(S)-3-methoxymethoxypyrrolidin-1-ol | 532983-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-3-methoxymethoxypyrrolidin-1-ol
• 英文别名: Pyrrolidine, 1-hydroxy-3-(methoxymethoxy)-, (3S)-(9CI)；(3S)-1-hydroxy-3-(methoxymethoxy)pyrrolidine
• CAS: 532983-46-3
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: RBZVFWYEZFTKDG-LURJTMIESA-N

物化性质

• 沸点：
  220.1±33.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 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：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-methoxymethoxypyrrolidin-1-ol 在 manganese(IV) oxide 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.08h， 生成 (2R,3S)-3-Methoxymethoxy-1-trimethylsilanyloxy-pyrrolidine-2-carbonitrile
  参考文献：
  名称：

  A comparative study of the stereoselective addition of trimethylsilyl cyanide and diethylaluminum cyanide to chiral cyclic nitrones

  摘要：

  The mild cyanating agent trimethylsilyl cyanide adds with total stereo selectivity to alpha-alkoxy cyclic nitrones to afford the corresponding trans-hydroxyaminonitriles. The addition of Lewis acids to precomplexing the nitrones does not affect the stereoselectivity of these additions significantly. In all of the cases examined, excellent yields of diastereomerically homogeneous products were obtained. On the other hand, the use of diethylaluminum cyanide as cyanating agent leads to low diastereoselectivities. Both NMR studies and theoretical calculations show that whereas the addition of trimethylsilyl cyanide takes place through a concerted mechanism, in the addition of diethylaluminum cyanide, a complex is formed prior to the intramolecular delivery of the cyanide ion. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00832-7
• 作为产物：
  描述：

  (S)-1,4-di-O-mesyl-O-(methoxymethyl)-1,2,4-butanetriol 在 盐酸羟胺 、 三乙胺 作用下， 反应 4.0h， 以66%的产率得到(S)-3-methoxymethoxypyrrolidin-1-ol
  参考文献：
  名称：

  A comparative study of the stereoselective addition of trimethylsilyl cyanide and diethylaluminum cyanide to chiral cyclic nitrones

  摘要：

  The mild cyanating agent trimethylsilyl cyanide adds with total stereo selectivity to alpha-alkoxy cyclic nitrones to afford the corresponding trans-hydroxyaminonitriles. The addition of Lewis acids to precomplexing the nitrones does not affect the stereoselectivity of these additions significantly. In all of the cases examined, excellent yields of diastereomerically homogeneous products were obtained. On the other hand, the use of diethylaluminum cyanide as cyanating agent leads to low diastereoselectivities. Both NMR studies and theoretical calculations show that whereas the addition of trimethylsilyl cyanide takes place through a concerted mechanism, in the addition of diethylaluminum cyanide, a complex is formed prior to the intramolecular delivery of the cyanide ion. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00832-7

文献信息

• On the Virtue of Indium in Reduction Reactions. A Comparison of Reductions Mediated by Indium and Zinc: Is Indium Metal an Effective Catalyst for Zinc Induced Reductions?
  作者：Camilla Matassini、Marco Bonanni、Marco Marradi、Stefano Cicchi、Andrea Goti

  DOI：10.1002/ejic.201901081

  日期：2020.3.27

  Indium(0)‐mediated reductions have been reported for the transformation of several functional groups (imines, oximes, nitro groups, isoxazolidines, and conjugated alkenes, among others), prompted by the opportunity of performing the reactions in aqueous media and green conditions. We describe here the comparison of several reactions using indium or the less expensive zinc, carried out in order to evaluate

  据报道，由于在水性介质和绿色条件下进行反应的机会，铟（0）介导的还原作用可转化为多个官能团（亚胺，肟，硝基，异恶唑烷和共轭烯烃等）。我们在这里描述了使用铟或较便宜的锌进行的几种反应的比较，以评估铟金属带来的有效优势。我们发现必须强制使用In的某些反应，以及其他Zn效果相同甚至更好的反应。羟胺还原成相应的胺是唯一的还原方法，使用In可以提供比Zn更好的结果，并且在存在化学计量比的Zn的情况下也可以使用2-5 mol％In来应用有效的催化形式。
• Indium-Mediated Reduction of Hydroxylamines to Amines
  作者：Stefano Cicchi、Marco Bonanni、Francesca Cardona、Julia Revuelta、Andrea Goti

  DOI：10.1021/ol034434l

  日期：2003.5.1

  [GRAPHICS]A novel and simple procedure for reduction of hyproxylamines to the corresponding amines by means of indium powder in aqueous media is reported. Applicability to one-pot reactions and isoxazolidine N-O bond reduction is also demonstrated. A catalytic version of the process using 2-5% In in the presence of other metals (Zn, Al) has been successfully developed.
• A comparative study of the stereoselective addition of trimethylsilyl cyanide and diethylaluminum cyanide to chiral cyclic nitrones
  作者：Pedro Merino、Tomas Tejero、Julia Revuelta、Pilar Romero、Stefano Cicchi、Vanni Mannucci、Alberto Brandi、Andrea Goti

  DOI：10.1016/s0957-4166(02)00832-7

  日期：2003.2

  The mild cyanating agent trimethylsilyl cyanide adds with total stereo selectivity to alpha-alkoxy cyclic nitrones to afford the corresponding trans-hydroxyaminonitriles. The addition of Lewis acids to precomplexing the nitrones does not affect the stereoselectivity of these additions significantly. In all of the cases examined, excellent yields of diastereomerically homogeneous products were obtained. On the other hand, the use of diethylaluminum cyanide as cyanating agent leads to low diastereoselectivities. Both NMR studies and theoretical calculations show that whereas the addition of trimethylsilyl cyanide takes place through a concerted mechanism, in the addition of diethylaluminum cyanide, a complex is formed prior to the intramolecular delivery of the cyanide ion. (C) 2003 Elsevier Science Ltd. All rights reserved.