2-[5-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-2-methoxyphenylamino]-4-fluorobenzoic acid | 1453081-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[5-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-2-methoxyphenylamino]-4-fluorobenzoic acid
• 英文别名: 4-fluoro-2-[2-methoxy-5-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]anilino]benzoic acid
• CAS: 1453081-50-9
• 化学式: C₂₃H₂₇FN₂O₇
• 分子量: 462.475
• InChiKey: LOHKHIDRYVMFNR-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[5-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-2-methoxyphenylamino]-4-fluorobenzoic acid 在 水 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到2-[5-(2-amino-2-carboxyethyl)-2-hydroxyphenylamino]-4-fluorobenzoic acid dihydrobromide
  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：

  methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-nitrophenyl)propanoate 在 palladium 10% on activated carbon 、 氢气 、 copper diacetate 、 异丙醇 作用下， 以 甲醇 、 水 为溶剂， 反应 30.0h， 生成 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