2-Iodomethyl-6-methyl-2,3-dihydro-furo[3,2-c]pyran-4-one | 896132-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-Iodomethyl-6-methyl-2,3-dihydro-furo[3,2-c]pyran-4-one
• 英文别名: 2-(Iodomethyl)-6-methyl-2,3-dihydrofuro[3,2-c]pyran-4-one
• CAS: 896132-42-6
• 化学式: C₉H₉IO₃
• 分子量: 292.073
• InChiKey: NUVKASGWCFWBHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Iodomethyl-6-methyl-2,3-dihydro-furo[3,2-c]pyran-4-one 在 Montmorillonite K-10 clay 作用下， 反应 0.03h， 以96%的产率得到3-Iodo-7-methyl-3,4-dihydro-2H-pyrano[4,3-b]pyran-5-one
  参考文献：
  名称：

  Solid‐State Regioselective Cyclization Initiated by the Electrophilic Attack on the Double Bond by N‐Bromosuccinimide on Montmorillonite K‐10 Clay Support under Microwave Irradiation

  摘要：

  3-AllyI-4-hydroxy-coumarins and pyrones were regioselectively cyclized with N-bromosuccinimide (NBS) on solid phase under microwave irradiation in excellent yield. NBS on montmorillonite K-10 clay under microwave irradiation for expeditious solvent-free regioselective cyclization has been used for the first time.

  DOI：

  10.1080/00397910701228992
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 在 碘 、 四氯化锡 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 2-Iodomethyl-6-methyl-2,3-dihydro-furo[3,2-c]pyran-4-one
  参考文献：
  名称：

  SnCl₄–I₂ mediated regioselective 6-endo- and 5-exo-cyclization of ortho-allylenols

  摘要：

  3-烯丙基-4-羟基香豆素和4-烯丙基-3-羟基香豆素通过对应醚的热[3,3] sigmatropic重排反应以90%-92%的收率得到。3-烯丙基-4-羟基-6-甲基吡喃通过4-羟基-6-甲基吡喃与烯丙基卤化物的直接烷基化得到。这些底物在与SnCl4-I2在25°C处理时会产生一种既有5-内环反应产物又有6-外环反应产物的混合物。然而，当反应在较低温度（0-5°C，动力学控制）下进行时，观察到5-外环产物的选择性形成，而在较高温度（50°C，热力学控制）下进行的反应则选择性地生成6-内环产物。关键词：氯化锡、碘、克莱森重排反应、6-内环化、5-外环化、动力学控制反应、热力学控制反应。

  DOI：

  10.1139/v05-212

文献信息

• A Green Synthesis of Angularly Fused Furano-Pyrone/Coumarin and Quinolone Derivatives via Molecular Iodine-Mediated 5-exo-trig Cyclization in Aqueous Micelles
  作者：K. Majumdar、Debankan Ghosh、Shovan Mondal

  DOI：10.1055/s-0030-1258394

  日期：2011.2

  A simple, economical, and green approach to the synthesis of angularly fused furano- pyrone/coumarin and quinolone derivatives by molecular iodine-mediated 5-exo-trig cyclization using sodium dodecyl sulfate (SDS) as surfactant in water is described.

  本文介绍了一种简单、经济、绿色的方法，即在水中使用十二烷基硫酸钠（SDS）作为表面活性剂，通过碘分子介导的 5-外-三环合成角融合的呋喃酮/香豆素和喹诺酮衍生物。
• SnCl₄–I₂ mediated regioselective 6-endo- and 5-exo-cyclization of <i>ortho</i>-allylenols
  作者：K C Majumdar、A Biswas、P P Mukhopadhyay

  DOI：10.1139/v05-212

  日期：2005.12.1

  3-Allyl-4-hydroxycoumarins and 4-allyl-3-hydroxycoumarins are obtained in 90%–92% yields by the thermal [3,3] sigmatropic rearrangement of the corresponding ethers. 3-Allyl-4-hydroxy-6-methylpyrone is obtained from the direct alkylation of 4-hydroxy-6-methylpyrone with allyl halide. These substrates on treatment with SnCl₄–I₂ at 25 °C give a mixture of both 5-exo- and 6-endo-cyclization products. However, regioselective formation of 5-exo products is observed when the reactions are conducted at lower temperatures (0–5 °C, kinetically controlled), while the reaction at a higher temperature (50 °C, thermodynamically controlled) affords regioselectively 6-endo cyclization products.Key words: stannic chloride, iodine, claisen rearrangement, 6-endocyclization, 5-exocyclization, kinetically controlled reaction, thermodynamically controlled reaction.

  3-烯丙基-4-羟基香豆素和4-烯丙基-3-羟基香豆素通过对应醚的热[3,3] sigmatropic重排反应以90%-92%的收率得到。3-烯丙基-4-羟基-6-甲基吡喃通过4-羟基-6-甲基吡喃与烯丙基卤化物的直接烷基化得到。这些底物在与SnCl4-I2在25°C处理时会产生一种既有5-内环反应产物又有6-外环反应产物的混合物。然而，当反应在较低温度（0-5°C，动力学控制）下进行时，观察到5-外环产物的选择性形成，而在较高温度（50°C，热力学控制）下进行的反应则选择性地生成6-内环产物。关键词：氯化锡、碘、克莱森重排反应、6-内环化、5-外环化、动力学控制反应、热力学控制反应。
• Solid‐State Regioselective Cyclization Initiated by the Electrophilic Attack on the Double Bond by N‐Bromosuccinimide on Montmorillonite K‐10 Clay Support under Microwave Irradiation
  作者：K. C. Majumdar、H. Rahaman、B. Roy

  DOI：10.1080/00397910701228992

  日期：2007.5

  3-AllyI-4-hydroxy-coumarins and pyrones were regioselectively cyclized with N-bromosuccinimide (NBS) on solid phase under microwave irradiation in excellent yield. NBS on montmorillonite K-10 clay under microwave irradiation for expeditious solvent-free regioselective cyclization has been used for the first time.