ethyl (2E)-2-fluoro-2-[2-[tri(propan-2-yl)silyloxymethyl]cyclopentylidene]acetate | 1620387-62-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl (2E)-2-fluoro-2-[2-[tri(propan-2-yl)silyloxymethyl]cyclopentylidene]acetate
• CAS: 1620387-62-3
• 化学式: C₁₉H₃₅FO₃Si
• 分子量: 358.569
• InChiKey: MULJNBKTFSXOIP-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 2-{[(triisopropylsilyl)oxy]methyl}cyclopentanone 在 异丙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以56%的产率得到
  参考文献：
  名称：

  Z-Selective Horner–Wadsworth–Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CF C]-Pro-OH dipeptide isostere

  摘要：

  The Horner-Wadsworth-Emmons reactions of 2-fluoro-2-diethylphosphonoacetic acid with 241(triisopropylsilyl)oxy]methyl)cyclopentanone (2-TOM-cyclopentanone) using methylrnagnesium chloride furnished the corresponding tetra-substituted fluoroolefin in a Z-selective manner (E/Z = 9:91). A facile synthesis of rac-N-Cbz-Gly-Psi[(Z)-CF=C]-Pro-OH as a dipeptide isostere was achieved based on the Z-selective Horner-Wadsworth-Emmons reaction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.077

文献信息

• Z-Selective Horner–Wadsworth–Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CF C]-Pro-OH dipeptide isostere
  作者：Shigeki Sano、Tomoya Matsumoto、Hiroshi Nanataki、Shota Tempaku、Michiyasu Nakao

  DOI：10.1016/j.tetlet.2014.09.077

  日期：2014.11

  The Horner-Wadsworth-Emmons reactions of 2-fluoro-2-diethylphosphonoacetic acid with 241(triisopropylsilyl)oxy]methyl)cyclopentanone (2-TOM-cyclopentanone) using methylrnagnesium chloride furnished the corresponding tetra-substituted fluoroolefin in a Z-selective manner (E/Z = 9:91). A facile synthesis of rac-N-Cbz-Gly-Psi[(Z)-CF=C]-Pro-OH as a dipeptide isostere was achieved based on the Z-selective Horner-Wadsworth-Emmons reaction. (C) 2014 Elsevier Ltd. All rights reserved.
• E-Selective Horner–Wadsworth–Emmons reaction of 2-OBO-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(E)-CFC]-Pro-OH dipeptide isostere
  作者：Shigeki Sano、Tomoya Matsumoto、Michiyasu Nakao

  DOI：10.1016/j.tetlet.2014.06.063

  日期：2014.8

  The Horner-Wadsworth-Emmons reactions of ethyl 2-fluoro-2-diethylphosphonoacetate with 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone (2-OBO-cyclopentanone) using n-butyl-lithium furnished the corresponding tetra-substituted fluoroolefin in an E-selective manner (E:Z = 95:5). A facile synthesis of rac-N-Cbz-Gly-Psi[(E)-CF=C]-Pro-OH as a dipeptide isostere was achieved based on the E-selective Horner-Wadsworth-Emmons reaction. (C) 2014 Elsevier Ltd. All rights reserved.