4,4'-Bis(chloromethyl)-2,2'-bi-1,3-thiazole | 98557-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,4'-Bis(chloromethyl)-2,2'-bi-1,3-thiazole
• 英文别名: 4,4'-bis-(chloromethyl)-2,2'-bithiazole；4,4'-bis(chloromethyl)-2,2'-bithiazole；4,4'-bis-chloromethyl-[2,2']bithiazolyl；4,4'-Bis-chlormethyl-[2,2']bithiazolyl；4-(Chloromethyl)-2-[4-(chloromethyl)-1,3-thiazol-2-yl]-1,3-thiazole
• CAS: 98557-65-4
• 化学式: C₈H₆Cl₂N₂S₂
• 分子量: 265.187
• InChiKey: HMDIPHHNAKRLFC-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  445.3±53.0 °C(predicted)
• 密度：
  1.510±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-Bis(chloromethyl)-2,2'-bi-1,3-thiazole 在 正丁基锂 、 potassium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.5h， 生成 4,4'-bis-(4-pentenoxymethyl)-2,2'-bithiazole
  参考文献：
  名称：

  Intermolecular Interactions in π-Stacked Conjugated Molecules. Synthesis, Structure, and Spectral Characterization of Alkyl Bithiazole Oligomers

  摘要：

  Syntheses are reported of new 4,4'-dialkyl-2,2'-bithiazole oligomers that have alkenoxy side chains that are capable of easy conversion to oligomers with functionalized side chains, e.g., terminally substituted hydroxy chains. The crystal structures of two representative oligomers (4,4',4",4"'-tetra-(2-propenoxymethyl)2,2',5',5",2",2"'-quaterthiazole (3132) and 4,4',4",4"'-tetra-(3-hydroxypropyloxymethyl)-2,2',5',5",2",2"'quaterthiazole (3H2)) were determined; 3P2 crystallizes in a pi-stacked motif with two molecules per unit cell, whereas 3H2 forms pi-stacks that are linked with hydrogen bonds to form infinite two-dimensional sheets with one molecule per unit cell. A comparison of the UV-vis spectra of the compounds in solution and in the solid state provides unequivocal evidence for the presence of a Davyclov splitting, W-D approximate to 0.2 eV, in solid 3P2. The spectra are interpreted in the framework of molecular exciton theory to extract a value of the intermolecular transfer integral, J approximate to 0.2 eV, for a total exciton bandwidth of ca. 0.8 eV. Monte Carlo calculations were used to determine the density of states of the exciton band and the absorption and emission line shapes of the 0 <-- 0 transition. It is suggested that the "three-humped" absorption profile typical of partially crystalline, regioregular polymers is the "optical signature" of pi-stacking.

  DOI：

  10.1021/ja029216m
• 作为产物：
  描述：

  1,3-二氯丙酮 、 二硫代乙酰胺 在 calcium carbonate 作用下， 以 丙酮 为溶剂， 反应 22.0h， 以23%的产率得到4,4'-Bis(chloromethyl)-2,2'-bi-1,3-thiazole
  参考文献：
  名称：

  Intermolecular Interactions in π-Stacked Conjugated Molecules. Synthesis, Structure, and Spectral Characterization of Alkyl Bithiazole Oligomers

  摘要：

  Syntheses are reported of new 4,4'-dialkyl-2,2'-bithiazole oligomers that have alkenoxy side chains that are capable of easy conversion to oligomers with functionalized side chains, e.g., terminally substituted hydroxy chains. The crystal structures of two representative oligomers (4,4',4",4"'-tetra-(2-propenoxymethyl)2,2',5',5",2",2"'-quaterthiazole (3132) and 4,4',4",4"'-tetra-(3-hydroxypropyloxymethyl)-2,2',5',5",2",2"'quaterthiazole (3H2)) were determined; 3P2 crystallizes in a pi-stacked motif with two molecules per unit cell, whereas 3H2 forms pi-stacks that are linked with hydrogen bonds to form infinite two-dimensional sheets with one molecule per unit cell. A comparison of the UV-vis spectra of the compounds in solution and in the solid state provides unequivocal evidence for the presence of a Davyclov splitting, W-D approximate to 0.2 eV, in solid 3P2. The spectra are interpreted in the framework of molecular exciton theory to extract a value of the intermolecular transfer integral, J approximate to 0.2 eV, for a total exciton bandwidth of ca. 0.8 eV. Monte Carlo calculations were used to determine the density of states of the exciton band and the absorption and emission line shapes of the 0 <-- 0 transition. It is suggested that the "three-humped" absorption profile typical of partially crystalline, regioregular polymers is the "optical signature" of pi-stacking.

