(4-fluoro-5-iodo-indol-1-yl)-triisopropylsilane | 1240113-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (4-fluoro-5-iodo-indol-1-yl)-triisopropylsilane
• 英文别名: 4-Fluoro-5-iodo-1-(triisopropylsilyl)-1H-indole；(4-fluoro-5-iodoindol-1-yl)-tri(propan-2-yl)silane
• CAS: 1240113-38-5
• 化学式: C₁₇H₂₅FINSi
• 分子量: 417.381
• InChiKey: WZAIPMWEVNLWOE-UHFFFAOYSA-N

物化性质

• 沸点：
  360.2±35.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-fluoro-5-iodo-indol-1-yl)-triisopropylsilane 在 sodium tetrahydroborate 、 四丁基氟化铵 、 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 4.58h， 生成 (4-fluoro-5-iodo-1-tosyl-1H-indol-3-yl)methanol
  参考文献：
  名称：

  Radiosynthesis of 4-[ 18 F]fluoro- l -tryptophan by isotopic exchange on carbonyl-activated precursors

  摘要：

  Several F-18-labeled aromatic amino acids have been developed primarily for tumor imaging with positron-emission-tomography (PET). Also, F-18-labeled tryptophan derivatives were synthesized by electrophilic F-18-fluorination or by introducing a [F-18]fluoroalkyl group. Here, a 3-step method for a nucleophilic radiosynthesis of 4-[1(8F)]fluoro-L-tryptophan was developed. A carbonyl activated precursor containing a chiral amino acid building block was radiofluorinated by isotopic exchange, followed by removal of the activating formyl group by reductive decarbonylation and subsequent cleavage of the building block under acidic conditions. The title compound was obtained within 100 min with a radiochemical yield of about 13%, a molar activity of >70 MBq/mmol and an enantiomeric excess of >99%. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.073
• 作为产物：
  描述：

  三异丙基氯硅烷 在 正丁基锂 、 五甲基二乙烯三胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 (4-fluoro-5-iodo-indol-1-yl)-triisopropylsilane
  参考文献：
  名称：

  Radiosynthesis of 4-[ 18 F]fluoro- l -tryptophan by isotopic exchange on carbonyl-activated precursors

  摘要：

  Several F-18-labeled aromatic amino acids have been developed primarily for tumor imaging with positron-emission-tomography (PET). Also, F-18-labeled tryptophan derivatives were synthesized by electrophilic F-18-fluorination or by introducing a [F-18]fluoroalkyl group. Here, a 3-step method for a nucleophilic radiosynthesis of 4-[1(8F)]fluoro-L-tryptophan was developed. A carbonyl activated precursor containing a chiral amino acid building block was radiofluorinated by isotopic exchange, followed by removal of the activating formyl group by reductive decarbonylation and subsequent cleavage of the building block under acidic conditions. The title compound was obtained within 100 min with a radiochemical yield of about 13%, a molar activity of >70 MBq/mmol and an enantiomeric excess of >99%. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.073

文献信息

• [EN] NOVEL COMPOUNDS EFFECTIVE AS XANTHINE OXIDASE INHIBITORS, METHOD FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS EFFICACES EN TANT QU'INHIBITEURS DE XANTHINE OXYDASE, LEUR PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE LES CONTENANT
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2010093191A3

  公开（公告）日：2010-12-09