trans-2-(cyanomethyl)stilbene | 69277-24-3

• 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-(cyanomethyl)stilbene
• 英文别名: (E)-2-(2-styrylphenyl)acetonitrile；trans-stilbenyl-(2)-acetonitrile；2-[2-[(E)-2-phenylethenyl]phenyl]acetonitrile
• CAS: 69277-24-3
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: CPUXAFJADHYCNU-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trans-2-(cyanomethyl)stilbene 在 lithium aluminium tetrahydride 作用下， 以83%的产率得到trans-2-(2-aminoethyl)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
• 作为产物：
  描述：

  2-styryl-benzyl alcohol 在 氯化亚砜 、 乙醇 作用下， 生成 trans-2-(cyanomethyl)stilbene
  参考文献：
  名称：

  Synthesis of Derivatives of Diphenylethane Related to Materials Occurring Naturally. IV. Stilbene-2-acetic Acid

  摘要：

  DOI：

  10.1021/ja01264a066

文献信息

• Palladium-Catalyzed Tandem C(sp³)-H Insertion Cyclization of 2-(2-Vinylarene)acetonitriles with Isocyanides to Access Naphthalen-2-amines
  作者：Huishu Lin、Yongzhou Pan、Jinping Fu、Yi Yi、Haitao Tang、Yingming Pan、Wanguo Yu、Xu Wang

  DOI：10.1021/acs.joc.3c01142

  日期：2023.9.1