3-chloromethyl-6-methyl-6H-indolo[2,3-b]quinoxaline | 917077-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-chloromethyl-6-methyl-6H-indolo[2,3-b]quinoxaline
• CAS: 917077-16-8
• 化学式: C₁₆H₁₂ClN₃
• 分子量: 281.744
• InChiKey: HTHADEFZSCMDBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-chloromethyl-6-methyl-6H-indolo[2,3-b]quinoxaline 在 氢氧化钾 、 二异丙基铵盐四氮唑 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 84.0h， 生成 Diisopropyl-phosphoramidous acid (S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(6-methyl-6H-indolo[2,3-b]quinoxalin-3-ylmethoxy)-propyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

  摘要：

  6H-Indolo[2,3-b]quinoxaline was studied as a covalently bound heteroaromatic intercalator. Six monomers were synthesized and incorporated into DNA oligonucleotides. Through a study of linker length dependence it was concluded that the linker between the oligo and the intercalator must consist of at least five C atoms in order to stabilize a DNA duplex. An intercalator with a 2 '-deoxy-D-riboside linker to the oligo could also stabilize a DNA/RNA duplex, while (S)-4-(6-methylindolo[2,3-b]quinoxalin-3-ylmethoxy)-butane-1,2-diol was able to stabilize both DNA/DNA, DNA/RNA and a DNA/LNA duplex. Mismatch studies revealed a huge sensitivity to the C-C mismatch at the 5'-site of the intercalator. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.017
• 作为产物：
  描述：

  (6-methyl-6H-indolo[2,3-b]quinoxalin-3-yl)methanol 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到3-chloromethyl-6-methyl-6H-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

  摘要：

  6H-Indolo[2,3-b]quinoxaline was studied as a covalently bound heteroaromatic intercalator. Six monomers were synthesized and incorporated into DNA oligonucleotides. Through a study of linker length dependence it was concluded that the linker between the oligo and the intercalator must consist of at least five C atoms in order to stabilize a DNA duplex. An intercalator with a 2 '-deoxy-D-riboside linker to the oligo could also stabilize a DNA/RNA duplex, while (S)-4-(6-methylindolo[2,3-b]quinoxalin-3-ylmethoxy)-butane-1,2-diol was able to stabilize both DNA/DNA, DNA/RNA and a DNA/LNA duplex. Mismatch studies revealed a huge sensitivity to the C-C mismatch at the 5'-site of the intercalator. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.017