(Z)-2-(hydroxyimino)-2-(4-nitrophenyl)acetonitrile | 130691-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-(hydroxyimino)-2-(4-nitrophenyl)acetonitrile
• 英文别名: hydroxyimino-(4-nitro-phenyl)-acetonitrile；Hydroxyimino-(4-nitro-phenyl)-essigsaeure-nitril；Hydroxyimino-(4-nitro-phenyl)-acetonitril；(2Z)-2-hydroxyimino-2-(4-nitrophenyl)acetonitrile
• CAS: 130691-14-4
• 化学式: C₈H₅N₃O₃
• 分子量: 191.146
• InChiKey: VSICAJJUUBRBQO-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.52
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-(hydroxyimino)-2-(4-nitrophenyl)acetonitrile 在 盐酸 、 盐酸羟胺 、 sodium acetate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 126.58h， 生成 3-chloro-4-(4'-nitrophenyl)-1,2,5-oxadiazole
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

  摘要：

  A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 +/- 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 +/- 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.013
• 作为产物：
  描述：

  对硝基苯甲醛 在 N-氯代丁二酰亚胺 、 盐酸羟胺 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 56.0h， 生成 (Z)-2-(hydroxyimino)-2-(4-nitrophenyl)acetonitrile
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides

  摘要：

  A number of structural analogues of the known toxicant para-aminopropiophenone (PAPP) have been prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed for alkyl analogues of PAPP (aminophenones 1-20; compound 6 metHb% = 74.1 +/- 2). Besides lipophilicity, this structural sub-class suggested there were certain structural requirements for activity, with both branched (10-16) and cyclic (17-20) alkyl analogues exhibiting inferior in vitro metHb induction. Of the four candidates (compounds 4, 6, 13 and 23) evaluated in vivo, 4 exhibited the greatest toxicity. In parallel, aminophenone bioisosteres, including oximes 30-32, sulfoxide 33, sulfone 34 and sulfonamides 35-36, were found to be inferior metHb inducers to lead ketone 4. Closer examination of Hammett substituent constants suggests that a particular combination of the field and resonance parameters may be significant with respect to the redox mechanisms behind PAPPs metHb toxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.046

文献信息

• Synthesis, larvicidal activity, and SAR studies of new benzoylphenylureas containing oxime ether and oxime ester group
  作者：Ranfeng Sun、Yongqiang Li、Maoyun Lü、Lixia Xiong、Qingmin Wang

  DOI：10.1016/j.bmcl.2010.04.144

  日期：2010.8

  A series of new structural benzoylphenylureas (BPUs) containing oxime ether and oxime ester group were designed and synthesized. The larvicidal activities against Oriental armyworm and mosquito of these benzoylphenylureas were evaluated and the result of bioassay displayed specific structure–activity relationship (SAR). Most of the compounds exhibited excellent larvicidal activities against Oriental

  设计并合成了一系列含有肟醚和肟酯基的新型结构苯甲酰基苯基脲（BPU）。评估了这些苯甲酰基苯基脲对东方粘虫和蚊子的杀幼虫活性，生物测定的结果显示出特定的构效关系（SAR）。大多数化合物对东方粘虫和蚊子均表现出优异的杀幼虫活性。有趣的是，一些化合物对小菜蛾，甜菜夜蛾和玉米bore表现出不同的结构-活性关系，尽管三种经过测试的昆虫都属于同一昆虫纲。
• DE MUNNO A.; BERTINI V.; MENCONI A.; DENTI G., ATTI SOC. SCI. NATUR. MEM., 1974(1975), A81, 334-342
  作者：DE MUNNO A.、 BERTINI V.、 MENCONI A.、 DENTI G.

  DOI：——

  日期：——
• BOYER, JOSEPH H.;MANIMARAN, THANKIAVELU;RAMAKRISHNAN, VAYALAKKAVOOR T., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 10, 2163-2169
  作者：BOYER, JOSEPH H.、MANIMARAN, THANKIAVELU、RAMAKRISHNAN, VAYALAKKAVOOR T.

  DOI：——

  日期：——