(3S,6S,7S,9aS)-3-(azidomethyl)-6-(3-bromophenyl)-7-methyl-hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one | 936445-25-9

• 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: (3S,6S,7S,9aS)-3-(azidomethyl)-6-(3-bromophenyl)-7-methyl-hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one
• 英文别名: (3S,6S,7S,9aS)-3-(azidomethyl)-6-(3-bromophenyl)-7-methyl-4,6,7,8,9,9a-hexahydro-3H-pyrido[2,1-c][1,4]oxazin-1-one
• CAS: 936445-25-9
• 化学式: C₁₆H₁₉BrN₄O₂
• 分子量: 379.256
• InChiKey: XUFVYAFOSJOQJV-PUPMMZHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6S,7S,9aS)-3-(azidomethyl)-6-(3-bromophenyl)-7-methyl-hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one 、 4-氯苯甲醛 在 三苯基膦 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以50%的产率得到(4S,7S,8S,10aS)-2-(4-chlorobenzyl)-7-(3-bromophenyl)-4-hydroxy-8-methyl-octahydropyrido[1,2-a][1,4]diazepin-1(7H)-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-(3-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 22.0h， 生成 (3S,6S,7S,9aS)-3-(azidomethyl)-6-(3-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

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.