2-氮杂二环[2.2.1]庚烷-3-酮,4,7,7-三甲基-2-(2-甲基-1-羰基-2-丙烯基)-,(1S)- | 139278-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-氮杂二环[2.2.1]庚烷-3-酮,4,7,7-三甲基-2-(2-甲基-1-羰基-2-丙烯基)-,(1S)-
• 英文名称: (1R,4S)-3-Methacryloyl-1,7,7-trimethyl-3-azabicyclo<2.2.1>heptan-2-one
• 英文别名: (1S,4R)-4,7,7-trimethyl-2-(2-methylprop-2-enoyl)-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 139278-33-4
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: JKSSDJVRMZFYHP-ZANVPECISA-N

物化性质

• 沸点：
  323.3±15.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氮杂二环[2.2.1]庚烷-3-酮,4,7,7-三甲基-2-(2-甲基-1-羰基-2-丙烯基)-,(1S)- 在 lithium hydroxide 、 双氧水 、 甲基二氯化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (1R)-1-methylcyclohex-3-ene-1-carboxylic acid
  参考文献：
  名称：

  Toward the development of a general chiral auxiliary. 1. Preparation of a new class of camphor lactam imides and their application to the construction of quaternary centers via Diels-Alder cycloaddition.

  摘要：

  DOI：

  10.1021/ja00032a051
• 作为产物：
  描述：

  (1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one 、 甲基丙烯酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以28%的产率得到2-氮杂二环[2.2.1]庚烷-3-酮,4,7,7-三甲基-2-(2-甲基-1-羰基-2-丙烯基)-,(1S)-
  参考文献：
  名称：

  Palladium(II)-catalyzed asymmetric acetalization of alkenes

  摘要：

  The terminal olefinic carbon of N-methacryloyl-2-oxazolidinones is smoothly acetalized by alcohols in the presence of PdCl2 catalyst. The use of 4(S)-isopropyl-, phenyl-, and tert-butyl-2-oxazolidinones as the chiral auxiliary resulted in the formation of the corresponding (2'S)-acetals in 61, 80, and 95% de, respectively. Reductive removal of the auxiliary with LiAlH4 followed by deacetalization produced (R)-3-hydroxy-2-methylpropanal. The enantiomer of this compound, derived from 4(R)substituted oxazolidinones, served as a building block for synthesizing a 1 beta-methylcarbapenem precursor in high enantiomeric excess. In the acetalization of 3',3'-dideuteriated methacryloyl-4-isopropyloxaiolidinone with MeOH, one D-atom on the terminal olefinic carbon stereoselectively migrated to the chiral center in the product acetal. On the basis of this 1,2-hydride migration and the conformational preference of the methacryloyl moiety, the reaction pathway and the mechanism of the diastereoselection are discussed.

  DOI：

  10.1021/jo00124a032