(S)-1-tert-butoxycarbonyl-2-[(indolinyl)methyl]pyrrolidine | 198218-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-1-tert-butoxycarbonyl-2-[(indolinyl)methyl]pyrrolidine
• CAS: 198218-54-1
• 化学式: C₁₈H₂₆N₂O₂
• 分子量: 302.417
• InChiKey: GUUBSSWFCJLBLA-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-tert-butoxycarbonyl-2-[(indolinyl)methyl]pyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到(S)-1-methyl-2-[(indolinyl)methyl]pyrrolidine
  参考文献：
  名称：

  Chiral Lewis Acid Controlled Synthesis (CLAC Synthesis): Chiral Lewis Acids Influence the Reaction Course in Asymmetric Aldol Reactions for the Synthesis of Enantiomeric Dihydroxythioester Derivatives in the Presence of Chiral Diamines Derived from L-Proline

  摘要：

  AbstractBoth enantiomers of 2,3‐dihy‐droxythioester derivatives were prepared with almost perfect stereochemical control by chiral Lewis acid controlled synthesis (CLAC synthesis). CLAC synthesis means synthesis of all individual diastereomers or enantiomers from the same starting materials by designing chiral Lewis acids. For example, (Z)‐1‐ethyl‐thio‐1‐(trimethylsiloxy)‐2‐(tert‐butyldi‐methylsiloxy)ethene (1) reacted with aldehydes in the presence of chiral tin(II) Lewis acids using (S)‐1‐methyl‐2‐[(isoin‐dolinyl)methyl]pyrrolidine (4) and (S)‐1‐methyl‐2‐[(indolinyl)methyl]pyrrolidine (5) to afford enantiomeric dihydroxy‐thioester derivatives. Chiral diamines 4 and 5, which were readily prepared from L‐proline, differ only in the fusion point of the benzene ring connected to the pyrrolidine moiety. The unique selectivities were ascribed to the conformational difference between the chiral tin(II) Lewis acids of chiral diamines 4 and 5, and the function of chiral sources for obtaining high selectivities has also been clarified.

  DOI：

  10.1002/chem.19970030914
• 作为产物：
  描述：

  Boc-L-Pro-indoline 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到(S)-1-tert-butoxycarbonyl-2-[(indolinyl)methyl]pyrrolidine
  参考文献：
  名称：

  Chiral Lewis Acid Controlled Synthesis (CLAC Synthesis): Chiral Lewis Acids Influence the Reaction Course in Asymmetric Aldol Reactions for the Synthesis of Enantiomeric Dihydroxythioester Derivatives in the Presence of Chiral Diamines Derived from L-Proline

  摘要：

  AbstractBoth enantiomers of 2,3‐dihy‐droxythioester derivatives were prepared with almost perfect stereochemical control by chiral Lewis acid controlled synthesis (CLAC synthesis). CLAC synthesis means synthesis of all individual diastereomers or enantiomers from the same starting materials by designing chiral Lewis acids. For example, (Z)‐1‐ethyl‐thio‐1‐(trimethylsiloxy)‐2‐(tert‐butyldi‐methylsiloxy)ethene (1) reacted with aldehydes in the presence of chiral tin(II) Lewis acids using (S)‐1‐methyl‐2‐[(isoin‐dolinyl)methyl]pyrrolidine (4) and (S)‐1‐methyl‐2‐[(indolinyl)methyl]pyrrolidine (5) to afford enantiomeric dihydroxy‐thioester derivatives. Chiral diamines 4 and 5, which were readily prepared from L‐proline, differ only in the fusion point of the benzene ring connected to the pyrrolidine moiety. The unique selectivities were ascribed to the conformational difference between the chiral tin(II) Lewis acids of chiral diamines 4 and 5, and the function of chiral sources for obtaining high selectivities has also been clarified.

  DOI：

  10.1002/chem.19970030914