(2R,5R,6S)-6-N-benzylamino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one | 199436-23-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,5R,6S)-6-N-benzylamino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one
• 英文别名: (3R,7s,7as)-7-(benzylamino)-3-phenyl-dihydropyrrolo[1,2-c]oxazol-5(1h,3h,6h)-one；(3R,7S,7aS)-7-(benzylamino)-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
• CAS: 199436-23-2
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: ACZSPODZOUYPDW-YQVWRLOYSA-N

物化性质

• 沸点：
  511.4±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R,6S)-6-N-benzylamino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (4S,5S)-4-N-benzylamino-5-hydroxymethylpyrrolidin-2-one
  参考文献：
  名称：

  Stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and (7S,8R)-7-N-benzylaminopyrrolizidin-3-one

  摘要：

  The highly stereoselective synthesis of of (2S,3S)-3N-benzylaminoprolinol and derivatives involved the conjugate addition of N-benzylamine to alpha,beta-unsaturated lactam 2. Wittig-Horner reactions with 1-acetyl-3-N-acetyl-N-benzylaminoprolinal provided a simple access to (7S,8R)-7-N-benzylaminopyrrolizidin-3-one. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10749-3
• 作为产物：
  描述：

  (2R,5S,6S)-6-(N-benzyl-N-hydroxy)amino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one 在 titanium(III) chloride 作用下， 以80%的产率得到(2R,5R,6S)-6-N-benzylamino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one
  参考文献：
  名称：

  Stereocontrolled Synthesis of Enantiopure Substituted 4-Aminopyrrolidin-2-ones

  摘要：

  The highly diastereoselective conjugate addition of N-benzylhydroxylamine and benzylamine to alpha,beta-unsaturated lactam 3 provided an efficient entry to enantiopure (4S,5S)-4-amino-5-hydroxymethylpyrrolidin-2-ones. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10216-7

文献信息

• Intramolecular Mitsunobu reaction in the regio- and stereoselective synthesis of cis-4,5-disubstituted piperidin-2-ones
  作者：Nicole Langlois、Olivier Calvez

  DOI：10.1016/s0040-4039(00)01461-1

  日期：2000.10

  Enantiopure cis-4,5-disubstituted piperidin-2-ones were synthesized through the cyclization of O-benzyl hydroxamates under Mitsunobu conditions, followed by samarium diiodide reduction.

  通过在Mitsunobu条件下将O-苄基异羟肟酸酯环化，然后还原二碘化sa，合成了对映体纯的顺式-4,5-二取代的哌啶-2-酮。
• A Short and Efficient Synthesis of (3<i>S</i>,4<i>S</i>)-1-Benzyl-4-<i>N</i>-Benzylamino-3-Hydroxypiperidine
  作者：Nicole Langlois、Olivier Calvez

  DOI：10.1080/00397919808004482

  日期：1998.12

  (3S,4S)-1-Benzyl-4-N-benzylamino-3-hydroxypiperidine 1 was efficiently synthesized from (S)-pyroglutaminol.

  (3S,4S)-1-苯甲基-4-N-苯甲基氨基-3-羟基哌啶1由(S)-吡咯谷氨酰醇高效合成。
• Stereocontrolled Synthesis of Enantiopure Substituted 4-Aminopyrrolidin-2-ones
  作者：Nicole Langlois、Olivier Calvez、Marie-Odile Radom

  DOI：10.1016/s0040-4039(97)10216-7

  日期：1997.11

  The highly diastereoselective conjugate addition of N-benzylhydroxylamine and benzylamine to alpha,beta-unsaturated lactam 3 provided an efficient entry to enantiopure (4S,5S)-4-amino-5-hydroxymethylpyrrolidin-2-ones. (C) 1997 Elsevier Science Ltd.
• Stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and (7S,8R)-7-N-benzylaminopyrrolizidin-3-one
  作者：Nicole Langlois、Marie-Odile Radom

  DOI：10.1016/s0040-4039(97)10749-3

  日期：1998.2

  The highly stereoselective synthesis of of (2S,3S)-3N-benzylaminoprolinol and derivatives involved the conjugate addition of N-benzylamine to alpha,beta-unsaturated lactam 2. Wittig-Horner reactions with 1-acetyl-3-N-acetyl-N-benzylaminoprolinal provided a simple access to (7S,8R)-7-N-benzylaminopyrrolizidin-3-one. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.