• 作为产物：
  描述：

  (E)-N-methyl-2-(2-styrylphenyl)acetamide 在 lithium aluminium tetrahydride 作用下， 生成 trans-2-<2-(N,-methylamino)ethyl>stilbene
  参考文献：
  名称：

  Photophysics and Photochemistry of Intramolecular Stilbene-Amine Exciplexes

  摘要：

  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.

  DOI：

  10.1021/ja00107a010

文献信息

• Catalytic asymmetric intramolecular hydroamination of aminoalkenes
  作者：Tokutaro Ogata、Atsushi Ujihara、Susumu Tsuchida、Tomoko Shimizu、Atsunori Kaneshige、Kiyoshi Tomioka

  DOI：10.1016/j.tetlet.2007.07.117

  日期：2007.9

  Asymmetric intramolecular cyclization of aminoalkenes was catalyzed by a catalytic amount of n-butyllithium, diisopropylamine, and a newly designed chiral bisoxazoline in toluene to produce kinetically controlled exo-cyclized amines with up to 91% ee quantitatively. (c) 2007 Elsevier Ltd. All rights reserved.
• Phosphazene base-catalyzed hydroamination of aminoalkenes for the construction of isoindoline scaffolds: Application to the total synthesis of aristocularine
  作者：Junpei Matsuoka、Maki Terashita、Akari Miyawaki、Kiyoshi Tomioka、Yasutomo Yamamoto

  DOI：10.1016/j.tetlet.2021.153599

  日期：2022.1

  A method for isoindoline synthesis via phosphazene base-catalyzed intramolecular hydroamination of aminoalkenes was developed. The reaction has a broad functional group tolerance, including for halide, cyano, and methoxy groups, and could also be used to synthesize tetrahydroisoquinoline, pyrrolidine, and piperidine. The method was used as a key step in the total synthesis of aristocularine in six

  建立了磷腈碱催化氨基烯烃分子内加氢胺化合成异二氢吲哚的方法。该反应具有广泛的官能团耐受性，包括卤化物、氰基和甲氧基，也可用于合成四氢异喹啉、吡咯烷和哌啶。该方法被用作马兜铃碱全合成的关键步骤，分六步进行，总产率为 35%。该策略涉及通过控制所需 C N 键的形成来构建异二氢吲哚核心，而相对不稳定的甲氧基甲基和芳基溴保持完整。
• 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.