N-(butyl-isosorbide)bicyclo[2.2.1]hept-5-ene-2,3-di-exo-carboximide | 385806-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: N-(butyl-isosorbide)bicyclo[2.2.1]hept-5-ene-2,3-di-exo-carboximide
• 英文别名: (1R,2R,6S,7S)-4-[4-[[(3R,3aR,6S,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]butyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 385806-10-0
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: VUDASCKDFBMOBW-OFZWUMGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[2-(3-bromo-propyl)-phenyl]-acrylic acid 、 N-(butyl-isosorbide)bicyclo[2.2.1]hept-5-ene-2,3-di-exo-carboximide 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(E)-3-[2-(3-Bromo-propyl)-phenyl]-acrylic acid (3R,3aR,6S,6aR)-6-[4-((1R,2R,6S,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-butoxy]-hexahydro-furo[3,2-b]furan-3-yl ester
  参考文献：
  名称：

  Highly Diastereoselective Radical Cyclizations on Soluble Ring Opening Metathesis Supports

  摘要：

  [GRAPHICS]This study represents the first examples of stereoselective radical cyclizations on soluble supports. A stereocontrol element consisting of a polymer-imbedded (+)-isosorbide chiral auxiliary was used in each monomer subunit. A survey of various Lewis acids was also examined. The best results gave very high distereoselectivites of > 100:1 in a hepa-1,3-dienenyl radical cyclization using zinc chloride as a Lewis acid.

  DOI：

  10.1021/ol016855d
• 作为产物：
  描述：

  (3aR,4R,7S,7aS)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 、 正戊烷 为溶剂， 反应 15.33h， 生成 N-(butyl-isosorbide)bicyclo[2.2.1]hept-5-ene-2,3-di-exo-carboximide
  参考文献：
  名称：

  Highly Diastereoselective Radical Cyclizations on Soluble Ring Opening Metathesis Supports

  摘要：

  [GRAPHICS]This study represents the first examples of stereoselective radical cyclizations on soluble supports. A stereocontrol element consisting of a polymer-imbedded (+)-isosorbide chiral auxiliary was used in each monomer subunit. A survey of various Lewis acids was also examined. The best results gave very high distereoselectivites of > 100:1 in a hepa-1,3-dienenyl radical cyclization using zinc chloride as a Lewis acid.

  DOI：

  10.1021/ol016855d