methyl 8-fluorooctanoate | 616205-77-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 8-fluorooctanoate
• 英文别名: 8-Fluor-octansaeuremethylester
• CAS: 616205-77-7
• 化学式: C₉H₁₇FO₂
• 分子量: 176.231
• InChiKey: XMVRKCZNUSCAEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  203.9±10.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 8-fluorooctanoate 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 以95%的产率得到8-氟辛酸
  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
• 作为产物：
  描述：

  8-羟基辛酸甲酯 在 二乙胺基三氟化硫 作用下， 生成 methyl 8-fluorooctanoate
  参考文献：
  名称：

  Evidence for an octanoate synthase operating during the biosynthesis of piliformic acid in Poronia piliformis

  摘要：

  Sodium [1-C-13]-octanoate is incorporated intact into the C-8 unit of piliformic acid 1 in Poronia piliformis whereas sodium [3-C-13]-decanoate 2 is incorporated into this unit only after prior beta-oxidation to [1-C-13]-acetyl-CoA. Also 8-fluoraoctanaote 3 is utilised by P. piliformis as an intact unit to generate 9-fluoropiliformic acid 5 whereas 10-fluorodecanoate 4 is not. These results suggest that octanoate is biosynthesised de novo for secondary metabolism and is not assimilated from higher fatty acids by beta-oxidation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00102-6

文献信息

• C-HALOGEN BOND FORMATION
  申请人：Groves John T.

  公开号：US20140227184A1

  公开（公告）日：2014-08-14

  Methods of halogenating a carbon containing compound having an sp3 C—H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond are provided. The halogenated products of the methods are provided.

  本文提供了卤代含有sp3 C—H 键的碳化合物的卤代方法。本文提供了卤代含有Cl或Br的碳化合物，然后通过亲核取代反应与F进行氟化的方法。本文提供了直接氧化C—H氟化含有sp3 C—H 键的碳化合物的方法。本文提供了上述方法的卤代产物。
• Aqueous fluorination of carboxylic acid salts
  作者：Vytautas Grakauskas

  DOI：10.1021/jo01260a040

  日期：1969.8
• Asymmetric syntheses of potential anti-malarial drugs designed from Fieser's 2-hydroxy-3-(2-methyloctyl)naphthalene-1,4-dione
  作者：Louise M. Fisher、Eliana E. Kim、Nicolai V. Moskalev、Gordon W. Gribble

  DOI：10.24820/ark.5550190.p011.206

  日期：——
• 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.
• Evidence for an octanoate synthase operating during the biosynthesis of piliformic acid in Poronia piliformis
  作者：Helen Culceth、Jens Fuchser、Steven J Moss、Jens Nieschalk、David O'Hagan

  DOI：10.1016/s0040-4039(98)00102-6

  日期：1998.4

  Sodium [1-C-13]-octanoate is incorporated intact into the C-8 unit of piliformic acid 1 in Poronia piliformis whereas sodium [3-C-13]-decanoate 2 is incorporated into this unit only after prior beta-oxidation to [1-C-13]-acetyl-CoA. Also 8-fluoraoctanaote 3 is utilised by P. piliformis as an intact unit to generate 9-fluoropiliformic acid 5 whereas 10-fluorodecanoate 4 is not. These results suggest that octanoate is biosynthesised de novo for secondary metabolism and is not assimilated from higher fatty acids by beta-oxidation. (C) 1998 Elsevier Science Ltd. All rights reserved.