(E)-N′-(2-chloro-5-nitrobenzylidene)-2-(1H-indol-3-yl)acetohydrazide | 1445858-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-N′-(2-chloro-5-nitrobenzylidene)-2-(1H-indol-3-yl)acetohydrazide
• 英文别名: (e)-N'-(2-chloro-5-nitrobenzylidene)-2-(1h-indol-3-yl)acetohydrazide；N-[(E)-(2-chloro-5-nitrophenyl)methylideneamino]-2-(1H-indol-3-yl)acetamide
• CAS: 1445858-70-7
• 化学式: C₁₇H₁₃ClN₄O₃
• 分子量: 356.768
• InChiKey: NDEGSDHVBBHSLV-KEBDBYFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吲哚-3-乙酰肼 、 2-氯-5-硝基苯甲醛 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到(E)-N′-(2-chloro-5-nitrobenzylidene)-2-(1H-indol-3-yl)acetohydrazide
  参考文献：
  名称：

  Crystal structures and antibacterial activity of hydrazone derivatives from 1H-indol-3-acetohydrazide

  摘要：

  A series of three new hydrazone derivatives C22H19N3O2 (1), C17H13ClN4O3 (2), and C21H24N4O2 center dot CH4O (3) obtained by the condensation of H-1-indol-3-acetohydrazide with 2-methoxynaphthaldehyde, 2-chloro-5-nitrobenzaldehyde, and 4-diethylaminosalicylaldehyde, respectively, in methanol, ia prepared. The compounds are characterized by elemental analysis, IR spectra, H-1 NMR spectra, and single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P2(1)/n with unit cell dimensions a = 17.740(2) , b = 5.621(1) , c = 18.573(3) , beta = 92.659(2)A degrees, V = 1850.0(6) (3), Z = 4, R (1) = 0.0610 and wR (2) = 0.1155. Compound 2 crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 29.178(2) , b = 8.195(1) , c = 14.372(1) , beta = 109.446(2)A degrees, V = 3240.5(5) (3), Z = 8, R (1) = 0.0452 and wR (2) = 0.1028. Compound 3 crystallizes in the monoclinic space group Pc with unit cell dimensions a = 6.579(1) , b = 15.112(2) , c = 10.676(2) , beta = 90.030(2)A degrees, V = 1061.4(3) (3), Z = 2, R (1) = 0.0535 and wR (2) = 0.1123. The single crystal X-ray structural determination reveals that the molecules of the compounds are much twisted due to the lack of efficient conjugation. Preliminary biological tests indicate that the compounds are effective antibacterial material.

  DOI：

  10.1134/s0022476613010216

文献信息

• Crystal structures and antibacterial activity of hydrazone derivatives from 1H-indol-3-acetohydrazide
  作者：F. Zhi、N. Shao、Q. Wang、Y. Zhang、R. Wang、Y. Yang

  DOI：10.1134/s0022476613010216

  日期：2013.2

  A series of three new hydrazone derivatives C22H19N3O2 (1), C17H13ClN4O3 (2), and C21H24N4O2 center dot CH4O (3) obtained by the condensation of H-1-indol-3-acetohydrazide with 2-methoxynaphthaldehyde, 2-chloro-5-nitrobenzaldehyde, and 4-diethylaminosalicylaldehyde, respectively, in methanol, ia prepared. The compounds are characterized by elemental analysis, IR spectra, H-1 NMR spectra, and single crystal X-ray diffraction. Compound 1 crystallizes in the monoclinic space group P2(1)/n with unit cell dimensions a = 17.740(2) , b = 5.621(1) , c = 18.573(3) , beta = 92.659(2)A degrees, V = 1850.0(6) (3), Z = 4, R (1) = 0.0610 and wR (2) = 0.1155. Compound 2 crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 29.178(2) , b = 8.195(1) , c = 14.372(1) , beta = 109.446(2)A degrees, V = 3240.5(5) (3), Z = 8, R (1) = 0.0452 and wR (2) = 0.1028. Compound 3 crystallizes in the monoclinic space group Pc with unit cell dimensions a = 6.579(1) , b = 15.112(2) , c = 10.676(2) , beta = 90.030(2)A degrees, V = 1061.4(3) (3), Z = 2, R (1) = 0.0535 and wR (2) = 0.1123. The single crystal X-ray structural determination reveals that the molecules of the compounds are much twisted due to the lack of efficient conjugation. Preliminary biological tests indicate that the compounds are effective antibacterial material.