tert-butyl 5-(18F)fluoranylindole-1-carboxylate | 1403599-72-3

• 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: tert-butyl 5-(18F)fluoranylindole-1-carboxylate
• CAS: 1403599-72-3
• 化学式: C₁₃H₁₄FNO₂
• 分子量: 234.26
• InChiKey: PCZRVRIBJPHEBB-UMSOTBISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-5-溴吲哚 在 吡啶 、 18-冠醚-6 、 1,1'-(phenyl-λ³-iodanediyl)-bis(4-methoxypyridinium)-bis(trifluormethansulfonate) 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 3.02h， 生成 tert-butyl 5-(18F)fluoranylindole-1-carboxylate
  参考文献：
  名称：

  用 [18F] 氟化物水溶液对 PET 进行镍介导的氧化氟化

  摘要：

  提出了一种用于从明确的镍配合物与氧化剂和氟化物水溶液形成碳氟键的一步氧化氟化，这使得具有 PE​​T 成像潜力的复杂小分子的直接和实用的 (18)F 后期氟化成为可能。

  DOI：

  10.1021/ja3084797

文献信息

• Discovery of 7-[¹⁸F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo
  作者：Boris D. Zlatopolskiy、Johannes Zischler、Dominique Schäfer、Elizaveta A. Urusova、Mehrab Guliyev、Olesia Bannykh、Heike Endepols、Bernd Neumaier

  DOI：10.1021/acs.jmedchem.7b01245

  日期：2018.1.11

  Tryptophan and its metabolites are involved in different physiological and pathophysiological processes. Consequently, positron emission tomography (PET) tracers addressing tryptophan metabolic pathways should allow the detection of different pathologies like neurological disorders and cancer. Herein we report an efficient method for the preparation of fluorotryptophans labeled in different positions with F-18 and their biological evaluation. 4-7-[F-18]Fluorotryptophans ([F-18]FTrps) were prepared according to a modified protocol of alcohol-enhanced Cu-mediated radiofluorination in 30-53% radiochemical yields. In vitro experiments demonstrated high cellular uptake of 4-7[F-18]FTrps in different tumor cell lines. 4, 5-, and 6-[F-18]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[F-18]FTrp demonstrated a high in vivo stability and enabled a clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains. Moreover 7-[F-18]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[F-18]FTrp represents a highly promising PET probe for imaging of Trp metabolism.
• FLUORINATION METHOD
  申请人：Oxford University Innovation Limited

  公开号：US20170137341A1

  公开（公告）日：2017-05-18

  The present invention relates to a process for producing an organic compound comprising an 18 F atom. The compounds comprising an 18 F can be useful as PET ligands for use in diagnostics and/or scanning. The process of the invention comprises treating an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp 2 hybridised carbon atom, with (i) 18 F— and (ii) a copper compound. The invention also provides the use of an organoboron compound, which organoboron compound comprises a boron atom bonded to an sp 2 hybridised carbon atom, in a process for producing an organic compound comprising an 18 F atom, which process comprises treating the organoboron compound with (i) 18 F— and (ii) a copper compound. The invention also provides a compound of formula (XXXVII): wherein: each PG A is independently H or an alcohol protecting group; PG B is H or a carboxylic acid protecting group; each PG C is independently an amine protecting group; Z is a group selected from a boronic ester group, a boronic acid group, a borate group, and a trifluoroborate group; and a is an integer from 0 to 4.
• METHOD OF FLUORINATION USING IODONIUM YLIDES
  申请人：The General Hospital Corporation

  公开号：US20170121300A1

  公开（公告）日：2017-05-04

  A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18 F is described. Processes, intermediates, reagents and radiolabelled compounds are described.
• Nickel-Mediated Oxidative Fluorination for PET with Aqueous [¹⁸F] Fluoride
  作者：Eunsung Lee、Jacob M. Hooker、Tobias Ritter

  DOI：10.1021/ja3084797

  日期：2012.10.24

  A one-step oxidative fluorination for carbon-fluorine bond formation from well-defined nickel complexes with oxidant and aqueous fluoride is presented, which enables a straightforward and practical (18)F late-stage fluorination of complex small molecules with potential for PET imaging.

  提出了一种用于从明确的镍配合物与氧化剂和氟化物水溶液形成碳氟键的一步氧化氟化，这使得具有 PE​​T 成像潜力的复杂小分子的直接和实用的 (18)F 后期氟化成为可能。