rac-cis-6-methyl-4-(naphthalen-2-yl)-2-phenyl-3,6-dihydro-2H-pyran

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: rac-cis-6-methyl-4-(naphthalen-2-yl)-2-phenyl-3,6-dihydro-2H-pyran
• 英文别名: (2S,6S)-6-methyl-4-naphthalen-2-yl-2-phenyl-3,6-dihydro-2H-pyran
• 化学式: C₂₂H₂₀O
• 分子量: 300.4
• InChiKey: BCLHSKQFVMVZOY-AOMKIAJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-2-(2-naphthyl)-1,3-pentadiene 、 苯甲醛 在 [Fe(5,10,15,20-tetraphenylporphyrin)]BF₄ 作用下， 以 苯 为溶剂， 反应 12.0h， 以88%的产率得到rac-cis-6-methyl-4-(naphthalen-2-yl)-2-phenyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Cationic Iron(III) Porphyrin-Catalyzed [4 + 2] Cycloaddition of Unactivated Aldehydes with Simple Dienes

  摘要：

  Cationic iron(III) porphyrin was found to be an efficient catalyst for the highly chemoselective hetero-Diels Alder-type reaction of aldehydes with 1,3-dienes. The catalyzed process did not require the use of electron-deficient aldehydes such as glyoxylic acid derivatives or activated electron-rich 1,3-dienes such as Danishefslcy's diene and Rawal's diene. The high functional group tolerance and robustness of the catalyst were demonstrated. Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene.

  DOI：

  10.1021/ja300790x

文献信息

• Cationic Iron(III) Porphyrin-Catalyzed [4 + 2] Cycloaddition of Unactivated Aldehydes with Simple Dienes
  作者：Kyohei Fujiwara、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ja300790x

  日期：2012.3.28

  Cationic iron(III) porphyrin was found to be an efficient catalyst for the highly chemoselective hetero-Diels Alder-type reaction of aldehydes with 1,3-dienes. The catalyzed process did not require the use of electron-deficient aldehydes such as glyoxylic acid derivatives or activated electron-rich 1,3-dienes such as Danishefslcy's diene and Rawal's diene. The high functional group tolerance and robustness of the catalyst were demonstrated. Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene.