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。
• Dipole Moments of 2- and 4-Substituted 9-Isothiocyanatoacridines
  作者：Ivan Danihel、Gejza Suchár、Pavol Kristian、Stanislav Böhm

  DOI：10.1135/cccc19961615

  日期：——

  Dipole moments of a series of 2- and 4-substituted 9-isothiocyanatoacridines were determined and compared with the values calculated by vector addition using bond and group dipole moments. The results are discussed from the viewpoint of geometrical and conformational structures of the compounds investigated.

  一系列2-和4-取代的9-异硫氰酸基蒽啉的偶极矩已被测定，并与使用键和基团偶极矩进行向量相加计算的值进行比较。从所研究化合物的几何和构象结构的观点讨论了结果。
• 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.