5-fluoro-8-(1-hydroxy-1-methylethyl)(9-2H)angelicin | 214492-77-0

• 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-8-(1-hydroxy-1-methylethyl)(9-2H)angelicin
• 英文别名: 9-deuterio-5-fluoro-8-(2-hydroxypropan-2-yl)furo[2,3-h]chromen-2-one
• CAS: 214492-77-0
• 化学式: C₁₄H₁₁FO₄
• 分子量: 263.229
• InChiKey: XOEYOBYDNFYAFE-UICOGKGYSA-N

物化性质

• 沸点：
  442.113±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.411±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.58
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-fluoro-8-(1-hydroxy-1-methylethyl)(9-2H)angelicin 在 甲酸 、 三乙胺 作用下， 以8%的产率得到(+/-)-cis-5-fluoro(9-2H)columbianetin
  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 、 diclazuril 、 碘 、 三溴化硼 、 potassium iodide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 吡啶 、 正己烷 、 二氯甲烷 、 氘代甲醇-d 、 水 、 重水 、 乙腈 为溶剂， 反应 54.5h， 生成 5-fluoro-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