2-<1-<4-(tert-butyldimethylsiloxy)butyl>>-1-pyrroline | 152905-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2-<1-<4-(tert-butyldimethylsiloxy)butyl>>-1-pyrroline
• 英文别名: tert-butyl-[4-(3,4-dihydro-2H-pyrrol-5-yl)butoxy]-dimethylsilane
• CAS: 152905-72-1
• 化学式: C₁₄H₂₉NOSi
• 分子量: 255.476
• InChiKey: ZZHIVDXNEVWVLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<1-<4-(tert-butyldimethylsiloxy)butyl>>-1-pyrroline 在 正丁基锂 、 (R,R)-ethylene-1,2-bis(η⁵-4,5,6,7-tetrahydro-1-indenyl)zirconium dichloride (R)-1,1'-binaphth-2,2'-diolate 、 苯硅烷 、 氢气 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 65.0 ℃ 、551.58 kPa 条件下， 反应 10.0h， 以85%的产率得到(+)-2-<1-<4-(tert-butyldimethylsiloxy)butyl>>pyrrolidine
  参考文献：
  名称：

  Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Scope and Limitations

  摘要：

  The asymmetric hydrogenation of imines with a chiral titanocene catalyst derived from Brintzinger's ansatitanocene complex 1 proceeds to afford amines with good to excellent enantioselectivity. The catalyst is particularly effective for the reduction of cyclic imines. For these substrates enantiomeric excesses from 95 to 99% were achieved. For acyclic imines lower enantiomeric excesses were observed. The reason for this is likely due to the fact that the acyclic imines are mixtures of anti and syn isomers which interconvert during the reaction. The catalyst was found to be tolerant of many functional groups found in organic synthesis. Thus the reaction represents an effective method for the synthesis of chiral cyclic amines.

  DOI：

  10.1021/ja00099a012
• 作为产物：
  描述：

  2-甲基吡咯啉 、 1-碘-3-[(叔-丁基二甲基硅烷基)氧基]丙烷 在 lithium diisopropyl amide 作用下， 生成 2-<1-<4-(tert-butyldimethylsiloxy)butyl>>-1-pyrroline
  参考文献：
  名称：

  Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Scope and Limitations

  摘要：

  The asymmetric hydrogenation of imines with a chiral titanocene catalyst derived from Brintzinger's ansatitanocene complex 1 proceeds to afford amines with good to excellent enantioselectivity. The catalyst is particularly effective for the reduction of cyclic imines. For these substrates enantiomeric excesses from 95 to 99% were achieved. For acyclic imines lower enantiomeric excesses were observed. The reason for this is likely due to the fact that the acyclic imines are mixtures of anti and syn isomers which interconvert during the reaction. The catalyst was found to be tolerant of many functional groups found in organic synthesis. Thus the reaction represents an effective method for the synthesis of chiral cyclic amines.

  DOI：

  10.1021/ja00099a012

文献信息

• Synthesis of highly enantiomerically enriched cyclic amines by the catalytic asymmetric hydrogenation of cyclic imines
  作者：Christopher A. Willoughby、Stephen L. Buchwald

  DOI：10.1021/jo00079a001

  日期：1993.12

  The asymmetric hydrogenation of cyclic ketimines with a chiral titanocene catalyst affords amines with excellent enantioselectivity under a variety of conditions. The reaction is general for cyclic imines of ring size 5-7 and exhibits a high degree of functional group compatibility.
• Catalytic Asymmetric Hydrogenation of Imines with a Chiral Titanocene Catalyst: Scope and Limitations
  作者：Christopher A. Willoughby、Stephen L. Buchwald

  DOI：10.1021/ja00099a012

  日期：1994.10

  The asymmetric hydrogenation of imines with a chiral titanocene catalyst derived from Brintzinger's ansatitanocene complex 1 proceeds to afford amines with good to excellent enantioselectivity. The catalyst is particularly effective for the reduction of cyclic imines. For these substrates enantiomeric excesses from 95 to 99% were achieved. For acyclic imines lower enantiomeric excesses were observed. The reason for this is likely due to the fact that the acyclic imines are mixtures of anti and syn isomers which interconvert during the reaction. The catalyst was found to be tolerant of many functional groups found in organic synthesis. Thus the reaction represents an effective method for the synthesis of chiral cyclic amines.