Octanoic acid, 2-(diethoxyphosphinyl)-2-fluoro-3-oxo-, ethyl ester | 188645-64-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Octanoic acid, 2-(diethoxyphosphinyl)-2-fluoro-3-oxo-, ethyl ester
• 英文别名: ethyl 2-diethoxyphosphoryl-2-fluoro-3-oxooctanoate
• CAS: 188645-64-9
• 化学式: C₁₄H₂₆FO₆P
• 分子量: 340.329
• InChiKey: ZDQAFPYTTPVGBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Octanoic acid, 2-(diethoxyphosphinyl)-2-fluoro-3-oxo-, ethyl ester 在 sodium tetrahydroborate 、 4% Pd/C 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 2-fluoro-1-octanol
  参考文献：
  名称：

  Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae

  摘要：

  Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at beta position of C=C bond, as well as the reaction conditions. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.011
• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 己酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 Octanoic acid, 2-(diethoxyphosphinyl)-2-fluoro-3-oxo-, ethyl ester
  参考文献：
  名称：

  Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae

  摘要：

  Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at beta position of C=C bond, as well as the reaction conditions. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.02.011

文献信息

• A Facile P-C Bond Cleavage of 2-Fluoro-2-Phosphonyl-1,3-Dicarbonyl Compounds on Silica Gel
  作者：Dae Young Kim

  DOI：10.1080/00397910008087140

  日期：2000.4

  alpha-Fluoro-beta-keto esters and alpha-fluoromalonates were prepared by the P-C bond cleavage of 2-fluoro-2-phosphonyl-1,3-dicarbonyl compounds on wet silica gel.
• P-C Bond Cleavage of Triethyl 2-Fluoro-3-oxo-2-phosphonoacetates with Magnesium Chloride: A Synthesis of α-Fluoro-β-keto Esters
  作者：Dae Young Kim、Jin Seok Choi、Dae Yong Rhie

  DOI：10.1080/00397919708003055

  日期：1997.3

  P-C bond cleavage of triethyl 2-fluoro-3-oxo-2-phosphonoacetates in the presence of magnesium chloride provides a synthetic route to alpha-fluoro-beta-keto esters.
• Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae
  作者：Fan Luo、Dengfu Lu、Yuefa Gong

  DOI：10.1016/j.molcatb.2011.02.011

  日期：2011.7

  Biocatalytic reduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae underwent smoothly and yielded (S)-2-fluorinated alkanols with high enantioselectivities. The conversion rate was markedly depending on the configuration of alkene moiety of the substrate, the chain length of alkyl group at beta position of C=C bond, as well as the reaction conditions. (C) 2011 Elsevier B.V. All rights reserved.