(5S,6R,1'R,2'R,4'R)-3,4,5,6-tetrahydro-5-methyl-4-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-6-phenyl-3-propionyl-2H-1,3,4-oxadiazin-2-one | 850218-37-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S,6R,1'R,2'R,4'R)-3,4,5,6-tetrahydro-5-methyl-4-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-6-phenyl-3-propionyl-2H-1,3,4-oxadiazin-2-one
• 英文别名: (5S,6R)-5-methyl-6-phenyl-3-propanoyl-4-[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-1,3,4-oxadiazinan-2-one
• CAS: 850218-37-0
• 化学式: C₂₃H₃₂N₂O₃
• 分子量: 384.519
• InChiKey: MKBVFACWIGHRFS-QPGHYZHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-萘甲醛 、 (5S,6R,1'R,2'R,4'R)-3,4,5,6-tetrahydro-5-methyl-4-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-6-phenyl-3-propionyl-2H-1,3,4-oxadiazin-2-one 在 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(5S,6R,1'R,2'R,4'R,2''S,3''S)-3,4,5,6-tetrahydro-3-(3-hydroxy-2-methyl-3-naphthalen-2-yl-propionyl)-5-methyl-6-phenyl-4-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-2H-1,3,4-oxadiazin-2-one
  参考文献：
  名称：

  Synthesis, X-ray crystallography and computational studies concerning an oxadiazinone derived from d-camphor: a structural limitation of oxadiazinones as chiral auxiliaries

  摘要：

  A camphor-based oxadiazinone was prepared by reaction of the N-nitroimine of D-camphor with (1R,2S)-norephedrine; the reduction of the resultant imine; N-nitrosation of the amine; reduction to the corresponding hydrazine and cyclization. The conformational behaviour of oxadiazinone 7 was modeled in the gas and solution phases using the semiempirical AM1 method and density functional theory. Application of the oxadiazinone in the titanium mediated asymmetric aldol reaction provided the highly diastereoselective formation of the expected syn-adducts 8a-d as evidenced by single crystal X-ray diffraction analysis. Attempts to remove the oxadiazinone auxiliary using acidic or basic conditions failed to yield the expected beta-hydroxyacid in significant yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.020
• 作为产物：
  描述：

  (1R,1'R,2S,2'R,4'R)-2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl-N-nitrosoamino)-1-phenylpropan-1-ol 在 lithium aluminium tetrahydride 、 lithium hydride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 (5S,6R,1'R,2'R,4'R)-3,4,5,6-tetrahydro-5-methyl-4-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-6-phenyl-3-propionyl-2H-1,3,4-oxadiazin-2-one
  参考文献：
  名称：

  Synthesis, X-ray crystallography and computational studies concerning an oxadiazinone derived from d-camphor: a structural limitation of oxadiazinones as chiral auxiliaries

  摘要：

  A camphor-based oxadiazinone was prepared by reaction of the N-nitroimine of D-camphor with (1R,2S)-norephedrine; the reduction of the resultant imine; N-nitrosation of the amine; reduction to the corresponding hydrazine and cyclization. The conformational behaviour of oxadiazinone 7 was modeled in the gas and solution phases using the semiempirical AM1 method and density functional theory. Application of the oxadiazinone in the titanium mediated asymmetric aldol reaction provided the highly diastereoselective formation of the expected syn-adducts 8a-d as evidenced by single crystal X-ray diffraction analysis. Attempts to remove the oxadiazinone auxiliary using acidic or basic conditions failed to yield the expected beta-hydroxyacid in significant yield. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.020

文献信息

• Synthesis, X-ray crystallography and computational studies concerning an oxadiazinone derived from d-camphor: a structural limitation of oxadiazinones as chiral auxiliaries
  作者：Michael D. Squire、Ryan A. Davis、Karah A. Chianakas、Gregory M. Ferrence、Jean M. Standard、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2005.01.020

  日期：2005.3

  A camphor-based oxadiazinone was prepared by reaction of the N-nitroimine of D-camphor with (1R,2S)-norephedrine; the reduction of the resultant imine; N-nitrosation of the amine; reduction to the corresponding hydrazine and cyclization. The conformational behaviour of oxadiazinone 7 was modeled in the gas and solution phases using the semiempirical AM1 method and density functional theory. Application of the oxadiazinone in the titanium mediated asymmetric aldol reaction provided the highly diastereoselective formation of the expected syn-adducts 8a-d as evidenced by single crystal X-ray diffraction analysis. Attempts to remove the oxadiazinone auxiliary using acidic or basic conditions failed to yield the expected beta-hydroxyacid in significant yield. (C) 2005 Elsevier Ltd. All rights reserved.