(3S)-3-tert-Butoxy-N-hydroxypyrrolidine | 167971-77-9

• 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: (3S)-3-tert-Butoxy-N-hydroxypyrrolidine
• 英文别名: 3(S)-tert-butoxy-N-hydroxypyrrolidine；Pyrrolidine, 3-(1,1-dimethylethoxy)-1-hydroxy-, (3S)-；(3S)-1-hydroxy-3-[(2-methylpropan-2-yl)oxy]pyrrolidine
• CAS: 167971-77-9
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: XCCJPVWLITUZMU-ZETCQYMHSA-N

物化性质

• 沸点：
  230.2±29.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 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：

  (3S)-3-tert-Butoxy-N-hydroxypyrrolidine 在 lithium aluminium deuteride 、 mercury(II) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (3S,2R) 2-Deuterio-3-tert-butoxy-N-hydroxypyrrolidine
  参考文献：
  名称：

  A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine

  摘要：

  The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.

  DOI：

  10.1021/jo00120a016
• 作为产物：
  描述：

  (2S)-2-tert-Butoxy-1,4-butanediol 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 (3S)-3-tert-Butoxy-N-hydroxypyrrolidine
  参考文献：
  名称：

  A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine

  摘要：

  The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.

  DOI：

  10.1021/jo00120a016

文献信息

• Oxidation of <i>N</i>,<i>N</i>-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents
  作者：Camilla Matassini、Camilla Parmeggiani、Francesca Cardona、Andrea Goti

  DOI：10.1021/acs.orglett.5b02029

  日期：2015.8.21

  Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high efficiency and regioselectivity, highlighting IBX as the reagent of choice for preparation of aldonitrones from nonsymmetric hydroxylamines. Evidence for

  高价碘化合物是将N，N-二取代的羟胺氧化为相应的硝酮的可行试剂，而IBX表现最佳。该方法非常简单且易于使用，可为目标化合物提供高效和区域选择性，突出了IBX作为从非对称羟胺制备醛酮的选择试剂。已经收集了涉及氮与碘配位的机理的证据。
• Oxidation ofN,N-Disubstituted Hydroxylamines to Nitrones with Hydrogen Peroxide Catalyzed by Polymer-Supported Methylrhenium Trioxide Systems
  作者：Raffaele Saladino、Veronica Neri、Francesca Cardona、Andrea Goti

  DOI：10.1002/adsc.200303223

  日期：2004.5

  Poly(4-vinylpyridine)/methylrhenium trioxide (MTO) compounds IIII and microencapsulated polystyrene/MTO systems IVV are efficient catalysts for the oxidation of secondary hydroxylamines to the corresponding nitrones with H2O2. Complete conversions of substrates and quantitative yields of products are obtained under environmentally friendly experimental conditions and with the use of simple work-up

  聚（4-乙烯基吡啶）/三氧化二甲基methyl（MTO）化合物IIII和微囊化的聚苯乙烯/ MTO系统IVV是将仲羟胺氧化为相应的H 2 O 2硝酮的有效催化剂。在环境友好的实验条件下并使用简单的后处理程序即可获得底物的完全转化和定量的产品收率。对称取代的羟胺，以及非对称的3-取代和2-取代的羟基吡咯烷酮，用于生物碱和生物活性同类物合成的硝酮的前体，被认为是底物。该非均相催化剂在反应条件下是稳定的，并且可以被回收和再循环至少五次而没有任何明显的效率损失。
• Inexpensive and Environmentally Friendly Oxidation of Hydroxylamines to Nitrones with Bleach
  作者：Stefano Cicchi、Massimo Corsi、Andrea Goti

  DOI：10.1021/jo990417r

  日期：1999.9.1
• Manganese dioxide oxidation of hydroxylamines to nitrones
  作者：Stefano Cicchi、Marco Marradi、Andrea Goti、Alberto Brandi

  DOI：10.1016/s0040-4039(01)01222-9

  日期：2001.9

  Several structurally differentiated N,N-dialkylhydroxylamines were oxidised to the corresponding nitrones using MnO2. Manganese dioxide revealed an efficient and mild reagent for oxidation of hydroxylamines, showing a level of regioselectivity comparable to HgO. Its non-toxicity makes MnO2 the reagent of choice for replacing HgO in this oxidation. (C) 2001 Elsevier Science Ltd. All rights reserved.