(3R)-1-(2-甲氧基乙基)-3-吡咯烷醇 | 216666-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (3R)-1-(2-甲氧基乙基)-3-吡咯烷醇
• 英文名称: (R)-1-(2-methoxyethyl)-3-hydroxypyrrolidine
• 英文别名: (R)-1-(2-methoxyethyl)pyrrolidin-3-ol；(3R)-1-(2-methoxyethyl)pyrrolidin-3-ol
• CAS: 216666-99-8
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: DHCISEVTZIPVQJ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-1-(2-甲氧基乙基)-3-吡咯烷醇 在 lithium aluminium tetrahydride 、 迭氮酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 甲苯 、 苯 为溶剂， 反应 8.0h， 生成 (S)-1-(2-methoxyethyl)-3-(N-cyclohexylideneamino)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：

  甲氧基乙酰氯 、 (R)-3-吡咯烷醇 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 9.0h， 以88%的产率得到(3R)-1-(2-甲氧基乙基)-3-吡咯烷醇
  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

• METHODS AND COMPOSITIONS OF TREATING A FLAVIVIRIDAE FAMILY VIRAL INFECTION
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20150152064A1

  公开（公告）日：2015-06-04

  Briefly described, embodiments of this disclosure include compounds, pharmaceutical compositions, methods of treating a host infected with a virus from the Flaviviridae family of viruses, methods of inhibiting HCV replication in a host, methods of inhibiting the binding of NS4B polypeptide to the 3′UTR of HCV negative strand RNA in a host, methods of treating liver fibrosis in a host, and the like.

  简单描述一下，本公开的实施例包括化合物、药物组合物、治疗感染黄病毒科病毒的宿主的方法、抑制宿主中HCV复制的方法、抑制NS4B多肽与HCV负链RNA的3'UTR结合的方法、治疗宿主肝纤维化的方法等。
• US8940730B2
  申请人：——

  公开号：US8940730B2

  公开（公告）日：2015-01-27
• US9149463B2
  申请人：——

  公开号：US9149463B2

  公开（公告）日：2015-10-06
• 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.