triethyl 2-isopropyl-3-oxo-5-phenyl-2-phosphonopentanoate | 590365-66-5

• 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: triethyl 2-isopropyl-3-oxo-5-phenyl-2-phosphonopentanoate
• CAS: 590365-66-5
• 化学式: C₂₀H₃₁O₆P
• 分子量: 398.436
• InChiKey: FJSSPWGEYSMIMV-UHFFFAOYSA-N

物化性质

• 沸点：
  483.8±40.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  27.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  triethyl 2-isopropyl-3-oxo-5-phenyl-2-phosphonopentanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以9%的产率得到2-异丙基-5-苯基-2-戊烯酸乙酯
  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-(二乙氧基次膦酰基)-3-甲基丁酸乙酯 、 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 21.0h， 以13%的产率得到triethyl 2-isopropyl-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