3-[(S)-3-dimethylaminopyrrolidin-1-ylmethyl]phenol | 1246299-48-8

• 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: 3-[(S)-3-dimethylaminopyrrolidin-1-ylmethyl]phenol
• 英文别名: 3-[[(3S)-3-(dimethylamino)pyrrolidin-1-yl]methyl]phenol
• CAS: 1246299-48-8
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: UQXYDPWRKDUEPK-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  26.71
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 tert-butyl N-((3S)-1-((3-hydroxyphenyl)methyl)pyrrolidin-3-yl)carbamate 在 甲酸 作用下， 以 水 为溶剂， 反应 4.0h， 以71%的产率得到3-[(S)-3-dimethylaminopyrrolidin-1-ylmethyl]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

文献信息

• Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry
  作者：Mickael Pouliquen、Jérôme Blanchet、Michaël De Paolis、B. Rema Devi、Jacques Rouden、Marie-Claire Lasne、Jacques Maddaluno

  DOI：10.1016/j.tetasy.2010.04.038

  日期：2010.6

  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.