3-(2-fluoro-5-hydroxyphenyl)-alanine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(2-fluoro-5-hydroxyphenyl)-alanine
• 英文别名: 6-fluoro-meta-tyrosine；6-fluoro-m-tyrosine；6-F-meta-tyrosine；2-Amino-3-(2-fluoro-5-hydroxyphenyl)propanoic acid
• 化学式: C₉H₁₀FNO₃
• mdl: MFCD18647577
• 分子量: 199.182
• InChiKey: YTYMWTLCTJSNDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-bromo-4-(tert-butyl)phenol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 sodium acetate 、 乙酸酐 、 氟化氢吡啶 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 51.2h， 生成 3-(2-fluoro-5-hydroxyphenyl)-alanine
  参考文献：
  名称：

  [EN] FLUORINE RADIOLABELLING PROCESS
  [FR] PROCÉDÉ DE RADIOMARQUAGE AU FLUOR

  摘要：

  公开号：

  WO2012004567A3

文献信息

• Fluorine Radiolabelling Process
  申请人：Gouveneur Veronique

  公开号：US20130190529A1

  公开（公告）日：2013-07-25

  The invention relates to a process for producing a process for producing an 18 F-labelled compound, the process comprising treating a compound of formula (I) wherein EDG is an electron-donating group selected from —OH, —OR 4 , —NHR 5 and —NR 55 R 5 ; R 1 , R 2 , X 1 and X 2 are as defined herein; and R 3 is selected from H, X 3 and X 4 , wherein X 3 is a monodentate cleavable surrogate group, and X 4 is a bidentate cleavable surrogate group which is bonded (a) to said X 1 or X 2 and (b) to the ring carbon atom para to EDG; with [ 18 F]fluoride in the presence of an oxidant, thereby producing, when R 3 in the compound of formula (I) is H, an 18 F-labelled compound of formula (II), wherein EDG is as defined above and R 1 , R 2 , X 1 and X 2 are as defined herein; or thereby producing, when R 3 in the compound of formula (I) is said monodentate cleavable surrogate group X 3 , a compound of formula (IIa), wherein EDG′ is O, NR 5 , —NR 55 R 5 or [OR 4 ] + , and wherein R 4 , R 5 , R 55 , R 1 , R 2 , X 1 , X 2 and X 3 are as defined herein; or thereby producing, when R 3 in the compound of formula (I) is said bidentate cleavable surrogate group X 4 , a compound of formula (IIc) or a compound of formula (IId), wherein EDG′ is O, NR 5 , —NR 55 R 5 or [OR 4 ] + , and wherein R 4 , R 5 , R 55 , R 1 , R 2 , X 1 , X 2 and X 4 are as defined herein

  该发明涉及一种用于制备18F标记化合物的过程，该过程包括处理以下结构的化合物（I）：其中EDG是从—OH、—OR4、—NHR5和—NR55R5中选择的电子给体基团；R1、R2、X1和X2如本文所定义；以及R3从H、X3和X4中选择，其中X3是一种可单齿解离替代基团，而X4是一种双齿可解离替代基团，它与EDG对位的环碳原子上键合（a）到所述的X1或X2，（b）到EDG的对位环碳原子；在氧化剂存在下用[18F]氟化物处理，从而产生当化合物（I）中的R3为H时，化合物（II）的18F标记化合物，其中EDG如上所定义，而R1、R2、X1和X2如本文所定义；或者从而产生当化合物（I）中的R3为所述的可单齿解离替代基团X3时，化合物（IIa），其中EDG'为O、NR5、—NR55R5或[OR4]+，而R4、R5、R55、R1、R2、X1、X2和X3如本文所定义；或者从而产生当化合物（I）中的R3为所述的双齿可解离替代基团X4时，化合物（IIc）或化合物（IId），其中EDG'为O、NR5、—NR55R5或[OR4]+，而R4、R5、R55、R1、R2、X1、X2和X4如本文所定义。
• Nucleophilic approach for preparing radiolabeled imaging agents and associated compounds
  申请人：——

  公开号：US20040034246A1

  公开（公告）日：2004-02-19

  Radiolabeled fluorinated compounds useful for imaging in the diagnosis of Parkinson's Disease are disclosed. Methods and kits for their synthesis are also disclosed.

  本发明公开了用于帕金森病诊断成像的放射性标记氟化合物。同时，还公开了其合成的方法和试剂盒。
• Syntheses of 6-fluoro-meta-tyrosine and of its metabolites
  作者：Jamie T Konkel、Junfa Fan、B Jayachandran、Kenneth L Kirk

  DOI：10.1016/s0022-1139(02)00013-1

  日期：2002.5

  6-Fluoro-meta-tyrosine (1) was prepared from 2-fluoro-5-hydroxybenzaldehyde (6) based on an Erlenmeyer-Plochl azlactone strategy. Products of expected metabolism of the amino acid, including 6-fluoro-meta-tyramine (2) and its O-sulfate conjugate (3), (2-fluoro-5-hydrxoyphenyl)acetic acid (4), and 6-fluoro-meta-octopamine (5) also were prepared from 1. The use of a recently reported ultrasound-catalyzed Henry reaction facilitated the preparation of the tyramine derivative 2. The compounds synthesized are available for high performance liquid chromatography (HPLC) standards in positron emission tomography (PET) studies employing 6-[F-18]fluoro-meta-tyrosine and as reference samples for metabolic studies of the amino acid. (C) 2002 Elsevier Science B.V. All rights reserved.
• Selective fluorination of m-tyrosine by OF2
  作者：Babak Behnam Azad、Rezwan Ashique、Raman Chirakal、Gary J. Schrobilgen

  DOI：10.1016/j.jfluchem.2007.08.004

  日期：2008.1

  Fluorine-18 labeled aromatic amino acids are routinely used as tracers in positron emission tomography (PET) to study in vivo metabolic processes. The most versatile method for the production of such radiotracers is electrophilic fluorination of the aromatic amino acid with [F-18]F-2, which is most commonly produced by the gas-phase nuclear reaction O-18(p, n)F-18. Although [F-18]F-2 is the major product, considerable amounts of [F-18]OF2 (UP to 20%) are also produced. Electrophilic fluorination reactions Of L-phenylalanine, 3-nitro-L-tyrosine, 4-nitro-DL-phenylalanine, 3,4-dihydroxyphenyl-L-alanine (L-DOPA), 3-O-methyl-L-DOPA, 3,4-dimethoxy-L-phenylalanine, p-tyrosine and o-tyrosine in H2O and of m-tyrosine in anhydrous HF (aHF), CF3SO3H, CF3COOH, CH3COOH, HCOOH and H2O using OF2 were investigated. Although F-2 is an efficient fluorinating agent in aRF, electrophilic fluorination reactions using OF2 were shown to be most efficient in less acidic media such as H2O. In addition, and contrary to reports that OF2 and F-2 have similar reactivities, m-tyrosine was the only aromatic system studied that was fluorinated by OF2 and this was optimum in H2O for the fluorinated m-tyrosine isomers (total yield, 4.35 +/- 0.04%). The presence of [F-18]OF2 byproduct has no significant impact on the fluorination of aromatic amino acids investigated in this study and the subsequent production of their corresponding F-18-labeled radiotracers for patient use. (C) 2007 Elsevier B.V. All rights reserved.
• FLUORINATION OF AROMATIC RING SYSTEMS
  申请人：NUtech Ventures

  公开号：EP3284736B1

  公开（公告）日：2021-03-03