1,2-Ethandiylbis(3-benzaldehyd) | 142421-25-8

• 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: 1,2-Ethandiylbis(3-benzaldehyd)
• 英文别名: 3-[2-(3-formylphenyl)ethyl]benzaldehyde
• CAS: 142421-25-8
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: WRKNQIXVKLZCQI-UHFFFAOYSA-N

物化性质

• 沸点：
  383.0±35.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,2-Ethandiylbis(3-benzaldehyd) 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以93%的产率得到3,3'-bis(hydroxymethyl)diphenylethane
  参考文献：
  名称：

  Bauer, Martin; Nieger, Martin; Voegtle, Fritz, Chemische Berichte, 1992, vol. 125, # 11, p. 2533 - 2538

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶-1-甲醛 、 3,3'-Dibrom-bibenzyl 在 正丁基锂 作用下， 生成 1,2-Ethandiylbis(3-benzaldehyd)
  参考文献：
  名称：

  Bauer, Martin; Nieger, Martin; Voegtle, Fritz, Chemische Berichte, 1992, vol. 125, # 11, p. 2533 - 2538

  摘要：

  DOI：

文献信息

• Influence of Conformation and Proton-Transfer Dynamics in the Dibenzyl σ-Complex on Regioselectivity in Gattermann−Koch Formylation via Intracomplex Reaction
  作者：Mutsuo Tanaka、Masahiro Fujiwara、Qiang Xu、Hisanori Ando、Todd J. Raeker

  DOI：10.1021/jo980228t

  日期：1998.6.1

  The Gattermann-Koch formylations of diphenyl, diphenylmethane, dibenzyl, and 1,3-diphenylpropane were studied in HF-SbFS5, -TaF5, -BF3, -NbF5, and CF3SO3H-SbF5. While usual high para regioselectivity was obtained for diphenyl, diphenylmethane, and 1,3-diphenylpropane, unprecedented ortho regioselectivity was observed for dibenzyl which increased with decreasing the SbF5/dibenzyl molar ratio and with strength of Lewis acids used in KF. A sandwich-like complex for monoprotonated dibenzyl resulting in ortho regioselectivity via the intracomplex reaction was suggested; therefore, the conformations of protonated diphenylmethane, dibenzyl, and 1,3-diphenylpropane and their proton-transfer dynamics were probed by semiempirical calculation (PM3). The calculation predicted that ortho monoprotonation was slightly preferable for dibenzyl, and remarkable preference of dibenzyl over other aromatic compounds was observed in ortho-ortho intramolecular inter-ring proton transfer via a fan-shaped complex rather than a sandwich-like complex. The experimental and theoretical data for dibenzyl are compatible with the intracomplex reaction, whereby CO is protonated by the ortho sigma-complex undergoing rapid interring proton transfer to generate formyl cation in the vicinity of the ortho position leading to ortho regioselectivity.
• Bauer, Martin; Nieger, Martin; Voegtle, Fritz, Chemische Berichte, 1992, vol. 125, # 11, p. 2533 - 2538
  作者：Bauer, Martin、Nieger, Martin、Voegtle, Fritz

  DOI：——

  日期：——