trans-stilbene-4,4'-d2 | 90625-42-6

• 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-stilbene-4,4'-d2
• 英文别名: trans-4,4'-dideuterio-stilbene；(E)-1,2-diphenylethene-4,4'-d₂；trans-Stilben-4,4'-D2；4,4'-Dideutero-stilben-trans；trans-1,2-bis-(4-deuterio-phenyl)-ethene；t-Stilben-4,4'-d(2)；trans-4,4'-Dideuterostilbene；1-deuterio-4-[(E)-2-(4-deuteriophenyl)ethenyl]benzene
• CAS: 90625-42-6
• 化学式: C₁₄H₁₂
• 分子量: 182.233
• InChiKey: PJANXHGTPQOBST-RBDZDZJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-deuteriotoluene 在 溴 、 mercury dichloride 、 锌 作用下， 以 四氯化碳 、 乙醇 、 重水 为溶剂， 生成 trans-stilbene-4,4'-d2
  参考文献：
  名称：

  Unusual deuterium isotope effects in13C NMR spectra oftrans-stilbene

  摘要：

  AbstractA detailed analysis of the 13C NMR spectra of trans‐stilbene and ten deuteriated trans‐stilbenes has been undertaken. Some unusual deuterium isotope effects on carbon–hydrogen spin–spin coupling constants could not be explained by the ordinary primary and secondary isotope effects. The positive and negative changes of nJ(CH) were interpreted in terms of a steric effect, the vibrational influence of the CD bond and the para‐effect induced by deuterium. In this respect, deuterium behaves as a real substituent with electronic properties different from those of hydrogen. The deuterium isotope effects on 13C NMR chemical shifts and carbon–deuterium coupling constants have also been determined.

  DOI：

  10.1002/mrc.1270220409

文献信息

• Synthesis of <i>trans</i>-stilbenes <i>via</i> phosphine-catalyzed coupling reactions of benzylic halides
  作者：Sheng Zhang、Zhilong Xie、Zhanqiang Ye、Mingyang Zhang、Dongdeng Li、Masahiko Yamaguchi、Ming Bao

  DOI：10.1039/d2ob01237e

  日期：——

  are also generated from the reactions of benzyl chlorides with phosphonium salts. Several P-based key intermediates have been detected by NMR and HRMS analyses, which shed light on the postulated catalytic cycle. In the presence of different bases, the transformations involve two different pathways, in which phenylcarbene and phosphonium alkoxide are considered as key intermediates, respectively. The

  描述了一种高效实用的膦催化氯化苄的均偶联反应。在 CsF/B(OMe) 3和 NaH 作为碱的存在下，反应顺利进行，分别提供反式-二苯乙烯产量高，范围广。苄基氯与鏻盐的反应也产生不对称二苯乙烯。通过 NMR 和 HRMS 分析检测到几种 P 基关键中间体，这揭示了假定的催化循环。在不同碱基存在下，转化涉及两种不同的途径，其中苯卡宾和醇鏻分别被认为是关键中间体。这两种途径在合成上互补，但在机制上不同。合成效用，包括克级反应和直接获得 π 共轭分子，也已得到证明。
• Unusual deuterium isotope effects in13C NMR spectra oftrans-stilbene
  作者：Ziatko Meić、Dražen Vikić-topić、Hans Güsten

  DOI：10.1002/mrc.1270220409

  日期：1984.4

  AbstractA detailed analysis of the 13C NMR spectra of trans‐stilbene and ten deuteriated trans‐stilbenes has been undertaken. Some unusual deuterium isotope effects on carbon–hydrogen spin–spin coupling constants could not be explained by the ordinary primary and secondary isotope effects. The positive and negative changes of nJ(CH) were interpreted in terms of a steric effect, the vibrational influence of the CD bond and the para‐effect induced by deuterium. In this respect, deuterium behaves as a real substituent with electronic properties different from those of hydrogen. The deuterium isotope effects on 13C NMR chemical shifts and carbon–deuterium coupling constants have also been determined.