6-methyl-3-[2'-cyclohexenyl]-4-hydroxy-1-benzopyran-2(H)-one | 500215-87-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-methyl-3-[2'-cyclohexenyl]-4-hydroxy-1-benzopyran-2(H)-one
• 英文别名: 3-Cyclohex-2-en-1-yl-4-hydroxy-6-methylchromen-2-one
• CAS: 500215-87-2
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: DHIIATKDQULPRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-3-[2'-cyclohexenyl]-4-hydroxy-1-benzopyran-2(H)-one 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以90%的产率得到(1'S,5'S,9'S)-6-methyl-9'-iodo-2'-oxabicyclo[3,3,1]nonano[4',3'-c][1]benzopyran-2-one
  参考文献：
  名称：

  N-Iodosuccinimide mediated regioselective heterocyclization of 3-cyclohex-2′-enyl-4-hydroxycoumarin

  摘要：

  A number of 3-cyclohex-2'-enyl-4-hydroxy[1]benzopyran-2-ones are regioselectively cyclized by treatment with N-iodosuccinimide in acetonitrile to afford 9'-iodo-2'-oxabicyclo[3,3,I]nonano[4',3'-c][I]benzopyran-2-ones in excellent yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01024-4
• 作为产物：
  描述：

  4-羟基-6-甲基香豆素 、 3-溴环己烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以65%的产率得到6-methyl-3-[2'-cyclohexenyl]-4-hydroxy-1-benzopyran-2(H)-one
  参考文献：
  名称：

  N-Iodosuccinimide mediated regioselective heterocyclization of 3-cyclohex-2′-enyl-4-hydroxycoumarin

  摘要：

  A number of 3-cyclohex-2'-enyl-4-hydroxy[1]benzopyran-2-ones are regioselectively cyclized by treatment with N-iodosuccinimide in acetonitrile to afford 9'-iodo-2'-oxabicyclo[3,3,I]nonano[4',3'-c][I]benzopyran-2-ones in excellent yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01024-4

文献信息

• Stannic Chloride–Iodine: An Efficient Reagent for Regioselective Synthesis of Furan–Fused Heterocycles
  作者：K. C. Majumdar、A. Biswas、P. P. Mukhopadhyay

  DOI：10.1080/00397910701470982

  日期：2007.8.1

  SnCl4-I-2-mediated cyclization of ortho-cyclohexenyl phenol and ortho-cyclohexenyl enol derivatives of coumarin, uracil, dimedone, and pyrone at room temperature for 1 h give the linear cyclized products in 78-90% yield, which, on treatment with 10% Pd-C at 250 degrees C for 1-2 h, afford corresponding aromatized products in 80-84% yield.