2-(3-phenyl-propyl)-benzaldehyde | 101168-74-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(3-phenyl-propyl)-benzaldehyde
• 英文别名: 2-(3-Phenyl-propyl)-benzaldehyd
• CAS: 101168-74-5
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: GWQSWJRSVYUYGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-(3-phenyl-propyl)-benzoic acid anilide 在 五氯化磷 作用下， 生成 2-(3-phenyl-propyl)-benzaldehyde
  参考文献：
  名称：

  Experiments in the Colchicine Field. V. The Thermal and Photochemical Decomposition of Various 2-(β-Phenylethyl)-phenyldiazomethanes and 2-(γ-Phenylpropyl)-phenyldiazomethanes¹

  摘要：

  DOI：

  10.1021/ja01554a043

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.