4-[1-Naphthalen-1-yl-meth-(Z)-ylidene]-2,5-bis-trimethylsilanyloxy-4H-imidazole | 151559-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[1-Naphthalen-1-yl-meth-(Z)-ylidene]-2,5-bis-trimethylsilanyloxy-4H-imidazole
• CAS: 151559-51-2
• 化学式: C₂₀H₂₆N₂O₂Si₂
• 分子量: 382.61
• InChiKey: UGENJPMOUXCDMO-JXAWBTAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[1-Naphthalen-1-yl-meth-(Z)-ylidene]-2,5-bis-trimethylsilanyloxy-4H-imidazole 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 72.0h， 生成 7-[(S)-3,4-dihydroxybutyl]-7H-7a,9-diazacyclopenta[b]phenanthrene-8,10-dione
  参考文献：
  名称：

  Synthesis and DNA Binding Properties of a New Benzo[f]Imidazo[1,5b]-Isoquinoline-Butan-1,2-Diol Derivative

  摘要：

  A benzo[f]imidazo[1,5b]-isoquinoline derivative 4 with a 1,2-butandiol linker was prepared by reaction of a trimethylsilylated 5-naphthylidenehydantoin 3 with a 2,3-dideoxy-D-glyceropentafuranoside 2 in 22% yield. After deprotection, the resulting compound 5 was converted to a DMT protected phosphoramidite building block 7 for standard DNA synthesis. DNA/DNA, DNA/RNA duplexes with 5 inserted as bulges were destabilized, except when the new amidite was used for the synthesis of a zipping duplex.

  DOI：

  10.1080/15257770600918524
• 作为产物：
  描述：

  1-萘甲醛 在 哌啶 、 硫酸氢铵 作用下， 生成 4-[1-Naphthalen-1-yl-meth-(Z)-ylidene]-2,5-bis-trimethylsilanyloxy-4H-imidazole
  参考文献：
  名称：

  Hydantoin analogs of thymidine

  摘要：

  Hydantoin nucleosides were synthesized from a protected methyl 2-deoXy-D-ribofuranoside in a Friedel-Crafts catalyzed silyl-Hilbert-Johnson reaction as modified by Vorbruggen. Atypical byproducts are accounted for by assuming the initial step being a ring opening of the sugar to give an acyclic glycos-1-yl cation.

  DOI：

  10.1021/jo00074a028