(Z)-methyl 3-(5'-bromosalicyloylhydrazinocarbonyl)prop-2-enoate | 1257902-76-3

• 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: (Z)-methyl 3-(5'-bromosalicyloylhydrazinocarbonyl)prop-2-enoate
• CAS: 1257902-76-3
• 化学式: C₁₂H₁₁BrN₂O₅
• 分子量: 343.134
• InChiKey: MOOBQWXACWFEJM-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  甲醇 、 (Z)-3-(5'-bromosalicyloylhydrazinocarbonyl)prop-2-enoic acid 在 iron(III) chloride hexahydrate 、 吡啶 、 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 水 为溶剂， 反应 10.33h， 以88%的产率得到(Z)-methyl 3-(5'-bromosalicyloylhydrazinocarbonyl)prop-2-enoate
  参考文献：
  名称：

  Esterification and isolation of the carboxylic acid with salicyl-bis-hydrazide via coordination of iron(III) 18-metallacrown-6 complex

  摘要：

  The trianionic heptadentate ligand, (Z)-3-(5'-bromosalicylhydrazinocarbonyl) propenoic acid ((Z)-H4bshcpa), has been synthesized in good yield and reacted with FeCl3 center dot 6H2O to produce [FeIII6(C12H8N2O5Br)6(H2O)2(CH3OH)4] center dot 8H2O center dot 8CH3OH. The complex has been characterized by single-crystal X-ray diffraction. In the self-assembly process the ligand was esterified and transferred into (Z)-methyl 3-(5'-bromosalicylhydrazinocarbonyl) propenoate ((Z)-H3mbshcp). In the crystal structure, the neutral Fe(III) complex contains an 18-membered metallacrown ring consisting of six Fe(III) and six trianionic ligands. The 18-membered metallacrown ring is formed by six structural moieties of the type [Fe(III)-N-N]. Due to the meridional coordination of the ligands to Fe3+, the ligands enforce stereochemistry of the Fe3+ ions as a propeller configuration with alternating / forms. The metallacrown can be treated with SnCl2 to obtain purified ester. In addition, we have also obtained reduced esterified ligand, methyl 3-(5'-bromosalicylhydrazinocarbonyl) propanoate (H3mbshcp), with Zn powder as reductant.

  DOI：

  10.1080/00958972.2010.520706