methyl (2S,5S,6S)-1-((S)-3-azido-2-hydroxypropyl)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate | 936445-15-7

• 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: methyl (2S,5S,6S)-1-((S)-3-azido-2-hydroxypropyl)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate
• 英文别名: methyl (2S,5S,6S)-1-[(2S)-3-azido-2-hydroxypropyl]-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate
• CAS: 936445-15-7
• 化学式: C₁₇H₂₃BrN₄O₃
• 分子量: 411.299
• InChiKey: TUFXQPOBQPSSNI-MWNCTCPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,5S,6S)-1-((S)-3-azido-2-hydroxypropyl)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 10.0h， 以92%的产率得到(3S,6S,7S,9aS)-3-(azidomethyl)-6-(4-bromophenyl)-7-methyl-hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one
  参考文献：
  名称：

  Stereochemical and Skeletal Diversity Employing Pipecolate Ester Scaffolds

  摘要：

  [GRAPHICS]The stereocontrolled synthesis of pyridooxazinones by Mg(OTf)(2)-promoted epoxide ring-opening with use of chiral pipecolates as nucleophiles is described. Pyridooxazinone products derived from azido-epoxides can be further rearranged to seven-membered pyridodiazepinones by azide reduction. The sequence of functional group interconversions generates diversity through topological and stereochemical variation.

  DOI：

  10.1021/ol070321g
• 作为产物：
  描述：

  methyl (2S,5S,6S)-6-(4-bromophenyl)-1-(2,2,2-trifluoroacetyl)-1,2,5,6-tetrahydro-5-methylpyridine-2-carboxylate 在 platinum(IV) oxide 氢气 、 magnesium triflate 、 sodium nitrite 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 29.0h， 生成 methyl (2S,5S,6S)-1-((S)-3-azido-2-hydroxypropyl)-6-(4-bromophenyl)-5-methylpiperidine-2-carboxylate
  参考文献：
  名称：

  Stereochemical and Skeletal Diversity Employing Pipecolate Ester Scaffolds

  摘要：

  [GRAPHICS]The stereocontrolled synthesis of pyridooxazinones by Mg(OTf)(2)-promoted epoxide ring-opening with use of chiral pipecolates as nucleophiles is described. Pyridooxazinone products derived from azido-epoxides can be further rearranged to seven-membered pyridodiazepinones by azide reduction. The sequence of functional group interconversions generates diversity through topological and stereochemical variation.

  DOI：

  10.1021/ol070321g

文献信息

• Stereochemical and Skeletal Diversity Employing Pipecolate Ester Scaffolds
  作者：Yu Chen、John A. Porco,、James S. Panek

  DOI：10.1021/ol070321g

  日期：2007.4.1

  [GRAPHICS]The stereocontrolled synthesis of pyridooxazinones by Mg(OTf)(2)-promoted epoxide ring-opening with use of chiral pipecolates as nucleophiles is described. Pyridooxazinone products derived from azido-epoxides can be further rearranged to seven-membered pyridodiazepinones by azide reduction. The sequence of functional group interconversions generates diversity through topological and stereochemical variation.