(2S,3S)-3-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one | 849144-95-2

• 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: (2S,3S)-3-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• 英文别名: xanthoarnol；(2S,3S)-3-hydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• CAS: 849144-95-2
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: AIQSGHBQRRSBCN-STQMWFEESA-N

物化性质

• 沸点：
  469.4±45.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以100%的产率得到补骨脂素
  参考文献：
  名称：

  Synthesis of 2,3-Dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from Epoxy Aldehydes. One-Step Syntheses of Brosimacutin G, Vaginidiol, Vaginol, Smyrindiol, Xanthoarnol, and Avicenol A. Biomimetic Syntheses of Angelicin and Psoralen

  摘要：

  [GRAPHICS]We have developed two practical one-step syntheses of 2,3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure alpha,beta-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen.

  DOI：

  10.1021/jo047974k
• 作为产物：
  描述：

  6-iodo-7-hydroxycoumarin 在 吡啶 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2S,3S)-3-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one
  参考文献：
  名称：

  Synthesis of 2,3-Dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from Epoxy Aldehydes. One-Step Syntheses of Brosimacutin G, Vaginidiol, Vaginol, Smyrindiol, Xanthoarnol, and Avicenol A. Biomimetic Syntheses of Angelicin and Psoralen

  摘要：

  [GRAPHICS]We have developed two practical one-step syntheses of 2,3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure alpha,beta-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen.

  DOI：

  10.1021/jo047974k