(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyrrole 1-oxide | 150931-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyrrole 1-oxide
• 英文别名: tert-butyl-dimethyl-[[(4R)-1-oxido-3,4-dihydro-2H-pyrrol-1-ium-4-yl]oxy]silane
• CAS: 150931-63-8
• 化学式: C₁₀H₂₁NO₂Si
• 分子量: 215.368
• InChiKey: RADWYHZXLQTEOW-SECBINFHSA-N

物化性质

• 沸点：
  307.4±35.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyrrole 1-oxide 在 palladium on activated charcoal 氢气 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxycarbonylmethyl-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides — chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone

  摘要：

  Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00333-5
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 palladium on activated charcoal sodium tungstate 、 四丁基氯化铵 、 氢气 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyrrole 1-oxide
  参考文献：
  名称：

  Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides — chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone

  摘要：

  Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00333-5

文献信息

• Regioselective Synthesis of Nitrones by Decarboxylative Oxidation of<i>N</i>-Alkyl-<i>α</i>-amino Acids and Application to the Synthesis of 1-Azabicyclic Alkaloids
  作者：Hiroaki Ohtake、Yasushi Imada、Shun-Ichi Murahashi

  DOI：10.1246/bcsj.72.2737

  日期：1999.12

  were prepared by catalytic oxidation of the corresponding chiral pyrrolidines in a regioselective manner. These chiral cyclic nitrones, 17 and 45 are versatile intermediates for the synthesis of optically active nitrogen heterocycles, since stereoselective additions of carbon nucleophiles to these chiral nitrones can be readily performed. Typically, ZnI2-mediated addition of ketene t-butyldimethylsilyl

  在相转移条件下用 30% H2O2 溶液钨酸盐催化氧化 N-烷基-α-氨基酸，区域选择性地以良好的产率得到硝酮。使用该方法，实现了（R）-和（S）-4-（叔丁基二甲基甲硅烷氧基）-1-吡咯啉N-氧化物（（R）-17a和（S）-17a）的立体发散合成。此外，(R)-和(S)-3-(叔丁基二甲基甲硅烷氧基)-1-吡咯啉N-氧化物((R)-45和(S)-45)是通过相应手性吡咯烷的催化氧化制备的区域选择性方式。这些手性环状硝酮 17 和 45 是合成光学活性氮杂环的通用中间体，因为可以很容易地将碳亲核试剂立体选择性加成到这些手性硝酮上。通常，ZnI2 介导的乙烯酮叔丁基二甲基甲硅烷基甲基缩醛 (29a) 与 (R)-17a 的加成得到顺式加合物，(2R,4R)-[1,4-双(叔丁基二甲基甲硅烷氧基)吡咯烷-2-基]乙酸甲酯(cis-30)。相比之下，将乙炔锂 34 添加到硝酮 (R)-17a 中得到
• Tungstate-Catalyzed Decarboxylative Oxidation of N-Alkyl-.alpha.-amino Acids: An Efficient Method for Regioselective Synthesis of Nitrones
  作者：Shun-Ichi Murahashi、Yasushi Imada、Hiroaki Ohtake

  DOI：10.1021/jo00100a016

  日期：1994.10

  The tungstate-catalyzed oxidation of N-alkyl-alpha-amino acids with hydrogen peroxide under phase-transfer conditions gives the corresponding nitrones in satisfactory yield.
• Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides — chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone
  作者：Shun-Ichi Murahashi、Hiroaki Ohtake、Yasushi Imada

  DOI：10.1016/s0040-4039(98)00333-5

  日期：1998.4

  Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.