tert-butyl (E)-2-deuterio-3-(3'-fluorophenyl)propenoate | 1332928-88-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: tert-butyl (E)-2-deuterio-3-(3'-fluorophenyl)propenoate
• CAS: 1332928-88-7
• 化学式: C₁₃H₁₅FO₂
• 分子量: 223.251
• InChiKey: IKDGGSOWHJECTM-QRJRHGAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (E)-2-deuterio-3-(3'-fluorophenyl)propenoate 、 (S)-(-)-N-苄基-1-苯基-乙胺 在 正丁基锂 、 2-羟基吡啶 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以73%的产率得到tert-butyl (2R,3R,αS)-2-deuterio-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(3'-fluorophenyl)propanoate
  参考文献：
  名称：

  Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives

  摘要：

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.008
• 作为产物：
  描述：

  二乙基膦酰基乙酸叔丁酯 在 重水 、 potassium carbonate 作用下， 反应 54.0h， 生成 tert-butyl (E)-2-deuterio-3-(3'-fluorophenyl)propenoate
  参考文献：
  名称：

  Asymmetric synthesis of syn- and anti-α-deuterio-β3-phenylalanine derivatives

  摘要：

  The conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of aryl substituted tert-butyl cinnamate esters followed by reaction of the resultant lithium beta-amino enolates with D2O provides access to anti configured alpha-deuterio-beta-aminocinnamate esters in high dr. The corresponding syn configured diastereoisomers were also obtained with high diastereoselectivity via the conjugate addition of lithium (5)-N-benzyl-N-(alpha-methylbenzyl)amide to a range of tert-butyl alpha-deuteriocinnamate esters followed by reaction of the resultant lithium beta-amino enolates with 2-pyridone. After deprotection both the syn- and anti-diastereoisomers of the corresponding alpha-deuterio-beta(3)-amino acids can be isolated in high dr. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.008