triethyl 3-cyclohexyl-2-fluoro-3-oxo-phosphonopropanoate | 188645-65-0

• 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: triethyl 3-cyclohexyl-2-fluoro-3-oxo-phosphonopropanoate
• 英文别名: Ethyl 3-cyclohexyl-2-diethoxyphosphoryl-2-fluoro-3-oxopropanoate
• CAS: 188645-65-0
• 化学式: C₁₅H₂₆FO₆P
• 分子量: 352.34
• InChiKey: JURVSUXNDDVNNB-UHFFFAOYSA-N

物化性质

• 沸点：
  427.7±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  triethyl 3-cyclohexyl-2-fluoro-3-oxo-phosphonopropanoate 在 氯化铵 、 magnesium chloride 作用下， 生成 乙基3-环己基-2-氟-3-氧代丙酸酯
  参考文献：
  名称：

  P-C Bond Cleavage of Triethyl 2-Fluoro-3-oxo-2-phosphonoacetates with Magnesium Chloride: A Synthesis of α-Fluoro-β-keto Esters

  摘要：

  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.

  DOI：

  10.1080/00397919708003055
• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 环己甲酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 triethyl 3-cyclohexyl-2-fluoro-3-oxo-phosphonopropanoate
  参考文献：
  名称：

  Tandem reduction–olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters

  摘要：

  A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH4 in EtOH was developed. The one-pot reaction gave alpha-fluoro-alpha,beta-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00778-0

文献信息

• 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.
• Tandem reduction–olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters
  作者：Shigeki Sano、Katsuyuki Saito、Yoshimitsu Nagao

  DOI：10.1016/s0040-4039(03)00778-0

  日期：2003.5

  A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH4 in EtOH was developed. The one-pot reaction gave alpha-fluoro-alpha,beta-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Tandem reduction–olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-Ψ[(Z)-CFC]-Gly dipeptide isostere
  作者：Shigeki Sano、Yoko Kuroda、Katsuyuki Saito、Yukiko Ose、Yoshimitsu Nagao

  DOI：10.1016/j.tet.2006.09.096

  日期：2006.12

  (Z)-alpha-Fluoro-alpha,beta-unsaturated esters (Z)-7a-f were stereoselectively prepared by a tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates 6a-f with NaBH4 in EtOH. A concise synthesis of Cbz-Gly-Psi[(Z)-CF=C]-Gly (26) as a dipeptide isostere was achieved via the tandem reduction-olefination of the corresponding 2-acyl-2-fluoro-2-phosphonoacetate 20. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.