indole-3-carboxaldehyde-4-dimethylaminobenzoylhydrazone | 540789-01-3

• 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: indole-3-carboxaldehyde-4-dimethylaminobenzoylhydrazone
• 英文别名: 4-(dimethylamino)-N-(1H-indol-3-ylmethylideneamino)benzamide
• CAS: 540789-01-3
• 化学式: C₁₈H₁₈N₄O
• 分子量: 306.367
• InChiKey: SFWJHRFWDHCAEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  indole-3-carboxaldehyde-4-dimethylaminobenzoylhydrazone 、 copper(II) nitrate 以 二甲基亚砜 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Ultrasensitive turn-on fluorescence detection of Cu2+ based on p-dimethylaminobenzamide derivative and the application to cell imaging

  摘要：

  A new p-dimethylaminobenzamide derivative based compound BDIH has been synthesized. Cu2+ turned on the fluorescence of compound BDIH with a 1:2 binding stoichiometry. The fluorescent color of compound BDIH shows an evident change from colorless to bright blue upon the addition of Cu2+, which could be visibly detected by the naked eye under UV light at 365 nm. More importantly, the detection limit was found to be 0.64 nM which is far lower than the maximal allowed concentration of the WHO limit (31.5 mu M) for drinking water. This selective "turn-on" fluorescence sensor was used to identify Cu2+ in living cells using confocal fluorescence microscopy, indicating that compound BDIH has a potential application for selective detection of Cu2+ in organism. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2016.09.011
• 作为产物：
  描述：

  3-吲哚甲醛 、 对二甲氨基苯甲酰肼 以 乙醇 为溶剂， 反应 3.0h， 以86%的产率得到indole-3-carboxaldehyde-4-dimethylaminobenzoylhydrazone
  参考文献：
  名称：

  Ultrasensitive turn-on fluorescence detection of Cu2+ based on p-dimethylaminobenzamide derivative and the application to cell imaging

  摘要：

  A new p-dimethylaminobenzamide derivative based compound BDIH has been synthesized. Cu2+ turned on the fluorescence of compound BDIH with a 1:2 binding stoichiometry. The fluorescent color of compound BDIH shows an evident change from colorless to bright blue upon the addition of Cu2+, which could be visibly detected by the naked eye under UV light at 365 nm. More importantly, the detection limit was found to be 0.64 nM which is far lower than the maximal allowed concentration of the WHO limit (31.5 mu M) for drinking water. This selective "turn-on" fluorescence sensor was used to identify Cu2+ in living cells using confocal fluorescence microscopy, indicating that compound BDIH has a potential application for selective detection of Cu2+ in organism. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2016.09.011

文献信息

• Cyclopalladation of indole-3-carboxaldehyde aroylhydrazones
  作者：A.R. Balavardhana Rao、Samudranil Pal

  DOI：10.1016/j.jorganchem.2011.03.033

  日期：2011.7

  Reactions of PdCl2, LiCl, indole-3-carboxaldehyde 4-R-benzoylhydrazones (H2Ln; n = 1, 2, 3 and 4 for R = H, Cl, OMe and NMe2, respectively) and CH3COONa·3H2O in 1:2:1:1 mol ratio in methanol produce the cyclopalladated species of general formula [Pd(HLn)Cl] in 65–85% yields. The complexes have been characterized with the help of elemental analysis and spectroscopic (infrared, electronic and NMR) measurements

  PdCl 2，LiCl，吲哚-3-羧醛 -4 - R-苯甲酰hydr（H 2 L n；对于R  = H，Cl，OMe和NMe 2分别为n，1、2、3和4 ）和CH 3 COONa的反应·在甲醇中以1：2：1：1：1摩尔比的3H 2 O产生通式[Pd（HL n）Cl]的环钯化合物，产率为65-85％。借助元素分析和光谱（红外，电子和NMR）测量对复合物进行了表征。配合物的质子NMR光谱表明在（HL n）中吲哚部分的周边位置有palpalation-。的代表复杂的通过X射线晶体学确认所确定的分子结构围palladation和形成围绕由三齿（HL金属中心扭曲CNOCl正方形平面的Ñ）-和氯化物。