3-phenylcitronellal | 70645-63-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-phenylcitronellal
• 英文别名: 3,7-Dimethyl-3-phenyloct-6-enal
• CAS: 70645-63-5
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: QIDOEMYDILNWNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenylcitronellal 在 Al-MCM-41 作用下， 以 甲苯 为溶剂， 生成 5-methyl-5-phenyl-2-(prop-1-en-2-yl)cyclohexanol
  参考文献：
  名称：

  BINOL-Al catalyzed kinetic resolution of citronellal analogues: synthesis of a variety of fragrances

  摘要：

  A chiral aluminum catalyst was used for the kinetic resolution of citronellal analogues. Racemic 3-alkyl-citronellals gave optically active 5-alkylisopulegols with high enantioselectivity. Unreacted 3-alkyl-citronellal analogues were obtained with low enantioselectivity. The two main diastereoisomers of the product were opposite to each other. The scents of 5-substituted isopulegols were evaluated. The chiral recognition of the catalysts and their effects on the kinetic resolutions are also discussed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.007
• 作为产物：
  描述：

  溴苯 、 (E)-3,7-二甲基-2,6-辛二烯醛 以69%的产率得到
  参考文献：
  名称：

  SOUZA, BARBOZA, J. C. DE;PETRIER, CH.;LUCHE, J. -L., TETRAHEDRON LETT., 1985, 26, N 7, 829-830

  摘要：

  DOI：

文献信息

• Highly selective aluminium-catalysed intramolecular Prins reaction for <scp>l</scp>-menthol synthesis
  作者：H. Itoh、H. Maeda、S. Yamada、Y. Hori、T. Mino、Masami Sakamoto

  DOI：10.1039/c4ra12470g

  日期：——

  The perfect production of l-menthol.

  l-薄荷脑的完美生产。
• Correction: Highly selective aluminium-catalysed intramolecular Prins reaction for <scp>l</scp>-menthol synthesis
  作者：H. Itoh、H. Maeda、S. Yamada、Y. Hori、T. Mino、Masami Sakamoto

  DOI：10.1039/c5ra90068a

  日期：——

  Correction for ‘Highly selective aluminium-catalysed intramolecular Prins reaction for L-menthol synthesis’ by H. Itoh et al., RSC Adv., 2014, 4, 61619–61623.

  H. Itoh等人对“用于L-薄荷醇合成的高选择性铝催化的分子内Prins反应”的校正。，RSC Adv。，2014，4，61619-61623。
• Tietze, Lutz F.; Steinmetz, Adrian, Angewandte Chemie, 1996, vol. 108, # 6, p. 682 - 683
  作者：Tietze, Lutz F.、Steinmetz, Adrian

  DOI：——

  日期：——
• Sonochemically prepared organozinc reagents1. conjugate additions to α-β unsaturated aldehydes
  作者：Jayne Carlos de Souza Barboza、Christian Pétrier、Jean-Louis Luche

  DOI：10.1016/s0040-4039(00)61939-1

  日期：1985.1
• BINOL-Al catalyzed kinetic resolution of citronellal analogues: synthesis of a variety of fragrances
  作者：Hisanori Itoh、Hironori Maeda、Shinya Yamada、Yoji Hori、Takashi Mino、Masami Sakamoto

  DOI：10.1016/j.tetasy.2016.06.007

  日期：2016.8

  A chiral aluminum catalyst was used for the kinetic resolution of citronellal analogues. Racemic 3-alkyl-citronellals gave optically active 5-alkylisopulegols with high enantioselectivity. Unreacted 3-alkyl-citronellal analogues were obtained with low enantioselectivity. The two main diastereoisomers of the product were opposite to each other. The scents of 5-substituted isopulegols were evaluated. The chiral recognition of the catalysts and their effects on the kinetic resolutions are also discussed. (C) 2016 Elsevier Ltd. All rights reserved.