1-oximino-1-cyano-3-t-butyl-ketone | 96640-38-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-oximino-1-cyano-3-t-butyl-ketone
• 英文别名: 2-hydroxyimino-4,4-dimethyl-3-oxo-pentanenitrile；pivaloylcyanoxime；α-hydroximido-(2-pivaloyl)acetonitrile；H(PiCO)；2-Hydroxyimino-4,4-dimethyl-3-oxopentanenitrile
• CAS: 96640-38-9
• 化学式: C₇H₁₀N₂O₂
• 分子量: 154.169
• InChiKey: AEFRPKXVCALBMT-UHFFFAOYSA-N

物化性质

• 沸点：
  261.2±23.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-oximino-1-cyano-3-t-butyl-ketone 在 potassium hydroxide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  New non-aggregating bivalent cis-ML2 (M = Pd, Pt; L = pivaloylcyanoxime)

  摘要：

  The 1-oximino-1-cyano-3-t-butyl-ketone (pivaloyl-cyanoxime), HPiCO, and its two new bivalent Pd, Pt complexes of the M(PiCO)(2) composition were synthesized and characterized using UV-Vis, IR spectro-scopic methods, TG/DSC and X-ray analysis. The cyanoxime easily deprotonates upon the addition of a base and forms an anion which exhibits significant solvatochromism: it is pale-yellow in an aqueous solution, but turns pink-red in aprotic DMF with Delta lambda = 79 nm (3670 cm(-1), or 10.3 kcal/M). The ligand HL is an oxime and adopts a trans-anti geometry in a solid state, while in transition metal complexes it is the nitroso anion and has a trans-cis configuration. Both the Pd(PiCO)(2) and Pt(PiCO)(2) obtained are cis-isomers. All compounds characterized by the X-ray analysis crystallize in centrosymmetric space groups. The Pt(PiCO)(2) complex undergoes polymorphic single-crystal-to-single-crystal transition upon cooling: from an orthorhombic crystal system Pnma (#62) at 296 K it becomes monoclinic P2(1)/n (#14) at 100 K. The evaluation of the in vitro cytotoxicity of the new Pd(PiCO)(2) and Pt(PiCO)(2) complexes (which was the secondary, but rather common and traditional goal during the investigations of these Werner-type complexes) was evaluated against the human solid tumor WiDR colon carcinoma. No aggregation of the compounds was detected in the media or in the presence of the cell culture in the 24-wells plates. An assessment of the cytotoxicity of these new complexes indicated that both metal complexes demonstrate a moderate activity at 6-10% of that of anticancer drug [Pt(NH3)(2)Cl-2] (cisplatin) which was used as a positive control. The Pd(PiCO)(2) complex has shown has shown similar - and rather rare for this metal - activity comparable to its Pt-analog, albeit small compared to the conventional anticancer drug. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.10.040
• 作为产物：
  描述：

  新戊酰基乙腈 在 溶剂黄146 、 sodium nitrite 作用下， 生成 1-oximino-1-cyano-3-t-butyl-ketone
  参考文献：
  名称：

  含氰基肟的锌配合物：新戊酰氰基肟-锌体系的结构，光谱和催化研究

  摘要：

  2-羟基亚氨基-4,4-二甲基-3-氧代戊腈（通用缩写HPiCO，新戊酰氰肟）与硫酸锌在水溶液中的反应导致形成两种新的配合物：[Zn（PiCO）{H （微微）2 }（H 2 O）]（我）和四核Zn络合物[锌4（μ 3 -OH）2（微微）6（H 2 O）4 ]（II）。通过元素分析，红外和紫外可见光谱，DSC / TGA研究和X射线分析对这两种配合物进行了表征。在复杂的II，微微- cyanoxime阴离子采用三二种齿配位模式：O型单齿，螯合剂（κ 2），和桥接（η 2）配位。同样，配体代表两种非对映异构体的混合物（顺反和顺顺），它们与锌原子形成五元和六元螯合环，并在一个单位细胞中以0.57-0.43的比例共结晶。有两种不同的晶体的Zn-中心在ASU和两个μ 3 -bridging羟-基团经由反转中心安排优雅的四核配合物的形成。每个Zn原子都有一个配位水分子，并且处于扭曲的八面体环境中。由于

