7-methyl-4-methylidene-2-phenyloctahydro-2H-chromene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-methyl-4-methylidene-2-phenyloctahydro-2H-chromene
• 英文别名: 7-methyl-4-methylidene-2-phenyl-2,3,4a,5,6,7,8,8a-octahydrochromene
• 化学式: C₁₇H₂₂O
• 分子量: 242.361
• InChiKey: GLFDCGKHCDCFLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  4,7-Dimethyl-2-phenyl-2,3,4a,5,6,7,8,8a-octahydrochromen-4-ol 在 ce-Beta-150 zeolite 作用下， 反应 2.0h， 生成 7-methyl-4-methylidene-2-phenyloctahydro-2H-chromene
  参考文献：
  名称：

  Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts

  摘要：

  Tetrahydropyrans, compounds with 6-membered oxygen-containing heterocycles, are widely used for the synthesis of biologically active compounds with analgesic, anti-inflammatory or cytotoxic activity. Synthesis of compounds with the desired structure can be realized by several methods, including the acidic catalyzed Prins cyclization of homoallylic alcohol with simple aldehydes. In the current study, synthesis of compounds with the desired tetrahydropyran framework by Prins cyclization of benzaldehyde and alcohols with different structure, namely isopulegol and 3-methyl-6-(prop-1-en-2-yl)cyclohex-3ene-1,2-diol, was investigated. Different parent zeolites as well as their metal modified forms and mesoporous materials were employed in the comparative investigation. Activity and selectivity of the tested catalysts were correlated with their physico-chemical properties. The highest conversion and selectivity toward the product with the tetrohydropyran structure was achieved using Ce-MCM-41 in the interactions of isopulegol and benzaldehyde. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2015.09.021

文献信息

• Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts
  作者：Martina Stekrova、Päivi Mäki-Arvela、Narendra Kumar、Erfan Behravesh、Atte Aho、Quentin Balme、Konstantin P. Volcho、Nariman F. Salakhutdinov、Dmitry Yu. Murzin

  DOI：10.1016/j.molcata.2015.09.021

  日期：2015.12

  Tetrahydropyrans, compounds with 6-membered oxygen-containing heterocycles, are widely used for the synthesis of biologically active compounds with analgesic, anti-inflammatory or cytotoxic activity. Synthesis of compounds with the desired structure can be realized by several methods, including the acidic catalyzed Prins cyclization of homoallylic alcohol with simple aldehydes. In the current study, synthesis of compounds with the desired tetrahydropyran framework by Prins cyclization of benzaldehyde and alcohols with different structure, namely isopulegol and 3-methyl-6-(prop-1-en-2-yl)cyclohex-3ene-1,2-diol, was investigated. Different parent zeolites as well as their metal modified forms and mesoporous materials were employed in the comparative investigation. Activity and selectivity of the tested catalysts were correlated with their physico-chemical properties. The highest conversion and selectivity toward the product with the tetrohydropyran structure was achieved using Ce-MCM-41 in the interactions of isopulegol and benzaldehyde. (C) 2015 Elsevier B.V. All rights reserved.