2-hydroxy-3-methoxy-5-(3-fluoropropyl)benzoic acid | 669089-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-3-methoxy-5-(3-fluoropropyl)benzoic acid
• 英文别名: 5-(3-Fluoropropyl)-2-hydroxy-3-methoxybenzoic acid；5-(3-fluoropropyl)-2-hydroxy-3-methoxybenzoic acid
• CAS: 669089-90-1
• 化学式: C₁₁H₁₃FO₄
• 分子量: 228.22
• InChiKey: UMYJKJMVIVDFNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-烯丙基-2-氨甲基吡咯烷 、 2-hydroxy-3-methoxy-5-(3-fluoropropyl)benzoic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 以48%的产率得到(S)-N-[(1-allyl-2-pyrrolidinyl)methyl]-2-hydroxy-3-methoxy-5-(3'-fluoropropyl)benzamide
  参考文献：
  名称：

  11C-Fallypride: radiosynthesis and preliminary evaluation of a novel dopamine D2/D3 receptor PET radiotracer in non-human primate brain

  摘要：

  Fallypride [benzamide, 5-(3-fluoropropyl)-2,3-dimethoxy-N-[(2S)-1-(2-propenyl)-2-pyrrolidinyl]methyl]-, CAS RN 166173-78-0] is a selective dopamine D2/D3 receptor antagonist. Carbon-11 labeled fallypride may serve as a radiotracer for use in biomedical imaging technique positron emission tomography (PET). The precursor, 5-(3-fluoropropyl)-2-hydroxy-3-metboxy-N-[(2S)-1-(2-propenyl)-2-pyrrolidinyl]methyl]benzamide was synthesized from 2-hydroxy-3-methoxy-5-(2-propenyl)benzoic acid, methyl ester in seven steps with approximately 10% overall chemical yield. Using this precursor C-11-fallypride was produced by radiolabeling with C-11-methyl iodide in 25-40% radiochemical yields with specific activities of 200-1000 Ci/mmol. PET imaging studies in nonhuman primates with C-11-fallypride showed radiotracer localization in dopaminergic brain regions such as caudate, putamen, thalamus and cortex. This regional localization of C-11-fallypride is similar to that observed previously for F-18-fallypride. The results suggest C-11-fallypride is a useful PET radiotracer for imaging dopamine D2/D3 receptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.020
• 作为产物：
  描述：

  5-烯丙基-3-甲氧基水杨酸甲酯 在 吡啶 、 sodium hydroxide 、 硼烷 、 四丁基氟化铵 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 2-hydroxy-3-methoxy-5-(3-fluoropropyl)benzoic acid
  参考文献：
  名称：

  11C-Fallypride: radiosynthesis and preliminary evaluation of a novel dopamine D2/D3 receptor PET radiotracer in non-human primate brain

  摘要：

  Fallypride [benzamide, 5-(3-fluoropropyl)-2,3-dimethoxy-N-[(2S)-1-(2-propenyl)-2-pyrrolidinyl]methyl]-, CAS RN 166173-78-0] is a selective dopamine D2/D3 receptor antagonist. Carbon-11 labeled fallypride may serve as a radiotracer for use in biomedical imaging technique positron emission tomography (PET). The precursor, 5-(3-fluoropropyl)-2-hydroxy-3-metboxy-N-[(2S)-1-(2-propenyl)-2-pyrrolidinyl]methyl]benzamide was synthesized from 2-hydroxy-3-methoxy-5-(2-propenyl)benzoic acid, methyl ester in seven steps with approximately 10% overall chemical yield. Using this precursor C-11-fallypride was produced by radiolabeling with C-11-methyl iodide in 25-40% radiochemical yields with specific activities of 200-1000 Ci/mmol. PET imaging studies in nonhuman primates with C-11-fallypride showed radiotracer localization in dopaminergic brain regions such as caudate, putamen, thalamus and cortex. This regional localization of C-11-fallypride is similar to that observed previously for F-18-fallypride. The results suggest C-11-fallypride is a useful PET radiotracer for imaging dopamine D2/D3 receptors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.020

文献信息

• 11C-Fallypride: radiosynthesis and preliminary evaluation of a novel dopamine D2/D3 receptor PET radiotracer in non-human primate brain
  作者：Jogeshwar Mukherjee、Bingzhi Shi、Bradley T Christian、Sankha Chattopadhyay、Tanjore K Narayanan

  DOI：10.1016/j.bmc.2003.10.020

  日期：2004.1

  Fallypride [benzamide, 5-(3-fluoropropyl)-2,3-dimethoxy-N-[(2S)-1-(2-propenyl)-2-pyrrolidinyl]methyl]-, CAS RN 166173-78-0] is a selective dopamine D2/D3 receptor antagonist. Carbon-11 labeled fallypride may serve as a radiotracer for use in biomedical imaging technique positron emission tomography (PET). The precursor, 5-(3-fluoropropyl)-2-hydroxy-3-metboxy-N-[(2S)-1-(2-propenyl)-2-pyrrolidinyl]methyl]benzamide was synthesized from 2-hydroxy-3-methoxy-5-(2-propenyl)benzoic acid, methyl ester in seven steps with approximately 10% overall chemical yield. Using this precursor C-11-fallypride was produced by radiolabeling with C-11-methyl iodide in 25-40% radiochemical yields with specific activities of 200-1000 Ci/mmol. PET imaging studies in nonhuman primates with C-11-fallypride showed radiotracer localization in dopaminergic brain regions such as caudate, putamen, thalamus and cortex. This regional localization of C-11-fallypride is similar to that observed previously for F-18-fallypride. The results suggest C-11-fallypride is a useful PET radiotracer for imaging dopamine D2/D3 receptors. (C) 2003 Elsevier Ltd. All rights reserved.