(1-(pyridin-2-ylmethyl)pyrrolidin-2-yl)methanol | 132902-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1-(pyridin-2-ylmethyl)pyrrolidin-2-yl)methanol
• 英文别名: [(2S)-1-(pyridin-2-ylmethyl)pyrrolidin-2-yl]methanol
• CAS: 132902-38-6
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: HMANPRPKKYMPJL-NSHDSACASA-N

物化性质

• 沸点：
  303.3±17.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-(pyridin-2-ylmethyl)pyrrolidin-2-yl)methanol 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到((1R,2S)-1-Oxy-1-pyridin-2-ylmethyl-pyrrolidin-2-yl)-methanol
  参考文献：
  名称：

  Homochiral Amine Oxides in the Enantioselective Reduction of Ketones

  摘要：

  文中描述了多种新型同手性吡咯烷酮N-氧化物衍生物的合成过程。其中若干种化合物被发现能高效催化硼烷对α-氯苯乙酮的还原反应，生成(S)-2-氯-1-苯乙醇，化学产率极佳且对映体过量率达96%。

  DOI：

  10.1055/s-1997-5770
• 作为产物：
  描述：

  吡啶-2-甲醛 、 L-脯氨醇 在 sodium tetrahydroborate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到(1-(pyridin-2-ylmethyl)pyrrolidin-2-yl)methanol
  参考文献：
  名称：

  Design and synthesis of a tridentate ligand inspired by the phenomenon of self-assembly catalysis and its application in the asymmetric alkynylation of N-(diphenylphosphinoyl) imines

  摘要：

  On the basis of the phenomenon of self-assembly catalysis, a tridentate ligand was designed and synthesized in two steps. The application in alkynylation of N-(diphenylphosphinoyl) imines gave the expected products. Aromatic, heteroaromatic N-(diphenylphosphinoyl) imines were employed and gave optically active propargylic amines in good yields (up to 89%) and excellent enantioselectivities (up to 96%) by a simple experimental procedure. The direct use of sulfone amides in the alkynylation of N-(diphenylphosphinoyl) aliphatic imines made this method very attractive. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.020

文献信息

• Chiral ligands containing heteroatoms. 6. 1-(2-Pyridylmethyl)pyrrolidine in the chiral catalysis of addition of diethylzinc to benzaldehyde.
  作者：Giorgio Chelucci、Massimo Falorni、Giampaolo Giacomelli

  DOI：10.1016/s0957-4166(00)80448-6

  日期：1990.1
• Homochiral Amine Oxides in the Enantioselective Reduction of Ketones
  作者：Ian O'Neil、Carl Turner、S. Kalindjian

  DOI：10.1055/s-1997-5770

  日期：1997.7

  The synthesis of a number of novel homochiral prolinol N-oxide derivatives is described. Several of these were found to catalyse the borane reduction of α-chloroacetophenone to (S)-2-chloro-1-phenylethanol in excellent chemical yield and in 96% ee.

  文中描述了多种新型同手性吡咯烷酮N-氧化物衍生物的合成过程。其中若干种化合物被发现能高效催化硼烷对α-氯苯乙酮的还原反应，生成(S)-2-氯-1-苯乙醇，化学产率极佳且对映体过量率达96%。
• Design and synthesis of a tridentate ligand inspired by the phenomenon of self-assembly catalysis and its application in the asymmetric alkynylation of N-(diphenylphosphinoyl) imines
  作者：Wenjin Yan、Peng Li、Jingchao Feng、Dong Wang、Shaoqun Zhu、Xianxing Jiang、Rui Wang

  DOI：10.1016/j.tetasy.2010.07.020

  日期：2010.8

  On the basis of the phenomenon of self-assembly catalysis, a tridentate ligand was designed and synthesized in two steps. The application in alkynylation of N-(diphenylphosphinoyl) imines gave the expected products. Aromatic, heteroaromatic N-(diphenylphosphinoyl) imines were employed and gave optically active propargylic amines in good yields (up to 89%) and excellent enantioselectivities (up to 96%) by a simple experimental procedure. The direct use of sulfone amides in the alkynylation of N-(diphenylphosphinoyl) aliphatic imines made this method very attractive. (C) 2010 Elsevier Ltd. All rights reserved.