8-[18F]fluorooctanoyl chloride

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 8-[18F]fluorooctanoyl chloride
• 英文别名: 8-(18F)fluoranyloctanoyl chloride
• 化学式: C₈H₁₄ClFO
• 分子量: 179.652
• InChiKey: DHTDPANMZLIFNK-LMANFOLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-[18F]fluorooctanoyl chloride 、 2-monopalmitoylglycerol 生成 1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol
  参考文献：
  名称：

  Ido, Tatsuo; Nagata, Shinnji; Mukoyoshi, Masanori, Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 631 - 633

  摘要：

  DOI：
• 作为产物：
  描述：

  [¹⁸F]-8-fluorooctanoic acid 在 氯化亚砜 作用下， 反应 0.08h， 生成 8-[18F]fluorooctanoyl chloride
  参考文献：
  名称：

  [F-18]labeling of 1,2-diacylglycerols

  摘要：

  We have developed two kinds of [F-18]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(omega-[F-18]fluoroacyl)-2-acylglycerols (1*,2-[F-18]FDAGs) and 2-(omega-[F-18]fluoroacyl)-1-acylglycerols (1,2*-[F-18]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[F-18]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with omega-[F-18]fluoroacyl chlorides (method A) and 1-(16-[F-18]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C16,C16)) and 1-(8-[F-18]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[F-18]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(omega-[F-18]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(omega-bromoacyl)-1-acylglycerol with [F-18]F- (method B) and 2-(16-[F-18]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C16)) and [F-18]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[F-18]FDAGs were obtained in radiochemical yields of 8-35 % (based on [F-18]F-) with radiochemical purities of > 97 % and the purified 1,2*-[F-18]FDAGs were in radiochemical yields of 5-15 % with radiochemical purities of > 95 %. The total synthesis time from the start of the reactive [F-18]F- production, including HPLC purification, was 100 - 135 min (method A) and 115 - 175 min (method B), respectively. It has already been used for more than 100 preparations of 1*,2-[F-18]FDAG(C16,C16), 1*,2-[F-18]FDAG(C8, C16), and 1,2*-[F-18]FDAG(C16,C16), 1,2*-[F-18]FDAG(C16,C8) for animal studies.

  DOI：

  10.1002/1099-1344(200008)43:9<943::aid-jlcr379>3.0.co;2-v

文献信息

• [F-18]labeling of 1,2-diacylglycerols
  作者：Toshihiro Takahashi、Tatsuo Ido、Shinji Nagata、Ren Iwata

  DOI：10.1002/1099-1344(200008)43:9<943::aid-jlcr379>3.0.co;2-v

  日期：2000.8

  We have developed two kinds of [F-18]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(omega-[F-18]fluoroacyl)-2-acylglycerols (1*,2-[F-18]FDAGs) and 2-(omega-[F-18]fluoroacyl)-1-acylglycerols (1,2*-[F-18]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[F-18]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with omega-[F-18]fluoroacyl chlorides (method A) and 1-(16-[F-18]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C16,C16)) and 1-(8-[F-18]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[F-18]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(omega-[F-18]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(omega-bromoacyl)-1-acylglycerol with [F-18]F- (method B) and 2-(16-[F-18]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C16)) and [F-18]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[F-18]FDAGs were obtained in radiochemical yields of 8-35 % (based on [F-18]F-) with radiochemical purities of > 97 % and the purified 1,2*-[F-18]FDAGs were in radiochemical yields of 5-15 % with radiochemical purities of > 95 %. The total synthesis time from the start of the reactive [F-18]F- production, including HPLC purification, was 100 - 135 min (method A) and 115 - 175 min (method B), respectively. It has already been used for more than 100 preparations of 1*,2-[F-18]FDAG(C16,C16), 1*,2-[F-18]FDAG(C8, C16), and 1,2*-[F-18]FDAG(C16,C16), 1,2*-[F-18]FDAG(C16,C8) for animal studies.
• Ido, Tatsuo; Nagata, Shinnji; Mukoyoshi, Masanori, Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 631 - 633
  作者：Ido, Tatsuo、Nagata, Shinnji、Mukoyoshi, Masanori、Yamaguchi, Koji、Iwata, Ren、et al.

  DOI：——

  日期：——