(1S,9R)-4-(2-methylphenyl)-8-oxa-4,5-diaza-2-azoniatetracyclo[7.7.0.02,6.011,16]hexadeca-2,5,11,13,15-pentaene;chloride | 1360651-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,9R)-4-(2-methylphenyl)-8-oxa-4,5-diaza-2-azoniatetracyclo[7.7.0.02,6.011,16]hexadeca-2,5,11,13,15-pentaene;chloride
• CAS: 1360651-94-0
• 化学式: C₁₉H₁₈N₃O*Cl
• 分子量: 339.824
• InChiKey: VWVUBCSXJNDZOD-ZFNKBKEPSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4AS,9AR)-4,4A,9,9A-四氢茚并[2,1-B][1,4]噁嗪-3(2H)-酮 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯苯 为溶剂， 反应 26.5h， 生成 (1S,9R)-4-(2-methylphenyl)-8-oxa-4,5-diaza-2-azoniatetracyclo[7.7.0.02,6.011,16]hexadeca-2,5,11,13,15-pentaene;chloride
  参考文献：
  名称：

  Oxyanion Steering and CH−π Interactions as Key Elements in an N-Heterocyclic Carbene-Catalyzed [4 + 2] Cycloaddition

  摘要：

  The N-heterocyclic carbene catalyzed [4 + 2] cycloaddition has been shown to give gamma,delta-unsaturated delta-lactones in excellent enantio- and diastereoselectivity. However, preliminary computational studies of the geometry of the intermediate enolate rendered ambiguous both the origins of selectivity and the reaction pathway. Here, we show that a concerted, but highly asynchronous, Diels-Alder reaction occurs rather than the stepwise Michael-type or Claisen-type pathways. In addition, two crucial interactions are identified that enable high selectivity an oxyanion-steering mechanism and a CH-pi interaction. The calculations accurately predict the enantioselectivity of a number of N-heterocyclic carbene catalysts in the hetero-Diels-Alder reaction.

  DOI：

  10.1021/ja302761d