4(S),5(R)-5-acetyl-4-(4(S)-2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,5-dihydroisoxazole | 181635-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4(S),5(R)-5-acetyl-4-(4(S)-2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,5-dihydroisoxazole
• 英文别名: 1-[(4S,5R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4,5-dihydro-1,2-oxazol-5-yl]ethanone
• CAS: 181635-95-0
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: AKZMKYMTSOIHQA-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4(S),5(R)-5-acetyl-4-(4(S)-2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,5-dihydroisoxazole 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以55%的产率得到
  参考文献：
  名称：

  Enantiomerically pure isoxazolines by stereoselective 1,3-dipolar cycloaddition of silyl nitronates

  摘要：

  The cycloaddition reactions of in situ generated silyl nitronates 3 to chiral enone 1a or enoate 1b proceed with high stereoselectivity to give enantiomerically pure N-silyloxyisoxazolidines 4, which can easily be transformed into Delta(2)-isoxazolines 5. Based on an X-ray analysis the major diastereomers were assigned as the syn-derivatives, thus differing from diastereofacial selectivity found with nitrile oxides. The base-catalyzed ring-opening reaction of isoxazoline 5a affords the chiral beta-hydroxy nitrile 6, which was cyclized to the sugar-lire tetrahydrofuran 7. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00250-9
• 作为产物：
  描述：

  (3E)-4-[(4S)-2,2-dimethyl(1,3-dioxolan-4-yl)]but-3-en-2-one 在 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 75.0h， 生成 4(S),5(R)-5-acetyl-4-(4(S)-2,2-dimethyl-[1,3]-dioxolan-4-yl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  Enantiomerically pure isoxazolines by stereoselective 1,3-dipolar cycloaddition of silyl nitronates

  摘要：

  The cycloaddition reactions of in situ generated silyl nitronates 3 to chiral enone 1a or enoate 1b proceed with high stereoselectivity to give enantiomerically pure N-silyloxyisoxazolidines 4, which can easily be transformed into Delta(2)-isoxazolines 5. Based on an X-ray analysis the major diastereomers were assigned as the syn-derivatives, thus differing from diastereofacial selectivity found with nitrile oxides. The base-catalyzed ring-opening reaction of isoxazoline 5a affords the chiral beta-hydroxy nitrile 6, which was cyclized to the sugar-lire tetrahydrofuran 7. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00250-9

文献信息

• Enantiomerically pure isoxazolines by stereoselective 1,3-dipolar cycloaddition of silyl nitronates
  作者：Guido Galley、Peter G. Jones、Michael Pätzel

  DOI：10.1016/0957-4166(96)00250-9

  日期：1996.7

  The cycloaddition reactions of in situ generated silyl nitronates 3 to chiral enone 1a or enoate 1b proceed with high stereoselectivity to give enantiomerically pure N-silyloxyisoxazolidines 4, which can easily be transformed into Delta(2)-isoxazolines 5. Based on an X-ray analysis the major diastereomers were assigned as the syn-derivatives, thus differing from diastereofacial selectivity found with nitrile oxides. The base-catalyzed ring-opening reaction of isoxazoline 5a affords the chiral beta-hydroxy nitrile 6, which was cyclized to the sugar-lire tetrahydrofuran 7. Copyright (C) 1996 Elsevier Science Ltd