methyl 4,4,5,5,5-pentafluoro-3-[(4-methoxyphenyl)imino]-2-methyl-2-butenoate | 249939-39-7

• 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 4,4,5,5,5-pentafluoro-3-[(4-methoxyphenyl)imino]-2-methyl-2-butenoate
• 英文别名: Methyl 4,4,5,5,5-pentafluoro-3-(4-methoxyphenyl)imino-2-methylpentanoate
• CAS: 249939-39-7
• 化学式: C₁₄H₁₄F₅NO₃
• 分子量: 339.262
• InChiKey: LIKSVGWFZWUKAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4,4,5,5,5-pentafluoro-3-[(4-methoxyphenyl)imino]-2-methyl-2-butenoate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 ethyl (2RS,3RS)-3-amino-4,4,4-trifluoro-2-methylbutanoate
  参考文献：
  名称：

  First Highly Diastereoselective Synthesis of syn α-Methyl β-Fluoroalkyl β-Amino Esters

  摘要：

  [GRAPHICS]A new two-step approach for the diastereoselective synthesis of the syn alpha-methyl beta-fluoroalkyl beta-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated beta-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester enolates, with Znl(2)/NaBH4 as the reducing agent. The process takes place with high syn diastereoselectivity and good to excellent yields. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction.

  DOI：

  10.1021/ol990774o
• 作为产物：
  描述：

  丙酸甲酯 、 N-(p-methoxyphenyl)-2,2,3,3,3-pentafluoropropanoimidoyl chloride 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以71%的产率得到methyl 4,4,5,5,5-pentafluoro-3-[(4-methoxyphenyl)imino]-2-methyl-2-butenoate
  参考文献：
  名称：

  First Highly Diastereoselective Synthesis of syn α-Methyl β-Fluoroalkyl β-Amino Esters

  摘要：

  [GRAPHICS]A new two-step approach for the diastereoselective synthesis of the syn alpha-methyl beta-fluoroalkyl beta-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated beta-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester enolates, with Znl(2)/NaBH4 as the reducing agent. The process takes place with high syn diastereoselectivity and good to excellent yields. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction.

  DOI：

  10.1021/ol990774o

文献信息

• First Highly Diastereoselective Synthesis of <i>s</i><i>yn</i> α-Methyl β-Fluoroalkyl β-Amino Esters
  作者：Santos Fustero、Belén Pina、Marta García de la Torre、Antonio Navarro、Carmen Ramírez de Arellano、Antonio Simón

  DOI：10.1021/ol990774o

  日期：1999.10.1

  [GRAPHICS]A new two-step approach for the diastereoselective synthesis of the syn alpha-methyl beta-fluoroalkyl beta-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated beta-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester enolates, with Znl(2)/NaBH4 as the reducing agent. The process takes place with high syn diastereoselectivity and good to excellent yields. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction.