tert-butyl (S)-(2-hydroxybenzyl)(pyrrolidin-3-yl)carbamate | 1246299-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tert-butyl (S)-(2-hydroxybenzyl)(pyrrolidin-3-yl)carbamate
• CAS: 1246299-61-5
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: YPHLLQWVDRQFOT-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 tert-butyl (S)-(2-hydroxybenzyl)(pyrrolidin-3-yl)carbamate 在 甲酸 作用下， 以 水 为溶剂， 反应 4.0h， 以81%的产率得到2-{[methyl-((S)-1-methylpyrrolidin-3-yl)amino]methyl}phenol
  参考文献：
  名称：

  Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry

  摘要：

  Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.038
• 作为产物：
  描述：

  tert-butyl (S)-(1-benzylpyrrolidin-3-yl)(2-hydroxybenzyl)carbamate 在 10% palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以97%的产率得到tert-butyl (S)-(2-hydroxybenzyl)(pyrrolidin-3-yl)carbamate
  参考文献：
  名称：

  Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry

  摘要：

  Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.038