Ethyl 5-fluoro-2-oxofuro[2,3-h]chromene-8-carboxylate | 214492-80-5

• 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: Ethyl 5-fluoro-2-oxofuro[2,3-h]chromene-8-carboxylate
• CAS: 214492-80-5
• 化学式: C₁₄H₉FO₅
• 分子量: 276.221
• InChiKey: JXZXYPZUACWKQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 5-fluoro-2-oxofuro[2,3-h]chromene-8-carboxylate 在 sodium hydroxide 、 铜 作用下， 以 喹啉 、 水 为溶剂， 反应 3.0h， 生成 5-Fluoroangelicin
  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 copper(I) oxide 、 ammonium hydroxide 、 碘 、 三溴化硼 、 potassium iodide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 76.5h， 生成 Ethyl 5-fluoro-2-oxofuro[2,3-h]chromene-8-carboxylate
  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