2-chloro-9-isothiocyanatoacridine | 24698-84-8

• 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: 2-chloro-9-isothiocyanatoacridine
• 英文别名: 2-chloro-9-isothiocyanato-acridine；2-Chlor-9-isothiocyanatoacridin；Acridine, 2-chloro-9-isothiocyanato-
• CAS: 24698-84-8
• 化学式: C₁₄H₇ClN₂S
• 分子量: 270.742
• InChiKey: ZWGNEHLMAQDQND-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C(Solv: acetone (67-64-1))
• 沸点：
  478.2±15.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-9-isothiocyanatoacridine 以 乙醚 、 乙腈 为溶剂， 反应 2.0h， 生成 2'-methoxy-5'-methoxycarbonyl-spiro<2-chlorodihydroacridine 9(10H),4'-thiazoline>
  参考文献：
  名称：

  New Type of Spiro Heterocycles. A Convenient Synthesis of Spiro[dihydroacridine 9(10H), 4′-Thiazolines]

  摘要：

  A new type of Heterocycles, spiro[dihydroacridine 9(10H), 4'-thiazolines] has been prepared in good yields by the addition of sodium alkoxides to 9-isothiocyanatoacridines and subsequent cyclization of obtained iminothiocarbonates with alkyl bromoacetates at mild conditions.

  DOI：

  10.1080/00397919508011473
• 作为产物：
  描述：

  2,9-二氯吖啶 、 silver thiocyanate 以 甲苯 为溶剂， 生成 2-chloro-9-isothiocyanatoacridine
  参考文献：
  名称：

  Fluorescence Reagents for Labelling of Biomolecules. Part III. Study of the Reactions of 2- and 4-Substituted 9-Isothiocyanatoacridines with Glycine

  摘要：

  研究了2-和4-取代的9-异硫氰酸基吖啶-在缓冲水合二甲基甲酰胺中与甘氨酸的亲核加成反应动力学。加成产物VIII-XIV为N-(9-吖啶基硫氨酰)甘氨酸，通过红外、紫外、¹H核磁共振、质谱和荧光光谱进行表征。衍生物VIII、X和XII的荧光强度高于起始异硫氰酸酯，其中无取代化合物X的荧光最强。根据反应产物的性质和动力学特征讨论了反应机理。

  DOI：

  10.1135/cccc19941682

文献信息

• Reaction of O-Alkyl-N-substituted Iminothiocarbonates with Bromoacetyl Bromide. A General Method for the Synthesis of 3-Substituted 1,3-Thiazolidine-2,4-diones
  作者：Ján Imrich、Juraj Bernát、Pavol Kristian、Tatiana Bušová、Slávka Hočová

  DOI：10.1135/cccc19960432

  日期：——

  Reaction of sodium salts of O-methyl-N-substituted iminothiocarbonates with bromoacetyl bromide represents a new general method for preparation of 3-substituted 1,3-thiazolidine-2,4-diones in good yields and high purity. The structure of the synthesized products has been confirmed by ¹H NMR, ¹³C NMR, IR and mass spectroscopy as well as by independent synthesis.

  通过溴乙酰溴与甲基-O-取代亚硫代碳酸亚胺钠盐的反应，可以得到3-取代-1,3-噻唑啉-2,4-二酮，产率高且纯度高，这代表了一种新的通用制备方法。合成产物的结构已通过1H NMR、13C NMR、IR和质谱以及独立合成进行了确认。
• Fluorescence Reagents for Labelling of Biomolecules. Part I. Synthesis and Spectral Characterization of 2- and 4-Substituted 9-Isothiocyanatoacridines
  作者：Dana Mazagová、Danica Sabolová、Pavol Kristian、Ján Imrich、Marián Antalík、Dušan Podhradský

  DOI：10.1135/cccc19940203

  日期：——

  9-Isothiocyanatoacridines VIII - XIV were prepared from the corresponding 9-chloroacridines I - VII. The IR, ¹H NMR, ¹³C NMR and fluorescence spectra of the products are given. The ¹³C NMR chemical shifts of the C-9 ipso carbon atom exhibit a trend that is in accord with the Hammett constants of substituents bonded to the C-2 carbon. Effect of these substituents on the chemical shift of C-NCS was only small. The dependence of hydrolysis of isothiocyanates VIII - XIV on pH of the medium was studied. It was found that 9-isothiocyanatoacridines do not undergo hydrolysis at pH 7 - 10. The relative fluorescence intensities (F/F₀) of compounds VIII - XIV at pH 7.4 have been determined in comparison with that of 9-aminoacridine. No direct dependence between the fluorescence intensity and the polar character of substituents has been found.

  从相应的9-氯基蒽醌I-VII制备了9-异硫氰酸酯蒽醌VIII-XIV。给出了产物的红外线、1H NMR、13C NMR和荧光光谱。C-9 ipso碳原子的13C NMR化学位移呈现出与与C-2碳相连的取代基的Hammett常数相符合的趋势。这些取代基对C-NCS的化学位移的影响很小。研究了异硫氰酸酯VIII-XIV在介质pH值上的水解依赖性。发现9-异硫氰酸酯蒽醌在pH 7-10不会发生水解。与9-氨基蒽醌相比，确定了化合物VIII-XIV在pH 7.4下的相对荧光强度（F/F0）。没有发现荧光强度与取代基极性特征之间的直接关系。
• Fluorescence Reagents for Labelling of Biomolecules. Part III. Study of the Reactions of 2- and 4-Substituted 9-Isothiocyanatoacridines with Glycine
  作者：Danica Sabolová、Dana Mazagová、Pavol Kristian、Marián Antalík、Dušan Podhradský、Ján Imrich

  DOI：10.1135/cccc19941682

  日期：——

  Kinetics of nucleophilic addition reaction of 2- and 4-substituted 9-isothiocyanatoacridines I - VII with glycine in buffered aqueous dimethylformamide has been studied. The addition products, N-(9-acridinylthiocarbamoyl)glycines VIII - XIV, were characterized by IR, UV, ¹H NMR, mass and fluorescence spectra. Derivatives VIII, X and XII exhibited higher fluorescence intensity than the starting isothiocyanates; the highest fluorescence was found for the unsubstituted compound X. The reaction mechanism is discussed on the basis of properties of the reaction products and kinetic characteristics.

  研究了2-和4-取代的9-异硫氰酸基吖啶-在缓冲水合二甲基甲酰胺中与甘氨酸的亲核加成反应动力学。加成产物VIII-XIV为N-(9-吖啶基硫氨酰)甘氨酸，通过红外、紫外、¹H核磁共振、质谱和荧光光谱进行表征。衍生物VIII、X和XII的荧光强度高于起始异硫氰酸酯，其中无取代化合物X的荧光最强。根据反应产物的性质和动力学特征讨论了反应机理。
• Vlassa, M.; Kezdi, Maria; Bogdan, M., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 6, p. 1007 - 1010
  作者：Vlassa, M.、Kezdi, Maria、Bogdan, M.

  DOI：——

  日期：——
• Synthesis, Spectral Characterization and Fluorescence Properties of O-Methyl-S-alkyl-N-(9-acridinyl)iminothiocarbonates
  作者：Pavol Kristian、Juraj Bernát、Dana Mazagová、Marián Antalík

  DOI：10.3987/com-94-s78

  日期：——

  A simple method for preparation of O-methyl-S-alkyl-N-(9-acridinyl)iminothio-carbonates via addition of sodium methoxide to 9-isothiocyanatoacridines (1a-1d) and subsequent alkylation of formed sodium salts (2a-2d) with methyl iodide and butyl bromide has been elaborated.