α-hydroximido-(2-benzothiazolyl)acetonitrile | 75407-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: α-hydroximido-(2-benzothiazolyl)acetonitrile
• 英文别名: α-oximino-(2-benzothiazolyl)acetonitrile；2-isonitroso-2-(2-benzothiazolyl)acetonitrile；benzothiazolylcyanoxime；H(BTCO)；HBTCO；alpha-[Benzthiazol-2-yl]-alpha-oximino-acetonitrile；2-(1,3-benzothiazol-2-yl)-2-hydroxyiminoacetonitrile
• CAS: 75407-99-7
• 化学式: C₉H₅N₃OS
• mdl: MFCD01784761
• 分子量: 203.224
• InChiKey: USOUGMJKPPEOEY-UHFFFAOYSA-N

物化性质

• 沸点：
  407.4±28.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  thallium(I) carbonate 、 α-hydroximido-(2-benzothiazolyl)acetonitrile 以 水 为溶剂， 以72%的产率得到thallium(I) α-oximino-(2-benzothiazolyl)acetonitrile
  参考文献：
  名称：

  Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: new room temperature blue emitters

  摘要：

  合成了一系列五种2-杂芳腈氧肟酸，包括：α-氧肟基-(2-苯并咪唑基)乙腈（HBIHCO）、α-氧肟基-(N-甲基-2-苯并咪唑基)乙腈（HBIMCO）、α-氧肟基-(2-苯并噻唑基)乙腈（HBTCO）和α-氧肟基-(2-喹啉基)乙腈（HQCO）以及它们的单价铊(I) комплексы。采用光谱方法（1H、13C NMR、红外、紫外可见、质谱）和X射线分析对其进行了表征。HBIMCO（作为单水合物）在固态中采用平面反式反式构型。“HBOCO”的晶体结构揭示了存在亚硝基阴离子a（BOCO−）和质子化的氧肟阳离子b（H2BOCO+），它们在单元胞中形成氢键二聚体。这两种分子均采用平面结构，但配置不同：分子a为顺反构型，而b为反式反式构型。这是首次报告在氧肟中发现了两亲离子对，并且同一晶体中共存的两种几何顺/反异构体。所有2-杂芳腈氧肟酸在去质子化后形成黄色阴离子，在溶液中表现出显著的负溶剂色变效应。在Tl2CO3的热水溶液与固态质子化2-杂芳腈氧肟酸HL之间发生的非均相反应生成黄色的TlL。Tl(BTCO)的晶体结构显示形成了中心对称的二聚体，这些二聚体相互连接形成双链一维配位聚合物。氧肟基团的氧原子在三个不同的铊(I)中心之间起桥接作用。该阴离子在复合物中是非平面的，并采用反式反式构型。复杂中的聚合物结构呈现梯子型结构。苯并噻唑基之间错叠的π–π相互作用为结构提供了额外的稳定性。无论是有机配体还是它们的Tl(I)复合物在固态下均表现出强烈的室温蓝色发光。

  DOI：

  10.1039/b803846e
• 作为产物：
  描述：

  sodium nitrite 、 苯并噻唑-2-乙腈 在 水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 α-hydroximido-(2-benzothiazolyl)acetonitrile
  参考文献：
  名称：

  Thiadiazolyl-glyoxylonitrile-2-oxime ether derivatives for protecting

  摘要：

  本发明描述了一种保护耕作植物免受侵蚀性农业化学品的过程，其中使用式为##STR1##的氧化物衍生物作为解毒剂。可以将这些氧化物衍生物作为外衣剂处理耕作植物的耕作区域、耕作植物本身或植物的部分（种子、块茎、茎部等），根据需要进行处理。

  公开号：

  US04715883A1

文献信息

• Synthesis and crystal structure of a thallium (I) hydrogen benzothiazolylcyanoximate complex with 18-crown-6: the thallium atom is in the center of the crown ether cavity
  作者：K.V. Domasevitch、V.V. Skopenko、J. Sieler

  DOI：10.1016/0020-1693(96)05087-6

  日期：1996.8

  Complexes of composition [Tl(18-crown-6)BTCO}] and [Tl(18-crown-6)H(BTCO)2}] (BTCO=ONC(CN)-(benzothiazolyl-2)}su−) have been prepared. The crystal and molecular structure of the [Tl(18-crown-6)H(BTCO)2}] complex has been determined from X-ray diffraction data (orthorhommbic, space group Pbca, with a=15.520(3), b=11.668(2), c=19.661(4) A, V=3560.4(12) A3, Z=4). The structure was refined by least-squares

