(2S)-2-氨基-3-(2-氟-5-羟基苯基)丙酸 | 148613-12-1

• 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
• 中文名称: (2S)-2-氨基-3-(2-氟-5-羟基苯基)丙酸
• 中文别名: 2-氨基-3-(2-氟-5-羟基-苯基)-丙酸
• 英文名称: (2S)-2-Amino-3-(2-fluoro-5-hydroxyphenyl) propanoic acid
• 英文别名: 6-fluoro-L-meta-tyrosine；6-fluoro-meta-tyrosine；2-fluoro-5-hydroxy-L-phenylalanine；(2S)-2-amino-3-(2-fluoro-5-hydroxyphenyl)propanoic acid
• CAS: 148613-12-1
• 化学式: C₉H₁₀FNO₃
• 分子量: 199.182
• InChiKey: YTYMWTLCTJSNDC-QMMMGPOBSA-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：
  0.22
• 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：

  2-氟-5-甲氧基苯甲醛 在 吡啶 、 sodium tetrahydroborate 、 二溴亚砜 、 氢碘酸 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.67h， 生成 (2S)-2-氨基-3-(2-氟-5-羟基苯基)丙酸
  参考文献：
  名称：

  Asymmetric synthesis of fluorinated l-tyrosine and

  摘要：

  A convenient asymmetric synthesis of (2S)-2-amino-3-(2-fluoro-5-hydroxyphenyl) propanoic acid, (2S)-2-amino-3-(4-fluoro-3-hydroxyphenyl) propanoic acid and (2S)-2-amino-3-(2-fluoro-4-hydroxyphenyl) propanoic acid is described. Key steps include the synthesis of the benzyl bromides, the alkylation of the glycine enolate derivative ((S)-Boc-BMI) and the hydrolysis of the alkylated Boc-BMI.

  DOI：

  10.1016/0022-1139(94)03085-e

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。
• Method of fluorination using iodonium ylides
  申请人：The General Hospital Corporation

  公开号：US10259800B2

  公开（公告）日：2019-04-16

  A process for fluorination of aromatic compounds employing iodonium ylides and applicable to radiofluorination using 18F is described. Processes, intermediates, reagents and radiolabelled compounds are described.

  描述了一种使用碘化亚烯并适用于使用18F进行放射性氟化的芳香化合物氟化的过程。描述了过程、中间体、试剂和标记化合物。
• [EN] COMPOUNDS AND KITS FOR PREPARING IMAGING AGENTS AND METHODS OF IMAGING<br/>[FR] COMPOSES ET KITS DE PREPARATION D'AGENTS D'IMAGERIE ET PROCEDES D'IMAGERIE
  申请人：GEN ELECTRIC

  公开号：WO2005023317A1

  公开（公告）日：2005-03-17

  Compounds that include a targeting moiety bound to a regioselective leaving group are useful for preparing imaging agents. The imaging agents can be isolated from by­products derived from the leaving group based on differences in the chemical attributes (e.g., net charge or polarity) of the molecules or physical attributes of the molecules through the use of a solid support. Methods of producing an imaging agent include the steps of providing a compound that includes a targeting moiety bound to a support via a linker group that contains a site for regioselective substitution of a detectable species, contacting the compound with a solution containing the detectable species, and recovering the imaging agent. Kits which include a first container (5) having therein a solution (31) containing a detectable species and a second container (2) having therein a compound that includes a targeting moiety bound to a support (30) via a leaving group that contains a site for regioselective substitution of the detectable species are also useful for preparing imaging agents.

  将包括与一个区域选择性离去基团结合的靶向基团的化合物用于制备成像剂是有用的。这些成像剂可以通过固体支持物来分离出来，基于分子的化学属性（例如净电荷或极性）或物理属性之间的差异，以此与离去基团衍生的副产物进行区分。制备成像剂的方法包括以下步骤：提供一个包含通过链连接基团与支持物相结合的靶向基团的化合物，该链连接基团包含一个用于区域选择性取代可检测物种的位点；将该化合物与含有可检测物种的溶液接触；并回收成像剂。还有一种用于制备成像剂的工具包，其中包括一个第一容器（5），其中含有一个含有可检测物种的溶液（31），以及一个第二容器（2），其中含有一个通过含有一个用于区域选择性取代可检测物种的离去基团的位点而与支持物（30）相结合的靶向基团的化合物。
• 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。
• Compounds and kits for preparing imaging agents and methods of imaging
  申请人：Johnson Fletcher Bruce

  公开号：US20050049487A1

  公开（公告）日：2005-03-03

  Compounds that include a targeting moiety bound to a regioselective leaving group are useful for preparing imaging agents. The imaging agents can be isolated from by-products derived from the leaving group based on differences in the chemical attributes (e.g., net charge or polarity) of the molecules or physical attributes of the molecules through the use of a solid support. Methods of producing an imaging agent include the steps of providing a compound that includes a targeting moiety bound to a support via a linker group that contains a site for regioselective substitution of a detectable species, contacting the compound with a solution containing the detectable species, and recovering the imaging agent. Kits which include a first container having therein a solution containing a detectable species and a second container having therein a compound that includes a targeting moiety bound to a support via a leaving group that contains a site for regioselective substitution of the detectable species are also useful for preparing imaging agents.

  含有定向基团结合到区域选择性离去基团的化合物对于制备成像剂是有用的。成像剂可以通过固体支持物来分离出来，该支持物基于分子的化学属性（例如净电荷或极性）或物理属性与离去基团衍生物之间的差异。制备成像剂的方法包括以下步骤：提供一种化合物，该化合物包括通过含有可检测物质的置换位点结合到支持物上的定向基团，将该化合物与包含可检测物质的溶液接触，然后回收成像剂。同时，包括第一容器和第二容器的套装对于制备成像剂也是有用的，其中第一容器中含有可检测物质的溶液，第二容器中含有通过含有置换可检测物质的离去基团结合到支持物上的定向基团的化合物。