(E)-(1S,2S,4R)-2-(2-methoxyethenyl)-1-(phenylmethoxymethyl)-bicyclo[2.2.2]oct-5-ene | 1195789-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(1S,2S,4R)-2-(2-methoxyethenyl)-1-(phenylmethoxymethyl)-bicyclo[2.2.2]oct-5-ene
• 英文别名: (1S,4R,6S)-6-[(E)-2-methoxyethenyl]-1-(phenylmethoxymethyl)bicyclo[2.2.2]oct-2-ene
• CAS: 1195789-92-4
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: NYMCJRZOALIDSJ-FLXHGYJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,2R,4R)-1-(phenylmethoxymethyl)bicyclo[2.2.2]oct-5-ene-2-carboxaldehyde 、 (甲氧基甲基)二苯基磷氧 在 lithium diisopropyl amide 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.17h， 生成 (Z)-(1S,2S,4R)-2-(2-methoxyethenyl)-1-(phenylmethoxymethyl)-bicyclo[2.2.2]oct-5-ene 、 (E)-(1S,2S,4R)-2-(2-methoxyethenyl)-1-(phenylmethoxymethyl)-bicyclo[2.2.2]oct-5-ene
  参考文献：
  名称：

  Synthesis and Antibacterial Properties of (−)-nor-Platencin

  摘要：

  An asymmetric Diels-Alder reaction between acrolein and 1-benzyloxymethyl-1,3-cyclohexadiene affords a bicyclic aldehyde that was elaborated in 11 steps to nor-platencin. nor-Platencin is 4-16 times less active than platencin against several resistant strains of Staphylococcus aureus, macrolide-resistant Enterococcus faecalis, and vancomycin-resistant Enterococcus faecium.

  DOI：

  10.1021/ol902194q

文献信息

• Synthesis and Antibacterial Properties of (−)-<i>nor</i>-Platencin
  作者：Olga V. Barykina、Kerri L. Rossi、Michael J. Rybak、Barry B. Snider

  DOI：10.1021/ol902194q

  日期：2009.11.19

  An asymmetric Diels-Alder reaction between acrolein and 1-benzyloxymethyl-1,3-cyclohexadiene affords a bicyclic aldehyde that was elaborated in 11 steps to nor-platencin. nor-Platencin is 4-16 times less active than platencin against several resistant strains of Staphylococcus aureus, macrolide-resistant Enterococcus faecalis, and vancomycin-resistant Enterococcus faecium.