N-[2-chloro-1-(4-methylphenyl)ethylidene]hydroxylamine | 139620-84-1

• 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: N-[2-chloro-1-(4-methylphenyl)ethylidene]hydroxylamine
• CAS: 139620-84-1
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: JCTVAXHWKZYKBM-UHFFFAOYSA-N

物化性质

• 沸点：
  295.3±33.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-chloro-1-(4-methylphenyl)ethylidene]hydroxylamine 在 sodium carbonate 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 4.0h， 生成 1-(p-chlorophenyl)-2--4-(p-tolyl)imidazole
  参考文献：
  名称：

  Sharma, Arun K.; Hundal, Geeta; Obrai, Sangeeta, Journal of the Chemical Society. Perkin transactions I, 1999, # 5, p. 615 - 619

  摘要：

  DOI：

文献信息

• Silver-mediated radical cyclization: construction of Δ2-isoxazolines from α-halo ketoximes and 1,3-dicarbonyl compounds
  作者：Yan-Yun Liu、Xu-Heng Yang、Ji Yang、Ren-Jie Song、Jin-Heng Li

  DOI：10.1039/c4cc02084g

  日期：——

  A novel route to Delta(2)-isoxazolines is presented via silver-mediated radical cyclization of alpha-halo ketoximes with 1,3-dicarbonyl compounds. This method is performed using a radical strategy, and represents a new example of silver-initiated generation of oxime radicals for the formation of the C(sp(3))-O bonds.

  通过银介导的含1,3-二羰基化合物的α-卤代酮肟的自由基环化反应，提出了一种通往Delta（2）-异恶唑啉的新途径。此方法是使用自由基策略执行的，代表了由银引发的肟自由基生成C（sp（3））-O键的新示例。
• Synthesis of 6-alkoxy-3-aryl-6-trimethylsilyloxy-5,6-dihydro-4H-1,2-oxazines and their acid-catalysed hydrolysis leading to 3-aryl-5,6-dihydro-4H-1,2-oxazin-6-ones and/or 4-aryl-4-(hydroxyimino)butyric acid esters
  作者：Shigeo Tanimoto、Hideshi Matsumoto、Makoto Hojo、Akio Toshimitsu

  DOI：10.1039/p19910003153

  日期：——

  α-nitrosostyrene and its ring-substituted derivatives, which are generated by the reaction of α-chloroacetophenone oxime and its ring-substituted derivatives with K2CO3 in tetrahydrofuran, with ketene trimethylsilyl acetals proceeds to afford 6-alkoxy-3-aryl-6-trimethylsilyloxy-5,6-dihydro-4H-1,2-oxazines. These oxazines are susceptible to hydrochloric acid-catalysed hydrolysis affording 3-aryl -5,6-dihydro-4H-1

  由α-氯苯乙酮肟及其环取代的衍生物与K 2 CO 3在四氢呋喃中的反应生成的α-亚硝基苯乙烯及其环取代的衍生物与乙烯酮三甲基甲硅烷基乙缩醛的环加成反应得到6-烷氧基-3 -芳基-6-三甲基甲硅烷氧基-5,6-二氢-4 H -1,2-恶嗪。这些恶嗪易受盐酸催化的水解，得到3-芳基-5,6-二氢-4 H -1,2-恶嗪6-1和/或4-芳基-4-（羟基亚氨基）丁酸酯。
• Synthesis of functionalised cyclic nitrones via regioselective and unusual [3 + 2] cycloadditions of α-nitrosostyrenes with 1,3-diazabuta-1,3-dienes and imines
  作者：Arun K. Sharma、Sujit N. Mazumdar、Mohinder P. Mahajan

  DOI：10.1039/a702254i

  日期：——

  The α-nitrosostyrenes 2, generated in situ from α-halogeno oximes, undergo regioselective [3 + 2] cycloaddition with 1,3-diazabuta-1,3-dienes 1 and 5 leading to the cyclic nitrones 3 and 6, respectively. Similarly, the cyclic nitrones 12 are also formed in reactions of 2 with the trisubstituted amidines 11. Thermolysis of the nitrones 3 and 12d–f gives imidazole derivatives 13. The nitrones 6, on the other hand, on thermolysis under similar conditions, give the amidine derivatives 17. Interestingly, the treatment of both 3 and 6 with NaBH4 in methanol and the reactions of 2 with N-arylbenzamidines also yield the imidazole derivatives 13.

  由 α-卤代肟原位生成的 α-亚硝基苯乙烯 2，与 1,3-diazabuta-1,3-二烯 1 和 5 进行区域选择性 [3+2] 环加成，生成环状硝酮 3 和 6，分别。类似地，环状硝酮 12 也在 2 与三取代脒 11 的反应中形成。硝酮 3 和 12d-f 的热解得到咪唑衍生物 13。另一方面，硝酮 6 在类似条件下热解，得到脒衍生物 17。有趣的是，用 NaBH4 在甲醇中处理 3 和 6，以及 2 与 N-芳基苯甲脒反应也得到咪唑衍生物 13。
• Sharma, Arun K.; Mahajan, Mohinder P., Heterocycles, 1995, vol. 40, # 2, p. 787 - 800
  作者：Sharma, Arun K.、Mahajan, Mohinder P.

  DOI：——

  日期：——
• Reactions of Monohalomethyl Aryl Ketoximes with Tetrasulfur Tetranitride: Much Improved Synthesis of 3-Aryl-1,2,5-thiadiazoles
  作者：Kyongtae Kim、Jaeeock Cho

  DOI：10.3987/com-94-6755

  日期：——

  Reactions of chloromethyl aryl ketoximes (1, X = Cl) with tetrasulfur tetranitride in p-dioxane at reflux for 4 h afforded 3-aryl-1,2,5-thiadiazoles (2) in 37-92% yields, whereas those of bromo analogs under the same conditions gave 2 and 3-aryl-4-bromo-1,2,5-thiadiazoles (3) in 48-81% and 17-31% yields, respectively. However, the compounds (3) were not formed in the presence of pyridine. Alpha-nitrosostyrene and its ring-substituted derivatives (4) are proposed as intermediates for the formations of 2.