(Z)-N-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methylidene}benzylamine N-oxide | 243983-11-1

• 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: (Z)-N-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methylidene}benzylamine N-oxide
• 英文别名: N-benzyl-1-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]methanimine oxide
• CAS: 243983-11-1；1050549-68-2
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: JIUQPCYGCGOSCH-LUJRCDHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methylidene}benzylamine N-oxide 在 copper diacetate 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 (3S)-3-benzylamino-3-[(2S)-1-(tert-butoxycarbonylamino)pyrrolidin-2-yl]-1-propene
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.

  DOI：

  10.1080/00397910008087449
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 、 N-苄基羟胺 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以80%的产率得到(Z)-N-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methylidene}benzylamine N-oxide
  参考文献：
  名称：

  通过甲硅烷基三氟甲磺酸酯促进的亚磷酸二乙酯加成到手性 N-苄基硝酮中，一种新的、方便的非对映选择性合成 α-（羟基氨基）膦酸酯和 α-氨基膦酸酯

  摘要：

  已经开发了一种合成 α-氨基膦酸酯的有效方法，利用叔丁基二甲基甲硅烷基三氟甲磺酸酯活化亚磷酸二乙酯与衍生自手性 α-烷氧基和 α-（Boc-氨基）醛的 N-苄基硝酮的加成。立体选择性碳-磷键形成反应顺利进行，得到 α-（羟基氨基）膦酸酯中间体作为主要加合物，随后通过常规还原方法将其转化为相应的多羟基化 α-氨基-和 α,β-二氨基膦酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200200698

文献信息

• Highly diastereoselective nucleophilic addition of organometallic reagents to 2-pyrrolidinyl nitrones: a semiempirical approach
  作者：Pedro Merino、Santiago Franco、Jose M. Gascon、Francisco L. Merchan、Tomas Tejero

  DOI：10.1016/s0957-4166(99)00203-7

  日期：1999.5

  2-Pyrrolidinyl nitrones 1 and 2 derived from l-proline and trans-4-hydroxy-l-proline, respectively, undergo nucleophilic additions of Grignard reagents and organolithium compounds with high syn selectivity, to yield enantiomerically pure pyrrolidinyl benzyl hydroxylamines. A rationale for the observed stereoselectivity based on semiempirical calculations is presented.

  分别衍生自1-脯氨酸和反式-4-羟基-1-脯氨酸的2-吡咯烷基亚硝基1和2经过格氏试剂和有机锂化合物的亲核加成，具有高的顺式选择性，从而得到对映体纯的吡咯烷基苄基羟胺。提出了基于半经验计算的观察到的立体选择性的原理。
• O -Silyl triflate-promoted addition of diethyl phosphite to chiral aldonitrones. A rapid access to complex α-amino phosphonates and their N -hydroxy derivatives
  作者：Carmela De Risi、Alessandro Dondoni、Daniela Perrone、Gian Piero Pollini

  DOI：10.1016/s0040-4039(01)00363-x

  日期：2001.4

  The addition reaction of diethyl phosphite to O-silylated N-benzyl nitrones derived from chiral alpha -alkoxy and N-Boc alpha -amino aldehydes has been studied as a stereoselective carbon-phosphorus bond forming process for the synthesis of polyhydroxylated alpha -amino and alpha,beta -diamino phosphonates. Key intermediates are the corresponding N-hydroxy alpha -amino phosphonates. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A New and Expedient Diastereoselective Synthesis of α-(Hydroxyamino)phosphonates and α-Aminophosphonates by Silyl Triflate Promoted Diethyl Phosphite Addition to Chiral N-Benzyl Nitrones
  作者：Carmela De Risi、Daniela Perrone、Alessandro Dondoni、Gian Piero Pollini、Valerio Bertolasi

  DOI：10.1002/ejoc.200200698

  日期：2003.5

  efficient methodology for the synthesis of α-aminophosphonates has been developed taking advantage of the tert-butyldimethylsilyl triflate activated addition of diethyl phosphite to N-benzyl nitrones derived from chiral α-alkoxy and α-(Boc-amino) aldehydes. The stereoselective carbon− phosphorus bond-forming reaction proceeded smoothly to give α-(hydroxyamino)phosphonate intermediates as the primary

  已经开发了一种合成 α-氨基膦酸酯的有效方法，利用叔丁基二甲基甲硅烷基三氟甲磺酸酯活化亚磷酸二乙酯与衍生自手性 α-烷氧基和 α-（Boc-氨基）醛的 N-苄基硝酮的加成。立体选择性碳-磷键形成反应顺利进行，得到 α-（羟基氨基）膦酸酯中间体作为主要加合物，随后通过常规还原方法将其转化为相应的多羟基化 α-氨基-和 α,β-二氨基膦酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines
  作者：Pedro Merino、Sonia Anoro、Santiago Franco、Jose M. Gascon、Victor Martin、Francisco L. Merchan、Julia Revuelta、Tomas Tejero、Victoria Tuñon

  DOI：10.1080/00397910008087449

  日期：2000.8

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.