5-fluorodiphenyl-iodonium-2-carboxylate | 1453081-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-fluorodiphenyl-iodonium-2-carboxylate
• CAS: 1453081-49-6
• 化学式: C₁₃H₈FIO₂
• 分子量: 342.108
• InChiKey: VXQDEJDAKVOZEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.68
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-fluorodiphenyl-iodonium-2-carboxylate 、 3-(3-amino-4-methoxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid methyl ester 在 copper diacetate 、 异丙醇 作用下， 以 水 为溶剂， 反应 12.0h， 以43%的产率得到2-[5-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-2-methoxyphenylamino]-4-fluorobenzoic acid
  参考文献：
  名称：

  Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone

  摘要：

  An alternative pathway for the biosynthesis of the fungal alkaloid necatorone has been studied using fluorine-labeled 3-(2-carboxyphenylamino)-L-tyrosine. Although no incorporation of this compound could be detected in feeding experiments with young specimens of Lactarius necator, an analogous 3-aminotyrosine derivative could be converted synthetically into the oxopyridoacridine core structure of necatorone. In experiments aimed at the synthesis of aaptamine-type alkaloids, an unprecedented cyclization of a 3-aminotyrosine-methyl propiolate adduct to a methyl isoquinoline-3-carboxylate was observed. A mechanism is proposed, in which C3 of the propiolate delivers C1 of the isoquinoline nucleus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.118
• 作为产物：
  描述：

  对氟苯甲醛 在 sodium chlorite 、 dipotassium peroxodisulfate 、 正丁基锂 、 硫酸 、 氨基磺酸 、 碘 、 N,N,N'-三甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 、 水 、 丙酮 为溶剂， 反应 10.17h， 生成 5-fluorodiphenyl-iodonium-2-carboxylate
  参考文献：
  名称：

  Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone

  摘要：

  An alternative pathway for the biosynthesis of the fungal alkaloid necatorone has been studied using fluorine-labeled 3-(2-carboxyphenylamino)-L-tyrosine. Although no incorporation of this compound could be detected in feeding experiments with young specimens of Lactarius necator, an analogous 3-aminotyrosine derivative could be converted synthetically into the oxopyridoacridine core structure of necatorone. In experiments aimed at the synthesis of aaptamine-type alkaloids, an unprecedented cyclization of a 3-aminotyrosine-methyl propiolate adduct to a methyl isoquinoline-3-carboxylate was observed. A mechanism is proposed, in which C3 of the propiolate delivers C1 of the isoquinoline nucleus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.118