6-iodo-7-hydroxycoumarin | 142429-27-4

• 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: 6-iodo-7-hydroxycoumarin
• 英文别名: 7-Hydroxy-6-iodochromen-2-one
• CAS: 142429-27-4
• 化学式: C₉H₅IO₃
• 分子量: 288.041
• InChiKey: CEXXLVQOIZYYSU-UHFFFAOYSA-N

物化性质

• 沸点：
  370.1±42.0 °C(Predicted)
• 密度：
  2.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-iodo-7-hydroxycoumarin 在 吡啶 、 异丙基氯化镁 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.67h， 生成 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：

  7-甲氧基香豆素 在 ammonium hydroxide 、 碘 、 sodium methylate 、 三溴化硼 、 potassium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 44.0h， 生成 6-iodo-7-hydroxycoumarin
  参考文献：
  名称：

  An efficient synthesis of furanocoumarins

  摘要：

  An efficient synthesis of linear and angular furanocoumarins has been carried out starting from iodoumbelliferone derivatives. First synthesis of 6-iodoumbelliferone is described. The average yields are higher than those reported before.

  DOI：

  10.1016/s0040-4020(01)92200-8

文献信息

• A mild and simple regioselective iodination of activated aromatics with iodine and catalytic ceric ammonium nitrate
  作者：Biswanath Das、Maddeboina Krishnaiah、Katta Venkateswarlu、V. Saidi Reddy

  DOI：10.1016/j.tetlet.2006.11.009

  日期：2007.1

  Molecular iodine in the presence of a catalytic amount of CAN has been utilized efficiently for regioselective iodination of activated aromatic compounds under mild reaction conditions.

  在催化量的CAN的存在下，分子碘已被有效地用于在温和的反应条件下对活化的芳香族化合物进行区域选择性碘化。
• Stereoselective syntheses of deuterium labelled marmesins; valuable metabolic probes for mechanistic studies in furanocoumarin biosynthesis
  作者：Volker Stanjek、Martin Miksch、Wilhelm Boland

  DOI：10.1016/s0040-4020(97)10237-x

  日期：1997.12

  Stereoselective syntheses of deuterium labelled marmesins 3a-3e as metabolic probes for biosynthetic studies are described. Starting from iodo-umbelliferone (5), the title compounds were readily available by copper catalysed alkylation-cyclisation and subsequent transfer-hydrogenation of the resulting furanocoumarins 6a-6e. The bioconversion of marmesin by a microsomal preparation of A. majus yielded psoralene (4) and acetone in a single step and proceeded as a syn-elimination of the alkoxy-substituent together with a single hydrogen atom from a vicinal carbon atom (beta-cleavage). (C) 1997 Elsevier Science Ltd.
• An efficient synthesis of furanocoumarins
  作者：Eva Zubía、Francisco Rodríguez Luis、Guillermo M. Massanet、Isidro G. Collado

  DOI：10.1016/s0040-4020(01)92200-8

  日期：1992.1

  An efficient synthesis of linear and angular furanocoumarins has been carried out starting from iodoumbelliferone derivatives. First synthesis of 6-iodoumbelliferone is described. The average yields are higher than those reported before.
• 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
  作者：Yefen Zou、Mercedes Lobera、Barry B. Snider

  DOI：10.1021/jo047974k

  日期：2005.3.1

  [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.