8-fluorooctanoyl chloride | 764-88-5

• 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-fluorooctanoyl chloride
• 英文别名: 8-fluoro-octanoyl chloride；8-Fluor-octanoylchlorid；8-Fluorooctanoyl chloride
• CAS: 764-88-5
• 化学式: C₈H₁₄ClFO
• 分子量: 180.65
• InChiKey: DHTDPANMZLIFNK-UHFFFAOYSA-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-fluorooctanoyl chloride 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 苯 为溶剂， 反应 21.0h， 生成 2-(8-fluorooctanoyl)-1-palmitoylglycerol
  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
• 作为产物：
  描述：

  8-溴辛酸 在 草酰氯 、 lithium hydroxide monohydrate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 8-fluorooctanoyl chloride
  参考文献：
  名称：

  Synthesis of a monofluoro 3-alkyl-2-hydroxy-1,4-naphthoquinone: a potential anti-malarial drug

  摘要：

  Monofluorinated 3-alkyl-2-hydroxy-1,4-naphthoquinone 4 was prepared in eight steps from commercially available 8-bromooctanoic acid (10). The key step involved L-proline-catalyzed three-component reductive alkylation (TCRA) of 2-hydroxy-1,4-naphthoquinone (5) with the optically active aldehyde 7. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.054

文献信息

• Toxic Fluorine Compounds. X.¹ ι-Fluorocarboxylic Acid Chlorides, Anhydrides, Amides, and Anilides
  作者：F. L. M. PATTISON、R. R. FRASER、G. J. O'NEILL、J. F. K. WILSHIRE

  DOI：10.1021/jo01114a017

  日期：1956.8
• Synthesis of a monofluoro 3-alkyl-2-hydroxy-1,4-naphthoquinone: a potential anti-malarial drug
  作者：Eliana E. Kim、Evans O. Onyango、Liangfeng Fu、Gordon W. Gribble

  DOI：10.1016/j.tetlet.2015.10.054

  日期：2015.12

  Monofluorinated 3-alkyl-2-hydroxy-1,4-naphthoquinone 4 was prepared in eight steps from commercially available 8-bromooctanoic acid (10). The key step involved L-proline-catalyzed three-component reductive alkylation (TCRA) of 2-hydroxy-1,4-naphthoquinone (5) with the optically active aldehyde 7. (C) 2015 Elsevier Ltd. All rights reserved.
• Toxic Fluorine Compounds. XI.¹ ι-Fluoroaldehydes
  作者：J. F. K. Wilshire、F. L. M. Pattison

  DOI：10.1021/ja01600a051

  日期：1956.10
• EP1082327A4
  申请人：——

  公开号：EP1082327A4

  公开（公告）日：2003-04-16
• PERFLUORINATED ORGANO SUBSTITUTED CYCLOSILOXANES AND COPOLYMERS PREPARED FROM THESE CYCLOSILOXANES
  申请人：Archimica (Florida), Inc.

  公开号：EP1082327A1

  公开（公告）日：2001-03-14