4-(4-chloro-7-nitrobenzo[b]selenophen-2-yl)morpholine | 1427505-13-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-(4-chloro-7-nitrobenzo[b]selenophen-2-yl)morpholine
• CAS: 1427505-13-2
• 化学式: C₁₂H₁₁ClN₂O₃Se
• 分子量: 345.644
• InChiKey: HIPHDZOFCYSJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氯-5-硝基苯乙酮 在 selenium(IV) oxide 、 potassium permanganate 、 sodium acetate 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 11.0h， 生成 4-(4-chloro-7-nitrobenzo[b]selenophen-2-yl)morpholine
  参考文献：
  名称：

  A Novel Synthesis of Benzo[b]selenophenes via Regioselective Intramolecular Transformation of 4-(3-Nitroaryl)-1,2,3-selenadiazoles

  摘要：

  Base-promoted transformation of 4-(3-nitroaryl)-1,2,3-selenadiazoles via intermediate formation of eneselenolates followed by 5-exo-trig cyclization Is reported. The regiochemistry of the intramolecular cyclization is condition-dependent. In the presence of an oxidant, the oxidative nucleophilic substitution of the hydrogen (ONSH, SNArH) pathway, by oxidative aromatization of the rapidly formed sigma(H)-adduct, takes place. In the absence of oxidant, the reaction proceeds via intermediate formation of the sigma(Cl)-adduct, following nucleophilic aromatic substitution of the halogen (SNArCl) pathway.

  DOI：

  10.1021/ol400547n

文献信息

• A Novel Synthesis of Benzo[<i>b</i>]selenophenes via Regioselective Intramolecular Transformation of 4-(3-Nitroaryl)-1,2,3-selenadiazoles
  作者：Anna G. Lyapunova、Mikhail L. Petrov、Dmitry A. Androsov

  DOI：10.1021/ol400547n

  日期：2013.4.5

  Base-promoted transformation of 4-(3-nitroaryl)-1,2,3-selenadiazoles via intermediate formation of eneselenolates followed by 5-exo-trig cyclization Is reported. The regiochemistry of the intramolecular cyclization is condition-dependent. In the presence of an oxidant, the oxidative nucleophilic substitution of the hydrogen (ONSH, SNArH) pathway, by oxidative aromatization of the rapidly formed sigma(H)-adduct, takes place. In the absence of oxidant, the reaction proceeds via intermediate formation of the sigma(Cl)-adduct, following nucleophilic aromatic substitution of the halogen (SNArCl) pathway.