  组成为[Tl（18-crown-6）BTCO}]和[Tl（18-crown-6）H（BTCO）2}]的复合物（BTCO = ONC（CN）-（benzothiazolyl-2）} su −）已经准备好。[Tl（18-crown-6）H（BTCO）2}]配合物的晶体和分子结构已通过X射线衍射数据确定（正交，空间群Pbca，a = 15.520（3），b = 11.668（2），c = 19.661（4）A，V = 3560.4（12）A3，Z = 4）。通过最小二乘法将结构精炼为最终值R = 0.029，基于2525次独立反射，其中1>2σ（1）。金属原子占据对称中心。晶格由中心对称阳离子Tl（18-crown-6）+和阴离子[H（BTCO）2}-组成，它们是相邻阳离子之间的桥，以提供一维聚合物结构。atoms原子采用带有轴向腈氮原子的略微变形的六方双锥体几何结构的八倍配位，并精确地位于冠醚的中心（TlO〜2
• Benzoxazolyl-glyoxylonitrile-2-oxime ether derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04347372A1

  公开（公告）日：1982-08-31

  A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxime derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts and the like), as desired, can be treated with these oxime derivatives, which are used as a dressing.

  本发明涉及一种保护栽培植物免受侵害性农业化学品的方法，其中使用式为##STR1##的肟衍生物作为解毒剂。可以将栽培区域、栽培植物本身或植物的部分（种子、块茎、茎部等）按需用这些肟衍生物进行处理，作为一种覆盖剂。
• Light Insensitive Silver(I) Cyanoximates As Antimicrobial Agents for Indwelling Medical Devices
  作者：Nikolay Gerasimchuk、Andrzej Gamian、Garrett Glover、Bogumila Szponar

  DOI：10.1021/ic100830x

  日期：2010.11.1

  Ten silver(I) cyanoximates of AgL composition (L = NC-C(NO)-R, where R is electron withdrawing groups: -CN, -C(O)NR2, -C(O)R' (alkyl), -C(O)OEt, 2-heteroaryl fragments such as 2-pyridyl, 2-benzimidazolyl, 2-benzoxazolyl, 2-benzthiazolyl) were synthesized and characterized using spectroscopic methods and X-ray analysis. Crystal structures of four complexes were determined and revealed the formation of two-dimensional (2D) coordination polymers of different complexity in which anions exhibit bridging or combined chelate and bridging binding modes. In these compounds, anions are in the nitroso form. All studied AgL complexes are sparingly soluble in water and are thermally stable to 150 degrees C Synthesized compounds demonstrated remarkable insensitivity toward visible light and UV-radiation, which was explained based on their polymeric structures with multiple covalent bonds between bridging cyanoxime ligands and Ag(I) centers. All 10 silver(I) cyanoximates were tested in vitro on the subject of their antimicrobial activity against both Gram-positive and Gram-negative microorganisms such as Escherichia coli, Klebsiella pneumoniae, Proteus sp., Pseudomonas aeruginosa, Enterococcus hirae, Streptococcus mutans, Staphylococcus aureus, and Mycobacterium fortuitum as well as against Candida albicans in solutions, and in the solid state as pressed pellets and dried filter paper disks presoaked with solutions of AgL in DMF. Results showed pronounced antimicrobial activity for all investigated complexes. A combination of five factors: (1) light insensitivity, (2) poor water solubility, (3) high thermal stability, (4) lack of toxicity of organic ligands, and (5) in vitro antimicrobial activity allows development of silver(I) cyanoximates for medical applications. These include antimicrobial additives to acrylate glue, cured by UV-radiation, used in introduction of prosthetic joints and dental implants, and prevention of biofilm formation on several types of indwelling medical devices.
• Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: new room temperature blue emitters
  作者：Olesya T. Ilkun、Stephen J. Archibald、Charles L. Barnes、Nikolay Gerasimchuk、Richard Biagioni、Svitlana Silchenko、Olga A. Gerasimchuk、Victor N. Nemykin

