(+/-)-4-{[(tert-butyl)diphenylsilyl]oxy}pentanoic acid | 87305-75-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (+/-)-4-{[(tert-butyl)diphenylsilyl]oxy}pentanoic acid
• 英文别名: 4-(tert-butyldiphenylsiloxy)pentanoic acid；4-[Tert-butyl(diphenyl)silyl]oxypentanoic acid
• CAS: 87305-75-7
• 化学式: C₂₁H₂₈O₃Si
• 分子量: 356.537
• InChiKey: YRTGHVQPLYFLGA-UHFFFAOYSA-N

物化性质

• 沸点：
  446.7±37.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-{[(tert-butyl)diphenylsilyl]oxy}pentanoic acid 在 四氯化锡 4-二甲氨基吡啶 、 sodium hydroxide 、 碘 、 sodium acetate 、 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 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 (+/-)-[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-hydroxypentanoate 在 咪唑 、 4-二甲氨基吡啶 、 氢氧化钾 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 (+/-)-4-{[(tert-butyl)diphenylsilyl]oxy}pentanoic acid
  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

文献信息

• Synthesis of a pyrenophorin precursor, 7-hydroxy-4-oxo-2-octenoic acid by the direct palladium catalyzed coupling of an acrylic tin reagent with an acid chloride
  作者：Jeff W. Labadie、J.K. Stille

  DOI：10.1016/s0040-4039(00)88321-5

  日期：1983.1

  A palladium catalyzed coupling reaction of an organotin reagent bearing acrylate functionality with an acid chloride serves as a method to introduce both a ketone and an acrylate functionality into a carbon framework; thus the coupling reaction of 4-t-butyldiphenylsiloxypentanoyl chloride with benzyl 3-tributylstannylacrylate gave a 71% yield of benzyl 7-t-butyldiphenylsiloxy-4-oxo-2-octenoate, which

  具有丙烯酸酯官能度的有机锡试剂与酰基氯的钯催化的偶联反应用作将酮和丙烯酸酯官能度两者引入碳骨架的方法。因此，4-叔丁基二苯基甲硅烷氧基戊酰氯与丙烯酸苄基3-三丁基锡烷基酯的偶合反应得到71％的苄基7-叔丁基二苯基甲硅烷氧基-4-氧代-2-辛烯酸酯，将其转化为7-羟基-4-缩酮氧代-2-辛烯酸，大环内酯类抗生素吡喃蛋白的前体。
• Synthetic utility of the palladium-catalyzed coupling reaction of acid chlorides with organotins
  作者：Jeff W. Labadie、David Tueting、J. K. Stille

  DOI：10.1021/jo00172a038

  日期：1983.12