6-hydroxy-2-spirocyclohexyl-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: 6-hydroxy-2-spirocyclohexyl-2H-chromene
• 英文别名: Spiro[chromene-2,1'-cyclohexane]-6-ol
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: CUACBDBLJPNWNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-碘苯酚 在 Lindlar's catalyst 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1,1,3-三甲基-3-苯基二氢化茚-4,5-二甲酸 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 56.75h， 生成 6-hydroxy-2-spirocyclohexyl-2H-chromene
  参考文献：
  名称：

  The synthesis of 8a-methoxy-2H,6H-chromen-6-ones and corresponding 2H-chromenes by a unique process utilising phenolic oxidation

  摘要：

  (Z)-1-Hydroxy-3-(3'-hydroxyphenyl)prop-2-enes undergo phenolic oxidation by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2H,6H-dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substituted-Delta(3,4)-chromenes, the overall process being a unique heterocyclic synthesis in which the heteroatom is not initially attached to a benzene ring, but is introduced from a side chain. Parallel oxidations using cis-1-hydroxy-3-(3'-hydroxyphenyl)prop-2,3-oxiranes have also been achieved despite the presence of the sensitive oxirane ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00008-2

文献信息

• The synthesis of 8a-methoxy-2H,6H-chromen-6-ones and corresponding 2H-chromenes by a unique process utilising phenolic oxidation
  作者：Andrew Pelter、Amjad Hussain、Gareth Smith、Robert S Ward

  DOI：10.1016/s0040-4020(97)00008-2

  日期：1997.3

  (Z)-1-Hydroxy-3-(3'-hydroxyphenyl)prop-2-enes undergo phenolic oxidation by phenyliodonium diacetate (PIDA) in methanol to give 8a-methoxy-2H,6H-dihydrochromen-6-ones. These are reduced by DIBAL-H to 2-substituted-Delta(3,4)-chromenes, the overall process being a unique heterocyclic synthesis in which the heteroatom is not initially attached to a benzene ring, but is introduced from a side chain. Parallel oxidations using cis-1-hydroxy-3-(3'-hydroxyphenyl)prop-2,3-oxiranes have also been achieved despite the presence of the sensitive oxirane ring. (C) 1997 Elsevier Science Ltd.