tert-butyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate | 249939-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate
• 英文别名: tert-butyl 4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate；tert-butyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methylbut-2-enoate
• CAS: 249939-36-4
• 化学式: C₁₆H₂₀F₃NO₃
• 分子量: 331.335
• InChiKey: OAIOHSZDKUKTBY-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-2-methyl-2-butenoate 在 sodium tetrahydroborate 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到tert-butyl (2RS,3RS)-4,4,4-trifluoro-3-(4-methoxyanilino)-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：

  丙酸叔丁酯 、 N-(4-Methoxyphenyl)trifluoroacetimidoyl Chloride 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以91%的产率得到tert-butyl (Z)-4,4,4-trifluoro-3-(4-methoxyanilino)-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