N-hydroxy-3,5-dichloro-2,4,6-trimethoxybenzenecarboximidoyl chloride | 1399860-83-3

• 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-hydroxy-3,5-dichloro-2,4,6-trimethoxybenzenecarboximidoyl chloride
• CAS: 1399860-83-3
• 化学式: C₁₀H₁₀Cl₃NO₄
• 分子量: 314.553
• InChiKey: SIUGIIQLUPFLMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.28
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-hydroxy-3,5-dichloro-2,4,6-trimethoxybenzenecarboximidoyl chloride 、 美雌醇 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以98%的产率得到3-methoxy-17α-[3'-(3",5"-dichloro-2",4",6"-trimethoxy)phenylisoxazol-5'-yl]estra-1,3,5(10)-trien-17β-ol
  参考文献：
  名称：

  Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series

  摘要：

  Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17 alpha-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecular ring-closures and leading exclusively to 3,5-disubstituted isoxazoles. The yields of the cycloadducts, however, were influenced by the substituents on the aromatic moiety of the 1,3-dipoles. Moreover, dehydration of the primary products resulted in the corresponding Delta(16.17) exo-heterocyclic derivatives. All the synthesized compounds were subjected to in vitro pharmacological studies of their antiproliferative effects relative to three human malignant cell lines (HeLa, MCF7 and A2780). (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.003
• 作为产物：
  描述：

  3,5-dichloro-2,4,6-trimethoxybenzaldehyde oxime 在 N-氯代丁二酰亚胺 作用下， 生成 N-hydroxy-3,5-dichloro-2,4,6-trimethoxybenzenecarboximidoyl chloride
  参考文献：
  名称：

  Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series

  摘要：

  Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17 alpha-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecular ring-closures and leading exclusively to 3,5-disubstituted isoxazoles. The yields of the cycloadducts, however, were influenced by the substituents on the aromatic moiety of the 1,3-dipoles. Moreover, dehydration of the primary products resulted in the corresponding Delta(16.17) exo-heterocyclic derivatives. All the synthesized compounds were subjected to in vitro pharmacological studies of their antiproliferative effects relative to three human malignant cell lines (HeLa, MCF7 and A2780). (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.003