methyl 2-methylene-3-(4-fluorophenyl)pentanoate | 847654-01-7

• 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: methyl 2-methylene-3-(4-fluorophenyl)pentanoate
• 英文别名: Methyl 3-(4-fluorophenyl)-2-methylidenepentanoate
• CAS: 847654-01-7
• 化学式: C₁₃H₁₅FO₂
• 分子量: 222.259
• InChiKey: IEKBMYGTUSKDTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methylene-3-(4-fluorophenyl)pentanoate 在 CHIRALCEL OD 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 (S)-methyl 3-(4-fluorophenyl)-2-methylenepentanoate 、 (R)-methyl 3-(4-fluorophenyl)-2-methylenepentanoate
  参考文献：
  名称：

  Expedient synthesis of β,β-disubstituted α-methylenepropionates

  摘要：

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.002
• 作为产物：
  描述：

  methyl 3-(4-fluorophenyl)-3-hydroxy-2-methylenepropanoate 在 四丁基溴化铵 、 N,N-二甲基甲酰胺 草酰氯 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 3.42h， 生成 methyl 2-methylene-3-(4-fluorophenyl)pentanoate
  参考文献：
  名称：

  Expedient synthesis of β,β-disubstituted α-methylenepropionates

  摘要：

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.002

文献信息

• Expedient synthesis of β,β-disubstituted α-methylenepropionates
  作者：Kallolmay Biswas、Christoph Börner、Josepe Gimeno、Paul J. Goldsmith、Daniella Ramazzotti、Angela L.K. So、Simon Woodward

  DOI：10.1016/j.tet.2004.12.002

  日期：2005.2

  Baylis-Hillman alcohols are excellent sources of the allylic halides ArCH=CH(CH2X)(CO2R) (X = Br. Cl: R-1= Me, Et. Bu'). The Z double bond isomers are attained in high isomeric purity (> 14: 1. ZIE). The halides are chemo- and regiospecifically transformed into the acrylates (ArCHR2)C(=CH2)(CO2R1) on treatment with Zn(R-2)(2) (R-2 =Me. Et, CH2TMS, CH(2)SiMe(2)Ome) or PrZnBr- in the presence of catalytic amounts of copper(1) salts (0.5-20 mol%) in high yield. (C) 2004 Elsevier Ltd. All rights reserved.