3-Hydroxy-4-(1-methyl-allyl)-chromen-2-one | 126113-32-4

• 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: 3-Hydroxy-4-(1-methyl-allyl)-chromen-2-one
• 英文别名: 4-But-3-en-2-yl-3-hydroxychromen-2-one
• CAS: 126113-32-4
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: YOHLBQSVOWGWFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  3-Hydroxy-4-(1-methyl-allyl)-chromen-2-one 以32%的产率得到
  参考文献：
  名称：

  Mitra Jayati, Kumar Mitra Alok, Indian J. Chem. B, 33 (1994) N 3, S 276-279

  摘要：

  DOI：
• 作为产物：
  描述：

  以 氯苯 为溶剂， 生成 3-Hydroxy-4-(1-methyl-allyl)-chromen-2-one
  参考文献：
  名称：

  通过9-内-trig环化模式通过钯催化的分子内Heck反应合成中等规模的杂环

  摘要：

  通过钯催化的分子内Heck反应，通过不寻常的9-内-trig 环化模式，已经开发出一种高效且高产的合成九元杂环骨架的方法。 分子内Heck反应-乙酸钯-9-内-trig -九元环-克莱森重排

  DOI：

  10.1055/s-0029-1217395

文献信息

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

  DOI：——

  日期：——
• MAJUNDAR, KRISHNA C.;KHAN, ABU T.;CHATTOPADHYSY, SHITAL K., HETEROCYCLES, 29,(1989) N, C. 1573-1576
  作者：MAJUNDAR, KRISHNA C.、KHAN, ABU T.、CHATTOPADHYSY, SHITAL K.

  DOI：——

  日期：——
• Mitra Jayati, Kumar Mitra Alok, Indian J. Chem. B, 33 (1994) N 3, S 276-279
  作者：Mitra Jayati, Kumar Mitra Alok

  DOI：——

  日期：——