10-methyl-9-aminoacridinium iodide | 36141-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-methyl-9-aminoacridinium iodide
• 英文别名: 9-amino-10-methylacridin-10-ium iodide；9-amino-10-methylacridinium iodide；10-Methylacridin-9(10H)-imine--hydrogen iodide (1/1)；10-methylacridin-9-imine;hydroiodide
• CAS: 36141-84-1
• 化学式: C₁₄H₁₃N₂*I
• 分子量: 336.175
• InChiKey: NYNVVTBEOOINHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘 、 10-methyl-9-aminoacridinium iodide 以 氯仿 为溶剂， 生成 9-amino-10-methylacridinium triiodide
  参考文献：
  名称：

  Stability and molecular and crystal structure of 9-amino-10-methylacridinium triiodide

  摘要：

  Mixing of equimolar amounts of 9-amino-10-methylacridinium iodide and elemental iodine yields 9-amino-10-methylacridinium triiodide. The complexation in the organic cation iodide-elemental iodine system has been studied by spectrophotometry. The composition and the stability constant of the complex formed in a chloroform solution have been determined. The compound [C14H13N2](+)[I-3](-) has been isolated as dark red plate crystals and studied by X-ray diffraction. The structure is formed by linear I-3(-) anions and 9-amino-10-methylacridinium cations assembled through pi-pi stacking. The cations in the stacks are shifted by approximately one ring with respect to one another. The triiodide ion is linear, the average I-I bond length (2.915 angstrom) is close to the standard value. The stacking reflects the specific nature of the organic cation, while the presence of the I-3(-) counterion results in extension of the system of hydrogen bonds.

  DOI：

  10.1134/s0036023607090112
• 作为产物：
  描述：

  氨基吖啶 在 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 以69 %的产率得到10-methyl-9-aminoacridinium iodide
  参考文献：
  名称：

  Water‐Ice Microstructures and Hydration States of Acridinium Iodide Studied by Phosphorescence Spectroscopy

  摘要：

  Ice has been suggested to have played a significant role in the origin of life partly owing to its ability to concentrate organic molecules and promote reaction efficiency. However, the techniques for studying organic molecules in ice are absorption‐based, which limits the sensitivity of measurements. Here we introduce an emission‐based method to study organic molecules in water ice: the phosphorescence displays high sensitivity depending on the hydration state of an organic salt probe, acridinium iodide (ADI). The designed ADI aqueous system exhibits phosphorescence that can be severely perturbed when the temperature is higher than 110 K at a concentration of the order of 10‐5M, indicating changes in hydration for ADI. Using the ADI phosphorescent probe, it is found that the microstructures of water ice, i.e., crystalline vs. glassy, can be strongly dictated by a trace amount (as low as 10‐5M) of water‐soluble organic molecules. Consistent with cryoSEM images and temperature‐dependent Raman spectral data, the ADI is dehydrated in more crystalline ice and hydrated in more glassy ice. The current investigation serves as a starting point for using more sensitive spectroscopic techniques for studying water‐organics interactions at a much lower concentration and wider temperature range.

  DOI：

  10.1002/anie.202405314

文献信息

• Acheson, R. Morrin; Constable, Edwin C.; Wright, R. Gordon McR., Journal of Chemical Research, Miniprint, 1983, # 1, p. 101 - 132
  作者：Acheson, R. Morrin、Constable, Edwin C.、Wright, R. Gordon McR.、Taylor, Grahame M.

  DOI：——

  日期：——
• MIZUYAMA K.; TOMINAGA Y.; MATSUDA Y.; KOBAYASHI G., CHEM. AND PHARM. BULL., 1979, 27, NO 12, 2879-2889
  作者：MIZUYAMA K.、 TOMINAGA Y.、 MATSUDA Y.、 KOBAYASHI G.

  DOI：——

  日期：——
• [EN] NUCLEIC ACID BASED SENSOR AND METHODS THEREOF<br/>[FR] CAPTEUR À BASE D'ACIDE NUCLÉIQUE ET PROCÉDÉS ASSOCIÉS
  申请人：NAT CT FOR BIOLOG SCIENCES

  公开号：WO2015159122A1

  公开（公告）日：2015-10-22

  The present disclosure relates to a nucleic acid based sensor, comprising a sensing 5 module, a normalizing module and a targeting module. It also relates to a method of obtaining and targeting the sensor and its use to identify and optionally quantify a target in a specific cellular microenvironment.
• Stability and molecular and crystal structure of 9-amino-10-methylacridinium triiodide
  作者：M. S. Chernovyants、I. V. Burykin、Yu. A. Kirsanova、I. E. Tolpygin

  DOI：10.1134/s0036023607090112

  日期：2007.9

  Mixing of equimolar amounts of 9-amino-10-methylacridinium iodide and elemental iodine yields 9-amino-10-methylacridinium triiodide. The complexation in the organic cation iodide-elemental iodine system has been studied by spectrophotometry. The composition and the stability constant of the complex formed in a chloroform solution have been determined. The compound [C14H13N2](+)[I-3](-) has been isolated as dark red plate crystals and studied by X-ray diffraction. The structure is formed by linear I-3(-) anions and 9-amino-10-methylacridinium cations assembled through pi-pi stacking. The cations in the stacks are shifted by approximately one ring with respect to one another. The triiodide ion is linear, the average I-I bond length (2.915 angstrom) is close to the standard value. The stacking reflects the specific nature of the organic cation, while the presence of the I-3(-) counterion results in extension of the system of hydrogen bonds.
• Water‐Ice Microstructures and Hydration States of Acridinium Iodide Studied by Phosphorescence Spectroscopy
  作者：Hongping Liu、Hao Su、Ning Chen、Jie Cen、Jiajia Tan、Baicheng Zhang、Xiaoyu Chen、Aoyuan Cheng、Shengquan Fu、Xiaoguo Zhou、Shilin Liu、Xuepeng Zhang、Shiyong Liu、Yi Luo、Guoqing Zhang

  DOI：10.1002/anie.202405314

  日期：——

  Ice has been suggested to have played a significant role in the origin of life partly owing to its ability to concentrate organic molecules and promote reaction efficiency. However, the techniques for studying organic molecules in ice are absorption‐based, which limits the sensitivity of measurements. Here we introduce an emission‐based method to study organic molecules in water ice: the phosphorescence displays high sensitivity depending on the hydration state of an organic salt probe, acridinium iodide (ADI). The designed ADI aqueous system exhibits phosphorescence that can be severely perturbed when the temperature is higher than 110 K at a concentration of the order of 10‐5M, indicating changes in hydration for ADI. Using the ADI phosphorescent probe, it is found that the microstructures of water ice, i.e., crystalline vs. glassy, can be strongly dictated by a trace amount (as low as 10‐5M) of water‐soluble organic molecules. Consistent with cryoSEM images and temperature‐dependent Raman spectral data, the ADI is dehydrated in more crystalline ice and hydrated in more glassy ice. The current investigation serves as a starting point for using more sensitive spectroscopic techniques for studying water‐organics interactions at a much lower concentration and wider temperature range.