(+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl](4-hydroxyphenyl)methanone | 516509-29-8

• 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-hydroxyphenyl)methanone
• 英文别名: [2-[3-[tert-butyl(diphenyl)silyl]oxybutyl]-1-benzofuran-3-yl]-(4-hydroxyphenyl)methanone
• CAS: 516509-29-8
• 化学式: C₃₅H₃₆O₄Si
• 分子量: 548.754
• InChiKey: CUIOTPADEOGHEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.27
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl](4-hydroxyphenyl)methanone 在 sodium hydroxide 、 碘 、 sodium acetate 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 以99%的产率得到(+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl](4-hydroxy-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
• 作为产物：
  描述：

  (+/-)-methyl 4-{[(tert-butyl)diphenylsilyl]oxy}pentanoate 在 四氯化锡 4-二甲氨基吡啶 、 氢氧化钾 、 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 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (+/-)-[2-(3-{[(tert-butyl)diphenylsilyl]oxy}butyl)benzofuran-3-yl](4-hydroxyphenyl)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