N1,N1-dimethyl-5-nitronaphthalen-1-amine | 10433-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N1,N1-dimethyl-5-nitronaphthalen-1-amine
• 英文别名: 1-dimethylamino-5-nitronaphthalene；dimethyl-(5-nitro-[1]naphthyl)-amine；Dimethyl-(5-nitro-[1]naphthyl)-amin；5-Nitro-1-dimethylamino-naphthalin；Ntro-N,N-dimethylnaphtalin；1-Naphthalenamine, N,N-dimethyl-5-nitro-；N,N-dimethyl-5-nitronaphthalen-1-amine
• CAS: 10433-94-0
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: QIXOMIDTQKARSO-UHFFFAOYSA-N

物化性质

• 沸点：
  192-195 °C(Press: 14 Torr)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 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：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N1,N1-dimethyl-5-nitronaphthalen-1-amine 在 甲酸 、 palladium 10% on activated carbon 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到N1,N1-dimethylnaphthalene-1,5-diamine
  参考文献：
  名称：

  通过顺序N-甲基化调节二氨基萘的基态和激发态氧化电位

  摘要：

  合成了一系列1,5-二氨基萘衍生物，并对其进行了表征，以提供结构相似但电势变化的基态和激发态电子供体。报道了该系列的电化学和光谱性质，它们一起说明了烷基取代在芳基胺上的两个相反的结果。甲基化的诱导作用从含有单甲基氨基取代基的衍生物的基态氧化电位的降低中可以明显看出。相比之下，由于二甲基化产生的构象约束抑制了非键合电子的离域作用，因此空间效应似乎主导了含二甲基氨基取代基的衍生物基态氧化电位的增加。吸收和发射特性也响应于N-甲基化水平的提高，

  DOI：

  10.1002/cphc.200900969
• 作为产物：
  描述：

  N,N-二甲基-1-萘胺 在 硫酸 作用下， 生成 N1,N1-dimethyl-5-nitronaphthalen-1-amine
  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

• A Simple and Effective Procedure for theN-Permethylation of Amino-Substituted Naphthalenes
  作者：Vladimir I. Sorokin、Valery A. Ozeryanskii、Alexander F. Pozharskii

  DOI：10.1002/ejoc.200390085

  日期：2003.2

  ohols) with good to excellent yields. Steric hindrance does not prevent the reaction. Some amines with electron-withdrawing groups, especially at nonconjugated positions, are also alkylated. The procedure allows the combination of a reduction (catalytic or by tin dichloride in acidic media) and a methylation in a one-pot process. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  多种氨基取代的萘可以通过 Me2SO4/Na2CO3/H2O（醇）系统进行 N-全甲基化，收率非常好。空间位阻不会阻止反应。一些带有吸电子基团的胺，特别是在非共轭位置，也被烷基化。该程序允许在一锅法中将还原（催化或通过酸性介质中的二氯化锡）和甲基化相结合。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Kurasov, L. A.; Pozharskii, A. F.; Kuz'menko, V. V., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, p. 520 - 525
  作者：Kurasov, L. A.、Pozharskii, A. F.、Kuz'menko, V. V.、Klyuev, N. A.、Chernyshev, A. I.、et al.

  DOI：——

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

  DOI：——

  日期：——
• KURASOV, L. A.;POZHARSKIJ, A. F.;KUZMENKO, V. V.;KLYUEV, N. A.;CHERNYSHEV+, ZH. ORGAN. XIMII, 1983, 19, N 3, 590-597
  作者：KURASOV, L. A.、POZHARSKIJ, A. F.、KUZMENKO, V. V.、KLYUEV, N. A.、CHERNYSHEV+

  DOI：——

  日期：——
• A comparative study between excess-dose users and regular-dose users of rhubarb contained in Kampo medicines
  作者：N. Mantani、T. Kogure、S. Sakai、M. Kainuma、Y. Kasahara、A. Niizawa、Y. Shimada、K. Terasawa

  DOI：10.1078/09447110260571580

  日期：2002.1

  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.