triethyl 2-fluoro-3-oxo-5-phenyl-2-phosphonopentanoate | 590365-58-5

• 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 2-fluoro-3-oxo-5-phenyl-2-phosphonopentanoate
• 英文别名: Ethyl 2-[diethoxy(oxido)phosphaniumyl]-2-fluoro-3-oxo-5-phenylpentanoate；ethyl 2-[diethoxy(oxido)phosphaniumyl]-2-fluoro-3-oxo-5-phenylpentanoate
• CAS: 590365-58-5
• 化学式: C₁₇H₂₄FO₆P
• 分子量: 374.346
• InChiKey: YTACZRAVZBDWAL-UHFFFAOYSA-N

物化性质

• 沸点：
  454.7±45.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  triethyl 2-fluoro-3-oxo-5-phenyl-2-phosphonopentanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以76%的产率得到ethyl (Z)-2-fluoro-5-phenylpent-2-enoate
  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
• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 3-苯丙酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以60%的产率得到triethyl 2-fluoro-3-oxo-5-phenyl-2-phosphonopentanoate
  参考文献：
  名称：

  Tandem reduction–olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-Ψ[(Z)-CFC]-Gly dipeptide isostere

  摘要：

  (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.

  DOI：

  10.1016/j.tet.2006.09.096

文献信息

• 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.