4-(2,4-二硝基萘-1-基)吗啉 | 113748-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-(2,4-二硝基萘-1-基)吗啉
• 英文名称: 1-morpholino-2,4-dinitronaphthalene
• 英文别名: 4-(2,4-Dinitronaphthalen-1-yl)morpholine
• CAS: 113748-36-0
• 化学式: C₁₄H₁₃N₃O₅
• 分子量: 303.274
• InChiKey: XEBFGXIHNRNKKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吗啉 、 phenyl 2,4-dinitronaphthyl ether 以 二甲基亚砜 为溶剂， 生成 4-(2,4-二硝基萘-1-基)吗啉
  参考文献：
  名称：

  Kinetic and equilibrium studies of ?-adduct formation and nucleophilic substitution in the reactions of morpholine with 1,3,5-trinitrobenzene and some phenyl aryl ethers in dimethyl sulphoxide

  摘要：

  Reactions of morpholine in dimethyl sulphoxide at unsubstituted ring positions of 1,3,5-trinitrobenzene, and phenyl 2,4,6-trinitrophenyl ether, yield anionic sigma-adducts via zwitterionic intermediates. Reactions at the 1-position of phenyl 2,4,6-trinitrophenyl ether, phenyl 2,4-dinitronaphthyl ether, and phenyl 2,4-dinitrophenyl ether result in substitution of the phenoxy groups. In both these reaction types proton-transfer is rate-limiting. Comparison of kinetic and equilibrium data with those for corresponding reactions of piperidine shows that rate constants for proton transfer are similar for the two amines, but equilibrium constants for zwitterion formation have lower values for morpholine, the less basic amine. Implications for base catalysis are discussed.

  DOI：

  10.1002/(sici)1099-1395(199603)9:3<152::aid-poc769>3.0.co;2-4

文献信息

• Kinetic and equilibrium studies of ?-adduct formation and nucleophilic substitution in the reactions of morpholine with 1,3,5-trinitrobenzene and some phenyl aryl ethers in dimethyl sulphoxide
  作者：Rachel A. Chamberlin、Michael R. Crampton、Ian A. Robotham

  DOI：10.1002/(sici)1099-1395(199603)9:3<152::aid-poc769>3.0.co;2-4

  日期：1996.3

  Reactions of morpholine in dimethyl sulphoxide at unsubstituted ring positions of 1,3,5-trinitrobenzene, and phenyl 2,4,6-trinitrophenyl ether, yield anionic sigma-adducts via zwitterionic intermediates. Reactions at the 1-position of phenyl 2,4,6-trinitrophenyl ether, phenyl 2,4-dinitronaphthyl ether, and phenyl 2,4-dinitrophenyl ether result in substitution of the phenoxy groups. In both these reaction types proton-transfer is rate-limiting. Comparison of kinetic and equilibrium data with those for corresponding reactions of piperidine shows that rate constants for proton transfer are similar for the two amines, but equilibrium constants for zwitterion formation have lower values for morpholine, the less basic amine. Implications for base catalysis are discussed.