methyl (2E)-3-(2-fluoro-4,6-dimethoxyphenyl)acrylate | 214492-74-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2E)-3-(2-fluoro-4,6-dimethoxyphenyl)acrylate
• 英文别名: methyl (E)-3-(2-fluoro-4,6-dimethoxyphenyl)prop-2-enoate
• CAS: 214492-74-7
• 化学式: C₁₂H₁₃FO₄
• 分子量: 240.231
• InChiKey: FYMCYOUFXQCVEO-SNAWJCMRSA-N

物化性质

• 沸点：
  328.479±37.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.186±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2E)-3-(2-fluoro-4,6-dimethoxyphenyl)acrylate 在 copper(I) oxide 、 ammonium hydroxide 、 sodium hydroxide 、 碘 、 三溴化硼 、 potassium iodide 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 为溶剂， 反应 63.0h， 生成
  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 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 15.5h， 生成 methyl (2E)-3-(2-fluoro-4,6-dimethoxyphenyl)acrylate
  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

文献信息

• Biosynthesis of Angular Furanocoumarins: Mechanism and Stereochemistry of the Oxidative Dealkylation of Columbianetin to Angelicin inHeracleum mantegazzianum (Apiaceae)
  作者：Volker Stanjek、Wilhelm Boland

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

  日期：1998.9.9

  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.

表征谱图