Diethyl N-methyl-10H-<1>benzoselenopheno<3,2-b>indole-2,7-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Diethyl N-methyl-10H-<1>benzoselenopheno<3,2-b>indole-2,7-dicarboxylate
• 英文别名: Diethyl 10-methyl-[1]benzoselenolo[3,2-b]indole-2,7-dicarboxylate
• 化学式: C₂₁H₁₉NO₄Se
• 分子量: 428.346
• InChiKey: MQZAQMLSPIKGJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-chloromethyl-3-nitrobenzoic acid 在 盐酸 、 氯化亚砜 、 溴 、 sodium ethanolate 、 sodium acetate 、 potassium hydride 、 sodium disulfide 、 sodium nitrite 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 21.75h， 生成 Diethyl N-methyl-10H-<1>benzoselenopheno<3,2-b>indole-2,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and properties of diethyl 5,10-dihetera-5,10-dihydroindeno[2,1-a]indene-2,7-dicarboxylates

  摘要：

  A series of six heterocyclic diesters lb-6b containing all combinations of nitrogen, sulfur, and selenium has been prepared from a common precursor, diethyl 2,2'-dinitrostilbene-4,4'-dicarboxylate. Electrochemical analysis showed oxidation potential increases in the order N < Se < S, and the same trend was observed for maxima of UV absorbance. Electrochemical oxidation of indoloindole lb (but not the other members of the series) generates a persistent radical cation whose properties were investigated. Diesters containing sulfur and selenium (but not nitrogen) form S(A) liquid crystals. A new synthetic method leading to the indolo[1,2-b]indazole ring system has been found.

  DOI：

  10.1021/jo00071a034

文献信息

• Synthesis and properties of diethyl 5,10-dihetera-5,10-dihydroindeno[2,1-a]indene-2,7-dicarboxylates
  作者：Piotr Kaszynski、Dennis A. Dougherty

  DOI：10.1021/jo00071a034

  日期：1993.9

  A series of six heterocyclic diesters lb-6b containing all combinations of nitrogen, sulfur, and selenium has been prepared from a common precursor, diethyl 2,2'-dinitrostilbene-4,4'-dicarboxylate. Electrochemical analysis showed oxidation potential increases in the order N < Se < S, and the same trend was observed for maxima of UV absorbance. Electrochemical oxidation of indoloindole lb (but not the other members of the series) generates a persistent radical cation whose properties were investigated. Diesters containing sulfur and selenium (but not nitrogen) form S(A) liquid crystals. A new synthetic method leading to the indolo[1,2-b]indazole ring system has been found.