5-Fluoro-7-hydroxy-2H-1-benzopyran-2-one | 214492-75-8

• 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: 5-Fluoro-7-hydroxy-2H-1-benzopyran-2-one
• 英文别名: 5-fluoro-7-hydroxychromen-2-one
• CAS: 214492-75-8
• 化学式: C₉H₅FO₃
• 分子量: 180.135
• InChiKey: YAFNNKGPKRRRCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  4

反应信息

• 作为反应物：
  描述：

  5-Fluoro-7-hydroxy-2H-1-benzopyran-2-one 在 palladium on activated charcoal copper(I) oxide 、 ammonium hydroxide 、 diclazuril 、 氢气 、 碘 、 potassium iodide 作用下， 以 1,4-二氧六环 、 吡啶 、 氘代甲醇-d 、 水 、 重水 、 丙酮 为溶剂， 反应 7.0h， 生成 (+/-)-cis-5-fluoro-3,4,8,9-tetrahydro-8-(1-hydroxy-1-methylethyl)(9-2H)angelicin
  参考文献：
  名称：

  Biosynthesis of Angular Furanocoumarins: Mechanism and Stereochemistry of the Oxidative Dealkylation of Columbianetin to Angelicin inHeracleum mantegazzianum (Apiaceae)

  摘要：

  Deuterium-labelled 5-fluorocolumbianetin 13 was synthesized as a metabolic probe to examine the stereochemical course of the bioconversion of (+)-columbianetin (12) into the angular furocoumarin angelicin (5). In leaves of Heracleum mantegazzianum, oxidative dealkylation of the specifically deuterated fluorocolumbianetin 13 proceeded by syn-elimination of a D-atom, from C(9), and the vicinal 1-hydroxy-1-methylethyl substituent, yielding 5-fluoroangelicin (23). This matches the stereochemical course of the related reaction converting (+)-marmesin (10) into the linear furocoumarin psoralen (1). Key steps in the synthesis of 5-fluorocolumbianetin (13) were the copper-catalysed alkynylation/cyclization of 5-fluoro-8-iedoumbelliferone (15) followed by a transfer hydrogenation, which established the cis-orientation of the D-Atom and the 1-hydroxy-1-methylethyl substituent.

  DOI：

  10.1002/(sici)1522-2675(19980909)81:9<1596::aid-hlca1596>3.0.co;2-f
• 作为产物：
  描述：

  1,3-二甲氧基-5-氟苯 在 三溴化硼 、 三氯氧磷 作用下， 以 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 51.5h， 生成 5-Fluoro-7-hydroxy-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Biosynthesis of Angular Furanocoumarins: Mechanism and Stereochemistry of the Oxidative Dealkylation of Columbianetin to Angelicin inHeracleum mantegazzianum (Apiaceae)

  摘要：

  Deuterium-labelled 5-fluorocolumbianetin 13 was synthesized as a metabolic probe to examine the stereochemical course of the bioconversion of (+)-columbianetin (12) into the angular furocoumarin angelicin (5). In leaves of Heracleum mantegazzianum, oxidative dealkylation of the specifically deuterated fluorocolumbianetin 13 proceeded by syn-elimination of a D-atom, from C(9), and the vicinal 1-hydroxy-1-methylethyl substituent, yielding 5-fluoroangelicin (23). This matches the stereochemical course of the related reaction converting (+)-marmesin (10) into the linear furocoumarin psoralen (1). Key steps in the synthesis of 5-fluorocolumbianetin (13) were the copper-catalysed alkynylation/cyclization of 5-fluoro-8-iedoumbelliferone (15) followed by a transfer hydrogenation, which established the cis-orientation of the D-Atom and the 1-hydroxy-1-methylethyl substituent.

  DOI：

  10.1002/(sici)1522-2675(19980909)81:9<1596::aid-hlca1596>3.0.co;2-f