(4aR,7aR)-5-[(1S,2R,4R)-2-(2,2-Dimethyl-propoxy)-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl]-3-methoxy-6-oxo-4a,5,6,7a-tetrahydro-oxazolo[5,4-e][1,3,4]oxadiazine-1-carboxylic acid methyl ester | 142618-83-5

• 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: (4aR,7aR)-5-[(1S,2R,4R)-2-(2,2-Dimethyl-propoxy)-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl]-3-methoxy-6-oxo-4a,5,6,7a-tetrahydro-oxazolo[5,4-e][1,3,4]oxadiazine-1-carboxylic acid methyl ester
• CAS: 142618-83-5
• 化学式: C₂₂H₃₃N₃O₈
• 分子量: 467.519
• InChiKey: YZUMFAKXUUTTNZ-ILRXCFRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  116.2
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  methyl (1S, 2R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptane-1-carboxylate 在 palladium on activated charcoal 盐酸 、 potassium permanganate 、 lithium aluminium tetrahydride 、 正丁基锂 、 氢气 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 52.58h， 生成 (4aR,7aR)-5-[(1S,2R,4R)-2-(2,2-Dimethyl-propoxy)-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carbonyl]-3-methoxy-6-oxo-4a,5,6,7a-tetrahydro-oxazolo[5,4-e][1,3,4]oxadiazine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0

文献信息

• Versatile routes to chiral 4-substituted 2-oxazolidinones and .ALPHA.-amino acids. Use of chiron, (4+2) cycloadducts of dialkyl azodicarboxylates and 2-oxazolones.
  作者：Hirofumi MATSUNAGA、Tadao ISHIZUKA、Nobuhiro MARUBAYASHI、Takehisa KUNIEDA

  DOI：10.1248/cpb.40.1077

  日期：——

  The thermal reaction of 3-[(1S)-2-alkoxyl-1-apocamphanecarbonyl]-2-oxazolones with dialkyl azodicarboxylates results in exclusive formation of [4+2] type cycloadducts with moderate levels of diastereofacial selection, which serve as versatile chiral synthons for a wide variety of 4-alkyl and 4-aryl-2-oxazolidinones as well as α-amino acids.

  3-[(1S)-2-烷氧基-1-阿波伞烷酮]-2-噁唑酮与二烷基偶氮二甲酸酯的热反应导致专一性形成[4+2]型环加成物，具有中等程度的非对映面选择性，这些产物作为多功能的手性合成前体，可用于合成多种4-烷基和4-芳基-2-噁唑啉酮以及α-氨基酸。