N,N-二甲基-2,4-二硝基-1-萘胺 | 39139-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N,N-二甲基-2,4-二硝基-1-萘胺
• 英文名称: 1-dimethylamino-2,4-dinitronaphthalene
• 英文别名: N,N-Dimethyl-2,4-dinitro-1-naphthylamin；N,N-Dimethyl-2,4-dinitronaphthalen-1-amine；N,N-dimethyl-2,4-dinitronaphthalen-1-amine
• CAS: 39139-79-2
• 化学式: C₁₂H₁₁N₃O₄
• 分子量: 261.237
• InChiKey: RHMRIRCVYOVJRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-2,4-二硝基-1-萘胺 以 水 为溶剂， 反应 25.5h， 生成 1-(Methylamino)-2,4-dinitronaphthalene
  参考文献：
  名称：

  1-二烷基氨基-2,4-二硝基萘与伯或仲胺在有机溶剂中的芳香亲核取代反应：简便的胺-胺交换

  摘要：

  1-二烷基氨基-2,4-二硝基萘的二烷基氨基（例如，二甲基，二乙基和N-正丁基-N-甲基氨基，哌啶子基和吡咯烷基）被伯胺迅速取代，尤其是在二甲基亚砜中; 但是，除了吡咯烷的情况以外，仲胺不会发生取代。

  DOI：

  10.1039/c39880000698
• 作为产物：
  描述：

  N,N-二甲基-1-萘胺 在 溶剂黄146 作用下， 生成 N,N-二甲基-2,4-二硝基-1-萘胺
  参考文献：
  名称：

  A comparative study between excess-dose users and regular-dose users of rhubarb contained in Kampo medicines

  摘要：

  With prolonged use of rhubarb-containing Kampo medicines, some patients come to ask for highdose rhubarb because of deteriorated reactivity to rhubarb. We divided patients into two groups in terms of rhubarb-dose, and compared clinical backgrounds between regular-dose group and excess-dose group. Patients who were treated with rhubarb-containing Kampo extracts (manufactured prescriptions) or Kampo formulae (decoctions) for more than 12 months were enrolled. These two groups were compared for age, sex, shape of stool, abdominal symptoms, existence of hemorrhoids, Kampo diagnosis of abdomen, past stimulant laxative use, duration of stimulant laxative use before the first administration of rhubarb, duration of rhubarb use in our hospital, and initial existence of stimulant pain caused by taking stimulant laxatives for the first time. No significant difference was shown between the two groups in terms of age, duration of stimulant laxative-use before the first prescription of rhubarb, shape of stool, abdominal symptoms, existence of hemorrhoids, or duration of rhubarb-use. However, most patients in the regular-dose group had initial stimulant pain of the abdomen upon taking stimulant laxatives for the first time, but most patients in the excess-dose group did not (p < 0.001). All patients except one in the regular dose group had the sign of "umbilical region tenderness on pressure", but half of the excess-dose group did not have it (P = 0.041). Based on these findings, the absence of "initial stimulant pain" and the absence of "umbilical region tenderness on pressure" may predict increasing or excess use of rhubarb, and long-term use of rhubarb should be discouraged more strongly in the patients without these signs.

  DOI：

  10.1078/09447110260571580

文献信息

• Aromatic Nucleophilic Substitution. XV. Stopped-flow Kinetics of the Formation and Decomposition of 1,3- and 1,1-Disubstituted Meisenheimer Complexes in the Reactions of 1-Dialkylamino-2,4-dinitronaphthalenes with Potassium Methoxide in Dimethyl Sulfoxide-Methanol
  作者：Shizen Sekiguchi、Toshio Takei、Kohji Matsui、Noboru Tone、Noboru Tomoto

  DOI：10.1246/bcsj.54.3009

  日期：1981.10

  The formation of 1,3-disubstituted anionic σ complexes, followed by 1,1-disubstituted ones was confirmed by means of absorption and NMR spectra in the reactions of 1-dialkylamino-2,4-dinitronaphthalenes with potassium methoxide in DMSO-CH3OH. The rates and activation parameters were determined by kinetic studies with use of stopped-flow and conventional spectrophotometers. The rate constants for the

  在 1-二烷基氨基-2,4-二硝基萘与甲醇钾在 DMSO-CH3OH 中的反应中，通过吸收和 NMR 光谱证实了 1,3-二取代阴离子 σ 配合物的形成，然后是 1,1-二取代。速率和活化参数通过使用停流和常规分光光度计的动力学研究确定。形成 1,3-二取代的速率常数的顺序为 1-二甲氨基->1-(N-甲基丁基)氨基->1-哌啶基->1-二乙氨基-2,4-二硝基萘，其分解具有可比性。另一方面，形成 1,1-二取代的速率常数与上述相同的顺序下降，而其分解的速率常数以 1-二甲氨基->1-(N-甲基丁基)氨基-> 1-二乙氨基->1-哌啶基-2,4-二硝基萘。从激活参数讨论了该机制。
• Aromatic Nucleophilic Substitution. VII. Electronic Structure of 1,1-Disubstituted 2,4-Dinitronaphthalene Meisenheimer Complexes
  作者：Shizen Sekiguchi、Kinzo Tsutsumi、Haruo Shizuka、Kohji Matsui、Takeshi Itagaki

  DOI：10.1246/bcsj.49.1521

  日期：1976.6

  The electronic structures of 1,1-disubstituted 2,4-dinitronaphthalene Meisenheimer complexes were studied by UV-visible and infrared spectrometry and compared with the results calculated by a semiempirical SCF-MO-CI method. The electronic transitions in the complexes were assigned to those of π-π*. Calculated transition energies and intensities agree well with the observed values. The infrared spectra

  1,1-二取代2,4-二硝基萘Meisenheimer 配合物的电子结构通过紫外-可见光和红外光谱进行了研究，并与半经验SCF-MO-CI 方法计算的结果进行了比较。配合物中的电子跃迁指定为 π-π* 的电子跃迁。计算出的跃迁能量和强度与观测值非常吻合。配合物的红外光谱表明该配合物不是电荷转移配合物或自由基阴离子，而是阴离子σ配合物。
• Ullmann; Bruck, Chemische Berichte, 1908, vol. 41, p. 3932
  作者：Ullmann、Bruck

  DOI：——

  日期：——
• Vesely; Vojtech, Collection of Czechoslovak Chemical Communications, vol. 1, p. 107,113
  作者：Vesely、Vojtech

  DOI：——

  日期：——
• Sekiguchi, Shizen; Hosokawa, Masaru; Suzuki, Tohru, Journal of the Chemical Society. Perkin transactions II, 1993, # 6, p. 1111 - 1118
  作者：Sekiguchi, Shizen、Hosokawa, Masaru、Suzuki, Tohru、Sato, Mitsuo

  DOI：——

  日期：——