ethyl 2-(diphenylphosphoryl)-2-fluoroacetate | 126706-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(diphenylphosphoryl)-2-fluoroacetate
• 英文别名: ethyl diphenyl phosphinoxy-fluoroacetate；Ethyl (diphenylphosphoryl)(fluoro)acetate；ethyl 2-diphenylphosphoryl-2-fluoroacetate
• CAS: 126706-15-8
• 化学式: C₁₆H₁₆FO₃P
• 分子量: 306.273
• InChiKey: XKHZGLYXWHKPCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(diphenylphosphoryl)-2-fluoroacetate 、 2,4-Bis-(4-fluoro-phenyl)-6-isopropyl-pyrimidine-5-carbaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到(Z)-3-[2,4-Bis-(4-fluoro-phenyl)-6-isopropyl-pyrimidin-5-yl]-2-fluoro-acrylic acid ethyl ester
  参考文献：
  名称：

  一种新型的氟取代的HMG-COA还原酶抑制剂的对映选择性合成

  摘要：

  描述了通过将手性烯酸酯加入氟代醛中以高光学纯度合成新的氟代取代的3-羟基-3-甲基戊二酰辅酶A还原酶抑制剂。

  DOI：

  10.1016/s0040-4039(01)93462-8
• 作为产物：
  描述：

  二苯基乙氧基膦 、 溴氟乙酸乙酯 反应 4.5h， 以38%的产率得到ethyl 2-(diphenylphosphoryl)-2-fluoroacetate
  参考文献：
  名称：

  Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner–Wadsworth–Emmons Olefination

  摘要：

  A versatile and general catalytic strategy has been developed for the alpha-arylation of phosphonoacetates utilizing parallel microscale experimentation. These a-substituted phosphonoacetates are widely useful, notably as substrates in the Horner-Wadsworth-Emmons-type olefinations. However, the current routes to these products involve harsh conditions, limiting the variety of functionality. The reported method can be used with a variety of aryl chlorides and aryl bromides, including several heterocyclic examples.

  DOI：

  10.1021/acs.joc.5b01887

文献信息

• BAADER, E.;BARTMANN, W.;BECK, G.;BELOW, P.;BERGMANN, A.;JENDRALLA, H.;KES+, TETRAHEDRON LETT., 30,(1989) N8, C. 5115-5118
  作者：BAADER, E.、BARTMANN, W.、BECK, G.、BELOW, P.、BERGMANN, A.、JENDRALLA, H.、KES+

  DOI：——

  日期：——
• BECK, GERHARD;BARTMANN, WILHELM;WESS, GUNTHER;GRANZER, ERNOLD
  作者：BECK, GERHARD、BARTMANN, WILHELM、WESS, GUNTHER、GRANZER, ERNOLD

  DOI：——

  日期：——
• Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner–Wadsworth–Emmons Olefination
  作者：Kelsey F. VanGelder、Melinda Wang、Marisa C. Kozlowski

  DOI：10.1021/acs.joc.5b01887

  日期：2015.10.16

  A versatile and general catalytic strategy has been developed for the alpha-arylation of phosphonoacetates utilizing parallel microscale experimentation. These a-substituted phosphonoacetates are widely useful, notably as substrates in the Horner-Wadsworth-Emmons-type olefinations. However, the current routes to these products involve harsh conditions, limiting the variety of functionality. The reported method can be used with a variety of aryl chlorides and aryl bromides, including several heterocyclic examples.
• Enantioselective synthesis of a new fluoro-substituted HMG-COA reductase inhibitor
  作者：E. Baader、W. Bartmann、G. Beck、P. Below、A. Bergmann、H. Jendralla、K. Keßeler、G. Wess

  DOI：10.1016/s0040-4039(01)93462-8

  日期：——

  The synthesis of a new fluoro-substituted 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor in high optical purity via addition of the chiral enolate to fluoro aldehyde is described.

  描述了通过将手性烯酸酯加入氟代醛中以高光学纯度合成新的氟代取代的3-羟基-3-甲基戊二酰辅酶A还原酶抑制剂。