(1S,13R)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,11,14(22),15,17(21)-heptaene | 1569900-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (1S,13R)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,11,14(22),15,17(21)-heptaene
• CAS: 1569900-65-7
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: AHTRQQDDQGEFLA-XIKOKIGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,13R)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,11,14(22),15,17(21)-heptaene 、 氯甲酸苄酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以78%的产率得到benzyl (1S,13R)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,11,14(22),15,17(21)-heptaene-24-carboxylate
  参考文献：
  名称：

  对映选择性钯催化的氮杂苯并降冰片二烯与2-碘代苯甲酸甲酯的开环反应：有效地获得顺式-二氢苯并[ c ]菲啶酮

  摘要：

  AbstractThe palladium‐catalyzed asymmetric ring‐opening (ARO) reaction of azabenzonorbornadienes with iodobenzoate derivatives was realized by using chiral spirophosphine ligands with zinc powder as a reducing reagent. Various enantiomerically enriched cis‐dihydrobenzo[c]phenanthridinones, the core structure of numerous chiral natural products, were prepared by the ARO reaction and tandem amidation from easily obtained starting materials with favorable enantioselectivity (up to 86% ee) under mild reaction conditions. The present palladium‐catalyzed ARO reaction avoids the direct use of organometallic reagents, enables tandem cyclization, and thus improves synthetic efficiency. The formal total synthesis of a chiral natural product, (+)‐chelidonine, was accomplished with the ARO reaction as a key step, which demonstrates the potential synthetic applications of the present methodology.magnified image

  DOI：

  10.1002/adsc.201300452
• 作为产物：
  描述：

  7,8-methylenedioxy-13,14-cis-dihydrobenzodioxolebenzo[c]phenanthridin-6-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以97%的产率得到(1S,13R)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,11,14(22),15,17(21)-heptaene
  参考文献：
  名称：

  对映选择性钯催化的氮杂苯并降冰片二烯与2-碘代苯甲酸甲酯的开环反应：有效地获得顺式-二氢苯并[ c ]菲啶酮

  摘要：

  AbstractThe palladium‐catalyzed asymmetric ring‐opening (ARO) reaction of azabenzonorbornadienes with iodobenzoate derivatives was realized by using chiral spirophosphine ligands with zinc powder as a reducing reagent. Various enantiomerically enriched cis‐dihydrobenzo[c]phenanthridinones, the core structure of numerous chiral natural products, were prepared by the ARO reaction and tandem amidation from easily obtained starting materials with favorable enantioselectivity (up to 86% ee) under mild reaction conditions. The present palladium‐catalyzed ARO reaction avoids the direct use of organometallic reagents, enables tandem cyclization, and thus improves synthetic efficiency. The formal total synthesis of a chiral natural product, (+)‐chelidonine, was accomplished with the ARO reaction as a key step, which demonstrates the potential synthetic applications of the present methodology.magnified image

  DOI：

  10.1002/adsc.201300452