N,N'-Di-p-tolyl-naphthalene-1-carboxamidine | 60566-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-Di-p-tolyl-naphthalene-1-carboxamidine
• 英文别名: N,N'-bis(4-methylphenyl)naphthalene-1-carboximidamide
• CAS: 60566-19-0
• 化学式: C₂₅H₂₂N₂
• 分子量: 350.463
• InChiKey: LCKGQJOEHXQJOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N'-Di-p-tolyl-naphthalene-1-carboxamidine 在 sodium hydroxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 49.0h， 生成
  参考文献：
  名称：

  摘要：

  A procedure has been developed for the synthesis of N-cyclopentadienyl amidinium ylides of the general formula C-5(CO2Me)(4)[ArNC(Ar)NHAr]. According to the X-ray diffraction data, H-1 and C-13 NMR spectroscopy, and MNDO quantum-chemical calculations, the title compounds have a zwitterionic structure with the positive charge localized over the amidine N-C-N triad, and the negative charge, over the cyclopentadiene fragment. The configuration of the amidine moiety is stabilized by additional interaction of the NH hydrogen atom with the negatively charged cyclopentadiene ring (pi-bonding). The ylides are chiral due to atropoisomerism arising from a high energy barrier (DeltaG(298)(not equal) > 25 kcal/mol) to rotation of the Ar' substituent about the ordinary C-C bond in the amidinium fragment.

  DOI：

  10.1023/a:1020897411534

文献信息

• Novel degenerate sigmatropic rearrangements of amidines
  作者：Vladimir I. Minkin、Igor E. Mikhailov、Galina A. Dushenko

  DOI：10.1039/c39880001181

  日期：——

  yclopentadienyl)-N,N′-diarylamidines (2) prepared by the reaction of N,N′-diarylamidines with 5-nitro-1,2,3,4,5-pentakismethoxycarbonylcyclopentadiene show fluxional behaviour arising from degenerate sigmatropic 1,3-shifts of the nitroso group in (1) and 3,3-shifts of the amidinyl moiety in (2).

  Ñ -Nitroso- Ñ，Ñ '-diarylamidines（1）和ñ - （1,2,3,4,5- pentakismethoxycarbonylcyclopentadienyl） - ñ，Ñ '-diarylamidines（2通过反应制得）Ñ，Ñ '-diarylamidines具有5-硝基1,2,3,4,5-戊基甲氧基羰基环戊二烯的化合物显示出由（1）中亚硝基的简并的1,3-移位和（2）中the基部分的3,3-移位引起的通量行为。
• Mikhailov; Dushenko; Zhunke, Russian Journal of Organic Chemistry, 1998, vol. 34, # 8, p. 1127 - 1130
  作者：Mikhailov、Dushenko、Zhunke、Miigge、Minkin

  DOI：——

  日期：——
• ——
  作者：G. A. Dushenko、I. E. Mikhailov、G. Reck、B. Schulz、A. Zschunke、N. N. Kharabaev、V. I. Minkin

  DOI：10.1023/a:1020897411534

  日期：——

  A procedure has been developed for the synthesis of N-cyclopentadienyl amidinium ylides of the general formula C-5(CO2Me)(4)[ArNC(Ar)NHAr]. According to the X-ray diffraction data, H-1 and C-13 NMR spectroscopy, and MNDO quantum-chemical calculations, the title compounds have a zwitterionic structure with the positive charge localized over the amidine N-C-N triad, and the negative charge, over the cyclopentadiene fragment. The configuration of the amidine moiety is stabilized by additional interaction of the NH hydrogen atom with the negatively charged cyclopentadiene ring (pi-bonding). The ylides are chiral due to atropoisomerism arising from a high energy barrier (DeltaG(298)(not equal) > 25 kcal/mol) to rotation of the Ar' substituent about the ordinary C-C bond in the amidinium fragment.