  DOI：

  10.1021/ja029216m

文献信息

• Synthesis and Properties of Macrobicyclic Cryptates Incorporating Five- and Six-Membered Biheteroaryl Units
  作者：Jean-Marie Lehn、Jean-Bernard Regnouf De Vains

  DOI：10.1002/hlca.19920750422

  日期：1992.6.24

  Treatment of the sodium complexes with europium(III) chloride gave the corresponding EuIII cryptates. The structural and spectral properties of these compounds are described. The EuIII complexes present characteristic 1H-NMR chemical-shift features. Their luminescence properties are described.

  大双环配体1-6的钠盐盐酸盐已通过直接大双环化或逐步方法合成。它们并入了2，2′-联噻唑，2，2′-联咪唑，2.2′-联嘧啶以及2，2′-联吡啶单元。用氯化euro（III）处理钠络合物得到相应的Eu III隐窝。描述了这些化合物的结构和光谱性质。Eu III配合物具有特征性的1 H-NMR化学位移特征。描述了它们的发光特性。
• Derivatives of pyridine and quinoline
  申请人：Lacal Sanjuan Juan Carlos

  公开号：US20070185170A1

  公开（公告）日：2007-08-09

  The invention provides compounds of formula I blocking phosphorylcholine biosynthesis by means of the selective blocking of the choline kinase enzyme in tumor cells or in cells affected by parasitic infection and therefore being applicable in the treatment of tumors and parasitic diseases or diseases produced by viruses and fungi in animals, including human beings; as well as to a method for preparing the compounds of the invention and certain intermediates of said method.

  本发明提供了I式化合物，通过选择性阻断肿瘤细胞或受寄生虫感染的细胞中的胆碱激酶酶的方式，阻断磷酸胆碱生物合成，因此可应用于治疗动物，包括人类中的肿瘤和寄生虫病或由病毒和真菌引起的疾病;以及一种制备本发明化合物和该方法的某些中间体的方法。
• PYRIDINIUM AND QUINOLINIUM DERIVATIVES
  申请人：Lacal Sanjuán Juan Carlos

  公开号：US20110178124A1

  公开（公告）日：2011-07-21

  The invention provides compounds of formula I blocking phosphorylcholine biosynthesis by means of the selective blocking of the choline kinase enzyme in tumor cells or in cells affected by parasitic infection and therefore being applicable in the treatment of tumors and parasitic diseases or diseases produced by viruses and fungi in animals, including human beings; as well as to a method for preparing the compounds of the invention and certain intermediates of said method.

  本发明提供了一种公式I的化合物，通过选择性阻断肿瘤细胞或受寄生虫感染的细胞中的胆碱激酶酶的方式阻断磷酸胆碱生物合成，因此可应用于治疗动物（包括人类）中的肿瘤和寄生虫病或由病毒和真菌引起的疾病；以及用于制备本发明化合物和该方法的某些中间体。
• Pyridinium and quinolinium derivatives as Choline kinase inhibitors
  申请人：Consejo Superior De Investigaciones Científicas

  公开号：EP2085386A2

  公开（公告）日：2009-08-05

  The invention provides compounds of formula I blocking phosphorylcholine biosynthesis by means of the selective blocking of the choline kinase enzyme in tumor cells or in cells affected by parasitic infection and therefore being applicable in the treatment of tumors and parasitic diseases or diseases produced by viruses and fungi in animals, including human beings; as well as to a method for preparing the compounds of the invention and certain intermediates of said method.

  本发明提供了通过选择性阻断肿瘤细胞或受寄生虫感染细胞中的胆碱激酶，从而阻断磷酸胆碱生物合成的式 I 化合物，因此适用于治疗肿瘤和寄生虫病或由病毒和真菌引起的动物（包括人类）疾病；以及制备本发明化合物的方法和所述方法的某些中间体。
• Synthesis of Macrobicyclic Cryptates incorporating Bithiazole, Bisimidazole and Bipyrimidine Binding Subunits
  作者：Jean-Marie Lehn、Jean-Bernard Regnouf de Vains

  DOI：10.1016/s0040-4039(00)99650-3

  日期：1989.1