  DOI：10.1039/b803846e

  日期：——

  A series of five 2-heteroarylcyanoximes such as: α-oximino-(2-benzimidazolyl)acetonitrile (HBIHCO), α-oximino-(N-methy-l-2-benzimidazolyl)acetonitrile (HBIMCO), α-oximino-(2-benzoxazolyl)acetonitrile (HBOCO), α-oximino-(2-benzothiazolyl)acetonitrile (HBTCO) and α-oximino-(2-quinolyl)acetonitrile (HQCO) and their monovalent thallium(I) complexes were synthesized and characterized using spectroscopic methods (1H, 13C NMR, IR, UV-visible, mass-spectrometry) and X-ray analysis. The HBIMCO (as monohydrate) adopts planar trans-anti configuration in the solid state. The crystal structure of “HBOCO” revealed the presence of nitroso anion a, BOCO−, and protonated oxime cation b, H2BOCO+, that form a H-bonded dimer in the unit cell. Both molecules adopt planar structures, but different configurations: cis-anti in the molecule a, and trans-anti for b. This is the first reported case of a zwitterionic pair in oximes and the coexistence of the two geometrical cis/trans isomers in the same crystal. All 2-heteroarylcyanoximes form yellow anions upon deprotonation, which exhibit significant negative solvatochromism in solution. Heterogeneous reactions between hot aqueous solutions of Tl2CO3 and solid protonated 2-heteroarylcyanoximes HL afford yellow TlL. The crystal structure of Tl(BTCO) shows the formation of centrosymmetrical dimers, which connect with each other to form a double-stranded one-dimensional coordination polymer. The oxygen atom of the oxime group acts as a bridge between the three different Tl(I) centers. The anion is non-planar and adopts a trans-anti configuration in the complex. The polymeric motif in the complex represents a ladder-type structure. Staggered π–π interactions between benzothiazolyl groups provide additional stabilization of the structure. Both organic ligands and their Tl(I) complexes exhibit strong room temperature blue emission in the solid state.

  合成了一系列五种2-杂芳腈氧肟酸，包括：α-氧肟基-(2-苯并咪唑基)乙腈（HBIHCO）、α-氧肟基-(N-甲基-2-苯并咪唑基)乙腈（HBIMCO）、α-氧肟基-(2-苯并噻唑基)乙腈（HBTCO）和α-氧肟基-(2-喹啉基)乙腈（HQCO）以及它们的单价铊(I) комплексы。采用光谱方法（1H、13C NMR、红外、紫外可见、质谱）和X射线分析对其进行了表征。HBIMCO（作为单水合物）在固态中采用平面反式反式构型。“HBOCO”的晶体结构揭示了存在亚硝基阴离子a（BOCO−）和质子化的氧肟阳离子b（H2BOCO+），它们在单元胞中形成氢键二聚体。这两种分子均采用平面结构，但配置不同：分子a为顺反构型，而b为反式反式构型。这是首次报告在氧肟中发现了两亲离子对，并且同一晶体中共存的两种几何顺/反异构体。所有2-杂芳腈氧肟酸在去质子化后形成黄色阴离子，在溶液中表现出显著的负溶剂色变效应。在Tl2CO3的热水溶液与固态质子化2-杂芳腈氧肟酸HL之间发生的非均相反应生成黄色的TlL。Tl(BTCO)的晶体结构显示形成了中心对称的二聚体，这些二聚体相互连接形成双链一维配位聚合物。氧肟基团的氧原子在三个不同的铊(I)中心之间起桥接作用。该阴离子在复合物中是非平面的，并采用反式反式构型。复杂中的聚合物结构呈现梯子型结构。苯并噻唑基之间错叠的π–π相互作用为结构提供了额外的稳定性。无论是有机配体还是它们的Tl(I)复合物在固态下均表现出强烈的室温蓝色发光。
• Thiadiazolyl-glyoxylonitrile-2-oxime ether derivatives for protecting
  申请人：Ciba-Geigy Corporation

  公开号：US04715883A1

  公开（公告）日：1987-12-29

  A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxide derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts, and the like), as desired, can be treated with these oxide derivatives, which are used as a dressing.

  本发明描述了一种保护耕作植物免受侵蚀性农业化学品的过程，其中使用式为##STR1##的氧化物衍生物作为解毒剂。可以将这些氧化物衍生物作为外衣剂处理耕作植物的耕作区域、耕作植物本身或植物的部分（种子、块茎、茎部等），根据需要进行处理。