6,7-dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide | 197973-56-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 6,7-dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide
• 英文别名: 6,7-Dichloro-1,4-dihydro-2,3lambda4-benzoxathiine 3-oxide；6,7-dichloro-1,4-dihydro-2,3λ4-benzoxathiine 3-oxide
• CAS: 197973-56-1
• 化学式: C₈H₆Cl₂O₂S
• 分子量: 237.106
• InChiKey: DTVXMFCPKUUWBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide 在 镍 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 叠氮磷酸二苯酯 、 水 、 氢气 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 、 苯 为溶剂， -15.0~100.0 ℃ 、275.79 kPa 条件下， 反应 90.0h， 生成 2,3-diamino-6,7-dichloronaphthalene
  参考文献：
  名称：

  Synthesis of 2,6,7-Trichloro-1-(β-d-ribofuranosyl)naphtho[2,3-d]imidazole:  A Linear Dimensional Analogue of the Antiviral Agent TCRB

  摘要：

  Human cytomegalovirus (HCMV) remains a significant clinical problem in neonates and immunocompromised individuals such as those undergoing transplantation as well as individuals with acquired immune deficiency syndrome (AIDS). Recently in our laboratory, 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB, 1a) and 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BDCRB, 1b) were found to have better activities in cell culture studies against HCMV than the clinically used agents ganciclovir and foscarnet. These benzimidazole compounds appear to act by a unique mechanism. However, as the biological target of TCRB and BDCRB has not been completely identified, 2,6,7-trichloro-1-(beta-D-ribofuranosyl)naphthol[2,3-d]imidazole (2) was designed as a linear dimensional analogue of TCRB for a study on the spatial limitation of the binding site in the target enzyme. In the synthesis, a convenient route was developed for the synthesis of 2-substituted 6,7-dichloronaphtho[2,3-d]imidazoles involving a Diels-Alder reaction of 4,5-dichloro-o-quinodimethane (8) as the key step. 6,7-Dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide (15) was found to be an ideal precursor for the generation of the elusive intermediate 8. The ribosylation of 6,7-dichloronaphtho[2,3-d]imidazoles was influenced by the functional group at the 2-position and 6,7-dichloro-2-methylthionaphtho[2,3-d]imidazole (3c) was found to smoothly undergo ribosylation. The 2-methylthio group of the unprotected nucleoside 25 was converted into a chloro group under mild conditions to give nucleoside 2 in high yield.

  DOI：

  10.1021/jo971152o
• 作为产物：
  描述：

  1,2-二溴甲基-4,5-二氯苯 在 四丁基溴化铵 、 rongalite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6,7-dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide
  参考文献：
  名称：

  Synthesis of 2,6,7-Trichloro-1-(β-d-ribofuranosyl)naphtho[2,3-d]imidazole:  A Linear Dimensional Analogue of the Antiviral Agent TCRB

  摘要：

  Human cytomegalovirus (HCMV) remains a significant clinical problem in neonates and immunocompromised individuals such as those undergoing transplantation as well as individuals with acquired immune deficiency syndrome (AIDS). Recently in our laboratory, 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB, 1a) and 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BDCRB, 1b) were found to have better activities in cell culture studies against HCMV than the clinically used agents ganciclovir and foscarnet. These benzimidazole compounds appear to act by a unique mechanism. However, as the biological target of TCRB and BDCRB has not been completely identified, 2,6,7-trichloro-1-(beta-D-ribofuranosyl)naphthol[2,3-d]imidazole (2) was designed as a linear dimensional analogue of TCRB for a study on the spatial limitation of the binding site in the target enzyme. In the synthesis, a convenient route was developed for the synthesis of 2-substituted 6,7-dichloronaphtho[2,3-d]imidazoles involving a Diels-Alder reaction of 4,5-dichloro-o-quinodimethane (8) as the key step. 6,7-Dichloro-1,4-dihydro-2,3-benzoxathiin 3-oxide (15) was found to be an ideal precursor for the generation of the elusive intermediate 8. The ribosylation of 6,7-dichloronaphtho[2,3-d]imidazoles was influenced by the functional group at the 2-position and 6,7-dichloro-2-methylthionaphtho[2,3-d]imidazole (3c) was found to smoothly undergo ribosylation. The 2-methylthio group of the unprotected nucleoside 25 was converted into a chloro group under mild conditions to give nucleoside 2 in high yield.

  DOI：

  10.1021/jo971152o