tert-butyl (2Z)-2-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopentylidene]-2-fluoroacetate | 174076-00-7

• 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: tert-butyl (2Z)-2-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopentylidene]-2-fluoroacetate
• CAS: 174076-00-7
• 化学式: C₁₈H₃₃FO₃Si
• 分子量: 344.542
• InChiKey: NMVDNTJBVWBVLS-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2Z)-2-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopentylidene]-2-fluoroacetate 在 水 、 二异丁基氢化铝 作用下， 以 乙醚 、 正戊烷 为溶剂， 以93%的产率得到(Z)-1-(1-fluoro-2-oxoethylidene)-2-(t-butyldimethylsilyloxymethyl)cyclopentane
  参考文献：
  名称：

  Fluoroolefin containing dipeptide isosteres as inhibitors of dipeptidyl peptidase IV(CD26)

  摘要：

  (Z)-(S)Ala-psi[CF=C]-(RS)-Pro containing N,O-diacylhydroxamic acid type protease inhibitors have been prepared for the study of the influence of prolylamide bond geometry on the inhibition of dipeptidyl peptidase IV(CD26). The synthesis is based upon the use of tert-butyl alpha-fluoro-alpha-trimethylsilylacetate in a variation of the Peterson olefination procedure to construct the necessary functionalized fluoroolefin.

  DOI：

  10.1016/0040-4020(95)00912-r
• 作为产物：
  描述：

  tert-butyl α-fluoroacetate 在 酒石酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 3.83h， 生成 tert-butyl (2Z)-2-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopentylidene]-2-fluoroacetate
  参考文献：
  名称：

  Fluoroolefin containing dipeptide isosteres as inhibitors of dipeptidyl peptidase IV(CD26)

  摘要：

  (Z)-(S)Ala-psi[CF=C]-(RS)-Pro containing N,O-diacylhydroxamic acid type protease inhibitors have been prepared for the study of the influence of prolylamide bond geometry on the inhibition of dipeptidyl peptidase IV(CD26). The synthesis is based upon the use of tert-butyl alpha-fluoro-alpha-trimethylsilylacetate in a variation of the Peterson olefination procedure to construct the necessary functionalized fluoroolefin.

  DOI：

  10.1016/0040-4020(95)00912-r

文献信息

• Fluoroolefin containing dipeptide isosteres as inhibitors of dipeptidyl peptidase IV(CD26)
  作者：John T. Welch、Jian Lin

  DOI：10.1016/0040-4020(95)00912-r

  日期：1996.1

  (Z)-(S)Ala-psi[CF=C]-(RS)-Pro containing N,O-diacylhydroxamic acid type protease inhibitors have been prepared for the study of the influence of prolylamide bond geometry on the inhibition of dipeptidyl peptidase IV(CD26). The synthesis is based upon the use of tert-butyl alpha-fluoro-alpha-trimethylsilylacetate in a variation of the Peterson olefination procedure to construct the necessary functionalized fluoroolefin.