(2α,5β,6α)-3,4,5,6-Tetrahydro-2-methyl-5-(1-methylethyl)-2,6-methano-2H-1-benzoxocin

• 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: (2α,5β,6α)-3,4,5,6-Tetrahydro-2-methyl-5-(1-methylethyl)-2,6-methano-2H-1-benzoxocin
• 英文别名: (1R,9R,12S)-9-methyl-12-propan-2-yl-8-oxatricyclo[7.3.1.02,7]trideca-2,4,6-triene
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: MXSJIXHZWFXKNE-JGGQBBKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  beta-pinene 、 苯酚 在 氢化铝 作用下， 反应 12.0h， 生成 (2α,5β,6α)-3,4,5,6-Tetrahydro-5-methyl-2-(1-methylethyl)-2,6-methano-2H-1-benzoxocin 、 (2α,5β,6α)-3,4,5,6-Tetrahydro-2-methyl-5-(1-methylethyl)-2,6-methano-2H-1-benzoxocin
  参考文献：
  名称：

  Aluminum phenoxide-promoted alkylation of phenol with α- and β-pinenes

  摘要：

  在 Al(OPh)3 存在下，苯酚与天然 α-和 β-蒎烯进行烷基化，得到具有结构不同萜烯片段的 O-和 C-烷基化产物。所获得的萜酚已被证明具有光学活性。

  DOI：

  10.1007/s11172-013-0062-9

文献信息

• Alkylation of aluminum phenolate with unsaturated monoterpenes
  作者：A. V. Kutchin、I. Yu. Chukicheva、I. V. Fedorova、O. A. Shumova

  DOI：10.1134/s0012500811040124

  日期：2011.4
• Products from the Acid-Catalyzed Reaction of Cyclic Monoterpenes and Phenol
  作者：John C. Schmidhauser、Garold L. Bryant、Paul E. Donahue、Mary F. Garbauskas、Elizabeth A. Williams

  DOI：10.1021/jo00117a009

  日期：1995.6

  Nine phenol-containing products from the acid-catalyzed reaction of phenol and gamma-terpinene were isolated and identified. A combination of X-ray crystallographic and spectroscopic techniques was used to assign the structures of the three p,p-bisphenols, two og-bisphenols, two bicyclic monophenols, and two bicyclic phenyl ethers. Several of the individual reaction products interconverted under acid-catalyzed conditions. The same nine products were formed using 3-carene, alpha-pinene, Limonene, or sabinene in place of gamma-terpinene, although the relative concentrations of these products varied depending upon the starting monoterpene's structure. A mechanism is proposed which accounts for the products' structures and reactivities.
• Aluminum phenoxide-promoted alkylation of phenol with α- and β-pinenes
  作者：A. V. Kutchin、O. A. Shumova、I. Yu. Chukicheva

  DOI：10.1007/s11172-013-0062-9

  日期：2013.2

  Alkylation of phenol with natural α- and β-pinenes in the presence of Al(OPh)3 gives the O- and C-alkylation products with the structurally different terpene fragments. The terpenophenols obtained have proved to be optically active.

  在 Al(OPh)3 存在下，苯酚与天然 α-和 β-蒎烯进行烷基化，得到具有结构不同萜烯片段的 O-和 C-烷基化产物。所获得的萜酚已被证明具有光学活性。