methyl (2S,3R,αS)-2-deuterio-3-[N-(α-methylbenzyl)-amino]-3-phenylpropanoate | 1332928-65-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3R,αS)-2-deuterio-3-[N-(α-methylbenzyl)-amino]-3-phenylpropanoate
• CAS: 1332928-65-0
• 化学式: C₁₈H₂₁NO₂
• 分子量: 284.362
• InChiKey: KIAYOUZTHYVACZ-VRZCFQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,αS)-2-deuterio-3-[N-(α-methylbenzyl)-amino]-3-phenylpropanoate 在 甲基溴化镁 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以94%的产率得到(3S,4R,αS)-N(1)-(α-methylbenzyl)-3-deuterio-4-phenylazetidin-2-one
  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：

  tert-butyl cinnamate 在 正丁基锂 、 氯化亚砜 、 ammonium cerium (IV) nitrate 、 水 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 22.5h， 生成 methyl (2S,3R,αS)-2-deuterio-3-[N-(α-methylbenzyl)-amino]-3-phenylpropanoate
  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