  DOI：

  10.1021/acs.inorgchem.7b01891

文献信息

• 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.
• Zinc Complexes with Cyanoxime: Structural, Spectroscopic, and Catalysis Studies in the Pivaloylcyanoxime–Zn System
  作者：Adedamola A. Opalade、Anirban Karmakar、G. M. D. M. Rúbio、Armando J. L. Pombeiro、Nikolay Gerasimchuk

  DOI：10.1021/acs.inorgchem.7b01891

  日期：2017.11.20

  abbreviation HPiCO, pivaloyl-cyanoxime) with zinc sulfate in an aqueous solution results in the formation of the two new complexes: [Zn(PiCO)H(PiCO)2}(H2O)] (I) and tetranuclear Zn complex [Zn4(μ3–OH)2(PiCO)6 (H2O)4] (II). Both complexes were characterized by elemental analysis, IR– and UV–visible spectra, DSC/TGA studies, and X-ray analysis. In complex II, the PiCO– cyanoxime anion adopts three bidentate

  2-羟基亚氨基-4,4-二甲基-3-氧代戊腈（通用缩写HPiCO，新戊酰氰肟）与硫酸锌在水溶液中的反应导致形成两种新的配合物：[Zn（PiCO）H （微微）2 }（H 2 O）]（我）和四核Zn络合物[锌4（μ 3 -OH）2（微微）6（H 2 O）4 ]（II）。通过元素分析，红外和紫外可见光谱，DSC / TGA研究和X射线分析对这两种配合物进行了表征。在复杂的II，微微- cyanoxime阴离子采用三二种齿配位模式：O型单齿，螯合剂（κ 2），和桥接（η 2）配位。同样，配体代表两种非对映异构体的混合物（顺反和顺顺），它们与锌原子形成五元和六元螯合环，并在一个单位细胞中以0.57-0.43的比例共结晶。有两种不同的晶体的Zn-中心在ASU和两个μ 3 -bridging羟-基团经由反转中心安排优雅的四核配合物的形成。每个Zn原子都有一个配位水分子，并且处于扭曲的八面体环境中。由于
• New non-aggregating bivalent cis-ML2 (M = Pd, Pt; L = pivaloylcyanoxime)
  作者：Alexandra Mann、Nikolay Gerasimchuk、Svitlana Silchenko

  DOI：10.1016/j.ica.2015.10.040

  日期：2016.1

  The 1-oximino-1-cyano-3-t-butyl-ketone (pivaloyl-cyanoxime), HPiCO, and its two new bivalent Pd, Pt complexes of the M(PiCO)(2) composition were synthesized and characterized using UV-Vis, IR spectro-scopic methods, TG/DSC and X-ray analysis. The cyanoxime easily deprotonates upon the addition of a base and forms an anion which exhibits significant solvatochromism: it is pale-yellow in an aqueous solution, but turns pink-red in aprotic DMF with Delta lambda = 79 nm (3670 cm(-1), or 10.3 kcal/M). The ligand HL is an oxime and adopts a trans-anti geometry in a solid state, while in transition metal complexes it is the nitroso anion and has a trans-cis configuration. Both the Pd(PiCO)(2) and Pt(PiCO)(2) obtained are cis-isomers. All compounds characterized by the X-ray analysis crystallize in centrosymmetric space groups. The Pt(PiCO)(2) complex undergoes polymorphic single-crystal-to-single-crystal transition upon cooling: from an orthorhombic crystal system Pnma (#62) at 296 K it becomes monoclinic P2(1)/n (#14) at 100 K. The evaluation of the in vitro cytotoxicity of the new Pd(PiCO)(2) and Pt(PiCO)(2) complexes (which was the secondary, but rather common and traditional goal during the investigations of these Werner-type complexes) was evaluated against the human solid tumor WiDR colon carcinoma. No aggregation of the compounds was detected in the media or in the presence of the cell culture in the 24-wells plates. An assessment of the cytotoxicity of these new complexes indicated that both metal complexes demonstrate a moderate activity at 6-10% of that of anticancer drug [Pt(NH3)(2)Cl-2] (cisplatin) which was used as a positive control. The Pd(PiCO)(2) complex has shown has shown similar - and rather rare for this metal - activity comparable to its Pt-analog, albeit small compared to the conventional anticancer drug. (C) 2015 Elsevier B.V. All rights reserved.