(S)-1-((o-methoxyphenyl)methyl)-3-aminopyrrolidine | 216668-01-8

• 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: (S)-1-((o-methoxyphenyl)methyl)-3-aminopyrrolidine
• 英文别名: (3S)-1-(2-methoxybenzyl)pyrrolidin-3-amine；(3S)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-amine
• CAS: 216668-01-8
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: MBAGLGVPJNVVJH-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-((o-methoxyphenyl)methyl)-3-aminopyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (S)-1-((o-methoxyphenyl)methyl)-3-(cyclohexylamino)pyrrolidine
  参考文献：
  名称：

  Structure-Selectivity Relationship in Alkyllithium−Aldehyde Condensations Using 3-Aminopyrrolidine Lithium Amides as Chiral Auxiliaries

  摘要：

  A nonracemizing route to a set of chiral 3-aminopyrrolidines, based on 4-hydroxy-(L)-proline, is described. The induction potential of the lithium amides derived from these diamines has then been investigated in the asymmetric addition of alkyllithium compounds onto various aldehydes. Enantiomeric excesses up to 76% have been obtained in the case of the condensation of n-butyllithium onto o-tolualdehyde under standard experimental conditions (THF, -78 degrees C). Interestingly, the presence of a second asymmetric center, such as an alpha-methylbenzyl group, on the lateral 3-amino group gives access, according to its configuration, to one or the other of the 1-o-tolylpentan-1-ol enantiomers.

  DOI：

  10.1021/jo9810260
• 作为产物：
  描述：

  (S)-1-((o-methoxyphenyl)methyl)-3-azidopyrrolidine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以97%的产率得到(S)-1-((o-methoxyphenyl)methyl)-3-aminopyrrolidine
  参考文献：
  名称：

  Structure-Selectivity Relationship in Alkyllithium−Aldehyde Condensations Using 3-Aminopyrrolidine Lithium Amides as Chiral Auxiliaries

  摘要：

  A nonracemizing route to a set of chiral 3-aminopyrrolidines, based on 4-hydroxy-(L)-proline, is described. The induction potential of the lithium amides derived from these diamines has then been investigated in the asymmetric addition of alkyllithium compounds onto various aldehydes. Enantiomeric excesses up to 76% have been obtained in the case of the condensation of n-butyllithium onto o-tolualdehyde under standard experimental conditions (THF, -78 degrees C). Interestingly, the presence of a second asymmetric center, such as an alpha-methylbenzyl group, on the lateral 3-amino group gives access, according to its configuration, to one or the other of the 1-o-tolylpentan-1-ol enantiomers.

  DOI：

  10.1021/jo9810260

文献信息

• [EN] 2-PHENYL-3H-IMIDAZO[4,5-B]PYRIDINE DERIVATES USEFUL AS INHIBITORS OF MAMMALIAN TYROSINE KINASE ROR1 ACTIVITY<br/>[FR] DÉRIVÉS DE 2-PHÉNYL-3H-IMIDAZO[4,5-B]PYRIDINE UTILISÉS COMME INHIBITEURS DE L'ACTIVITÉ DE LA TYROSINE KINASE DE MAMMIFÈRE ROR1
  申请人：KANCERA AB

  公开号：WO2016124553A1

  公开（公告）日：2016-08-11

  A compound of formula (I´) or (I´´) or a pharmaceutically acceptable salt thereof. The compound is an inhibitor of mammalian kinase enzyme activity, including ROR1 tyrosine kinase activity and may be used in the treatment of disorders associated with such activity.

  化合物的化学式（I´）或（I´´）或其药学上可接受的盐。该化合物是哺乳动物激酶酶活性的抑制剂，包括ROR1酪氨酸激酶活性，并可用于治疗与该活性相关的疾病。
• Structure-Selectivity Relationship in Alkyllithium−Aldehyde Condensations Using 3-Aminopyrrolidine Lithium Amides as Chiral Auxiliaries
  作者：Aline Corruble、Jean-Yves Valnot、Jacques Maddaluno、Pierre Duhamel

  DOI：10.1021/jo9810260

  日期：1998.11.1

  A nonracemizing route to a set of chiral 3-aminopyrrolidines, based on 4-hydroxy-(L)-proline, is described. The induction potential of the lithium amides derived from these diamines has then been investigated in the asymmetric addition of alkyllithium compounds onto various aldehydes. Enantiomeric excesses up to 76% have been obtained in the case of the condensation of n-butyllithium onto o-tolualdehyde under standard experimental conditions (THF, -78 degrees C). Interestingly, the presence of a second asymmetric center, such as an alpha-methylbenzyl group, on the lateral 3-amino group gives access, according to its configuration, to one or the other of the 1-o-tolylpentan-1-ol enantiomers.