4-(trifluoromethanesulfonyloxy)isophthalic acid diethyl ester | 489426-11-1

• 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: 4-(trifluoromethanesulfonyloxy)isophthalic acid diethyl ester
• 英文别名: Diethyl 4-(trifluoromethylsulfonyloxy)benzene-1,3-dicarboxylate
• CAS: 489426-11-1
• 化学式: C₁₃H₁₃F₃O₇S
• 分子量: 370.303
• InChiKey: DEYKPFUADCJYID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-(trifluoromethanesulfonyloxy)isophthalic acid diethyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium azide 、 四丁基氟化铵 、 水 、 sodium 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 61.5h， 生成 methyl (3aS,3bS,11bS)-2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-1H-pyrrolo[3,2-c]quinoline-8-carboxylate
  参考文献：
  名称：

  Aromatic Nucleophilic Substitution or CuI-Catalyzed Coupling Route to Martinellic Acid

  摘要：

  Condensation of beta-amino ester 8b with triflate 7 gives N-aryl amino ester 11, which is converted into 2-substituted 4-oxoquinoline 4 using an intramolecular Dieckmann reaction as the key step. CuI-mediated coupling of beta-amino ester 8a with 1,4-diiodobenzene followed by an intramolecular acylation and Pd-catalyzed carbonylation provide another manner to 4. Alkylation of 4 and subsequent reductive amination deliver the cyclic imine 14, which is transformed into triamine 3 by ordinary operations. Guanylation of 3 under mild condition followed by deprotection results in the synthesis of martinellic acid 1.

  DOI：

  10.1021/jo026125z
• 作为产物：
  描述：

  三氟甲磺酸酐 、 4-hydroxy-1,3-benzenedicarboxylic acid diethyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到4-(trifluoromethanesulfonyloxy)isophthalic acid diethyl ester
  参考文献：
  名称：

  Aromatic Nucleophilic Substitution or CuI-Catalyzed Coupling Route to Martinellic Acid

  摘要：

  Condensation of beta-amino ester 8b with triflate 7 gives N-aryl amino ester 11, which is converted into 2-substituted 4-oxoquinoline 4 using an intramolecular Dieckmann reaction as the key step. CuI-mediated coupling of beta-amino ester 8a with 1,4-diiodobenzene followed by an intramolecular acylation and Pd-catalyzed carbonylation provide another manner to 4. Alkylation of 4 and subsequent reductive amination deliver the cyclic imine 14, which is transformed into triamine 3 by ordinary operations. Guanylation of 3 under mild condition followed by deprotection results in the synthesis of martinellic acid 1.

  DOI：

  10.1021/jo026125z

文献信息

• Aromatic Nucleophilic Substitution or CuI-Catalyzed Coupling Route to Martinellic Acid
  作者：Dawei Ma、Chengfeng Xia、Jiqing Jiang、Jianhua Zhang、Wenjun Tang

  DOI：10.1021/jo026125z

  日期：2003.1.1

  Condensation of beta-amino ester 8b with triflate 7 gives N-aryl amino ester 11, which is converted into 2-substituted 4-oxoquinoline 4 using an intramolecular Dieckmann reaction as the key step. CuI-mediated coupling of beta-amino ester 8a with 1,4-diiodobenzene followed by an intramolecular acylation and Pd-catalyzed carbonylation provide another manner to 4. Alkylation of 4 and subsequent reductive amination deliver the cyclic imine 14, which is transformed into triamine 3 by ordinary operations. Guanylation of 3 under mild condition followed by deprotection results in the synthesis of martinellic acid 1.