6-Pyridin-4-yl-2-pyridin-3-yl-3,6-dihydro-2H-[1,2]oxazine | 216018-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-Pyridin-4-yl-2-pyridin-3-yl-3,6-dihydro-2H-[1,2]oxazine
• 英文别名: 2-Pyridin-3-yl-6-pyridin-4-yl-3,6-dihydrooxazine
• CAS: 216018-76-7
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: QPIWKZPGTFURRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-nitrosopyridine 、 4-pyridyl butadiene 以 氘代氯仿 为溶剂， 生成 6-Pyridin-4-yl-2-pyridin-3-yl-3,6-dihydro-2H-[1,2]oxazine
  参考文献：
  名称：

  Acceleration of a hetero-Diels–Alder reaction by cyclic metalloporphyrin trimers

  摘要：

  吡啶基丁二烯和3-亚硝基吡啶之间的杂二烯-阿尔德反应可通过多种金属卟啉三聚体加速；速率加速与产物结合强度之间存在弱相关性。

  DOI：

  10.1039/a806070c

文献信息

• Acceleration of a hetero-Diels–Alder reaction by cyclic metalloporphyrin trimers
  作者：Maurus Marty、Zöe Clyde-Watson、Lance J. Twyman、Moshe Nakash、Jeremy K. M. Sanders

  DOI：10.1039/a806070c

  日期：——

  The hetero-Diels–Alder reaction between a pyridylbutadiene and 3-nitrosopyridine is accelerated by a variety of metalloporphyrin trimers; there is a weak correlation between rate acceleration and product binding strength.

  吡啶基丁二烯和3-亚硝基吡啶之间的杂二烯-阿尔德反应可通过多种金属卟啉三聚体加速；速率加速与产物结合强度之间存在弱相关性。
• Product-Induced Distortion of a Metalloporphyrin Host:  Implications for Acceleration of Diels−Alder Reactions
  作者：Moshe Nakash、Zöe Clyde-Watson、Neil Feeder、John E. Davies、Simon J. Teat、Jeremy K. M. Sanders

  DOI：10.1021/ja9922227

  日期：2000.6.1

  New cyclic metalloporphyrin hosts, 6 and 7, have been prepared. At 0.33 mM in dichloromethane at 25 degrees C, they accelerate 65-fold and 840-fold respectively the reaction of diene 1 and dienophile 2 and also bind the hetero Diels-Alder product 3 very strongly. More importantly, small single crystals of solvated 6, 7, and the 6 3 complex were grown and their structures were determined. As the Diels-Alder product resembles the Diels-Alder transition state, the structures of the product-free host 6 and the 6 3 host-product complex allow, for the first time for synthetic receptors, a detailed structural analysis of the geometrical changes imposed on an accelerating agent on binding of a Diels-Alder product. Comparison of these structures reveals that when the Diels-Alder product 3 is bound within the cavity, it induces significant structural changes in 6. This provides the first crystallographic structural evidence that accelerated product formation can be accompanied by substantial host distortion. Desolvation of host and guests emerges as another factor, implying that solvent stabilization is not as significant for the host-accelerated reaction as in the control (host free) reaction.