(+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl]{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone | 516509-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl]{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone
• 英文别名: [2-[3-[tert-butyl(diphenyl)silyl]oxybutyl]-1-benzofuran-3-yl]-[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone
• CAS: 516509-86-7
• 化学式: C₄₁H₄₇I₂NO₄Si
• 分子量: 899.723
• InChiKey: NBHHGURWKPJZBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  778.0±60.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.49
• 重原子数：
  49.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  51.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl]{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 38.0h， 以37%的产率得到(+/-)-{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}[2-(3-hydroxybutyl)benzofuran-3-yl]methanone
  参考文献：
  名称：

  摘要：

  The metabolism of the potent antiarrythmic drug amiodarone (AMI 1) has yet not been fully investigated. Recently, in vitro experiments revealed that in rabbit-liver microsomes, AMI (1) and its main metabolite MDEA (2) were biotransformed to the hydroxylated derivatives T-OH-AMI (3) and 3'-OH-MDEA (4). respectively. To establish the chemical structure of 3 and 4, we developed a total synthesis of these two metabolites of AMI (1). H-1- and C-13-NMR Signal assignment from HSQC and HMBC 2D NMR data of synthesized 4 showed that the proposed structure of metabolite 4 is correct. Even the structure of 3 was found to be correct by comparing its HPLC/MS-MS/MS with the data described earlier.

  DOI：

  10.1002/1522-2675(200209)85:9<2990::aid-hlca2990>3.0.co;2-r
• 作为产物：
  描述：

  methyl 4-hydroxypentanoate 在 四氯化锡 、 sodium iodide 咪唑 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium hydroxide 、 碘 、 sodium acetate 、 potassium carbonate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 乙硫醇钠 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 90.0h， 生成 (+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl]{4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone
  参考文献：
  名称：

  摘要：

  The metabolism of the potent antiarrythmic drug amiodarone (AMI 1) has yet not been fully investigated. Recently, in vitro experiments revealed that in rabbit-liver microsomes, AMI (1) and its main metabolite MDEA (2) were biotransformed to the hydroxylated derivatives T-OH-AMI (3) and 3'-OH-MDEA (4). respectively. To establish the chemical structure of 3 and 4, we developed a total synthesis of these two metabolites of AMI (1). H-1- and C-13-NMR Signal assignment from HSQC and HMBC 2D NMR data of synthesized 4 showed that the proposed structure of metabolite 4 is correct. Even the structure of 3 was found to be correct by comparing its HPLC/MS-MS/MS with the data described earlier.

  DOI：

  10.1002/1522-2675(200209)85:9<2990::aid-hlca2990>3.0.co;2-r