2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho<2,3-d>imidazol-4,9-dione | 156904-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho<2,3-d>imidazol-4,9-dione
• 英文别名: 2-(Chloromethyl)-3-methylbenzo[f]benzimidazole-4,9-dione
• CAS: 156904-71-1
• 化学式: C₁₃H₉ClN₂O₂
• 分子量: 260.68
• InChiKey: BWSIJNMYCWTXIH-UHFFFAOYSA-N

物化性质

• 沸点：
  495.8±33.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho<2,3-d>imidazol-4,9-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione
  参考文献：
  名称：

  Preparation and in vitro antiprotozoan activity of new naphthoimidazolediones

  摘要：

  The original compound bearing the coplanar quinone and imidazole systems, 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d]imidazol-4,9-dione reacted with various nitronate anions to afford, in moderate to good yields, new naphthoimidazolediones bearing a trisubstituted ethylenic double bond at the 2-position. These compounds were evaluated as potential antiprotozoan agents. Some derivatives were found to have a significant activity, but the naphthoquinone was found to be a less efficient pharmacophore than the nitro group.

  DOI：

  10.1016/s0223-5234(97)84015-9
• 作为产物：
  描述：

  2-氨基-3-氯-1,4-萘醌 在 乙酰氯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 13.5h， 生成 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho<2,3-d>imidazol-4,9-dione
  参考文献：
  名称：

  涉及稠合的醌咪唑还原性烷基化剂的首次电子转移C-烷基化

  摘要：

  通过S RN显示2-氯甲基-4,9-二氢-1-甲基-1H-萘并[2,3-d]咪唑-4,9-二酮与2-硝基丙烷阴离子的C-烷基化反应已进行。1机制。该机理被双氧，对二硝基苯，氯化铜和TEMPO的抑制作用所证实。

  DOI：

  10.1016/s0040-4039(00)76892-4

文献信息

• First electron transfer C-alkylation involving a fused quinoneimidazole reductive alkylating agent
  作者：Patrice Vanelle、Santa Donini、José Maldonado、Jean-François Sabuco、Michel P. Crozet

  DOI：10.1016/s0040-4039(00)76892-4

  日期：1994.5

  The C-alkylation reaction of 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d]imidazol-4,9-dione by 2-nitropropane anion is shown to proceed by the SRN1 mechanism. This mechanism is confirmed by the inhibitory effects of dioxygen, p-dinitrobenzene, cupric chloride and TEMPO.

  通过S RN显示2-氯甲基-4,9-二氢-1-甲基-1H-萘并[2,3-d]咪唑-4,9-二酮与2-硝基丙烷阴离子的C-烷基化反应已进行。1机制。该机理被双氧，对二硝基苯，氯化铜和TEMPO的抑制作用所证实。
• Vanelle Patrice, Donini Santa, Maldonado Jose, Sabuco Jean-Francois, Croz+, Tetrahedron Lett, 35 (1994) N 20, S 3305-3308
  作者：Vanelle Patrice, Donini Santa, Maldonado Jose, Sabuco Jean-Francois, Croz+

  DOI：——

  日期：——
• Preparation and in vitro antiprotozoan activity of new naphthoimidazolediones
  作者：P Vanelle、S Donini、J Maldonado、M.P. Crozet、F Delmas、M Gasquet、P Timon-David

  DOI：10.1016/s0223-5234(97)84015-9

  日期：1997.6

  The original compound bearing the coplanar quinone and imidazole systems, 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d]imidazol-4,9-dione reacted with various nitronate anions to afford, in moderate to good yields, new naphthoimidazolediones bearing a trisubstituted ethylenic double bond at the 2-position. These compounds were evaluated as potential antiprotozoan agents. Some derivatives were found to have a significant activity, but the naphthoquinone was found to be a less efficient pharmacophore than the nitro group.