4-allyl-3-hydroxycoumarin | 23891-03-4

• 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: 4-allyl-3-hydroxycoumarin
• 英文别名: 3-Hydroxy-4-prop-2-enylchromen-2-one
• CAS: 23891-03-4
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: WGMXWFSUSOBNDO-UHFFFAOYSA-N

物化性质

• 熔点：
  149 °C
• 沸点：
  382.1±42.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4-allyl-3-hydroxycoumarin 在 双(乙腈)氯化钯(II) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以40%的产率得到2-Methylfuro<2,3-c><1>benzopyran-4-one
  参考文献：
  名称：

  Mitra, Jayati; Mitra, Alok Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, p. 276 - 279

  摘要：

  DOI：
• 作为产物：
  描述：

  3-allyloxycoumarin 以 氯苯 为溶剂， 反应 8.0h， 生成 4-allyl-3-hydroxycoumarin
  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

• Combined Claisen rearrangement and ring-closing metathesis as a route to oxepin- and oxocin-annulated coumarins
  作者：Shital K. Chattopadhyay、Susama Maity、Srikanta Panja

  DOI：10.1016/s0040-4039(02)01806-3

  日期：2002.10

  A new route involving a tandem Claisen rearrangement and ring-closing metathesis reaction has been developed for the synthesis of some hitherto unknown oxepin- and oxocin-annulated coumarin derivatives.

  已经开发了一种涉及串联克莱森重排和闭环易位反应的新途径，用于合成一些迄今未知的氧杂庚酸酯和氧辛酸环化的香豆素衍生物。
• 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。
• Sequential Claisen Rearrangement and Intramolecular Heck Reaction as a Route to Medium-Ring Oxacycle-Fused Heterocycles
  作者：Shital Chattopadhyay、Kaushik Neogi、Sovan Singha、Rajat Dey

  DOI：10.1055/s-2008-1072719

  日期：2008.5

  A synthetic strategy based on tandem application of Claisen rearrangement and intramolecular Heck reaction as key steps has been developed for the synthesis of various hitherto unknown benzoxocine- and benzoxonine-fused coumarin and quinolone derivatives.

  已经开发了一种基于串联应用 Claisen 重排和分子内 Heck 反应作为关键步骤的合成策略，用于合成各种迄今为止未知的苯佐辛和苯佐宁稠合香豆素和喹诺酮衍生物。
• Mitra, Jayati; Mitra, Alok K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 9, p. 613 - 616
  作者：Mitra, Jayati、Mitra, Alok K

  DOI：——

  日期：——
• Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins
  作者：James A. Bull、Cristina Luján、Michael G. Hutchings、Peter Quayle

  DOI：10.1016/j.tetlet.2009.03.077

  日期：2009.7

  A new approach to the synthesis of the 6H-benzo[d]naphthal[,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. (C) 2009 Elsevier Ltd. All rights reserved.