ethyl 1H-perimidine-2-carboxylate | 109735-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 1H-perimidine-2-carboxylate
• 英文别名: ethyl perimidine-2-carboxylate；1H-perimidine-2-carboxylic acid ethyl ester；1H-Perimidin-2-carbonsaeure-aethylester；perimidine-2-carboxylic acid ethyl ester；1H-Perimidine-2-carboxylic acid, ethyl ester
• CAS: 109735-80-0
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: WQQGSRMAMYBPRM-UHFFFAOYSA-N

物化性质

• 熔点：
  199-201 °C(Solv: xylene (1330-20-7))
• 沸点：
  422.2±28.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1H-perimidine-2-carboxylate 在 溶剂黄146 、 锌 作用下， 生成 2-hydroxymethyl perimidine
  参考文献：
  名称：

  Sachs, Justus Liebigs Annalen der Chemie, 1909, vol. 365, p. 162

  摘要：

  DOI：
• 作为产物：
  描述：

  1,8-二硝基萘 在 iodophosphorus 、 水 作用下， 生成 ethyl 1H-perimidine-2-carboxylate
  参考文献：
  名称：

  Meyer,R.; Mueller, Chemische Berichte, 1897, vol. 30, p. 772

  摘要：

  DOI：

文献信息

• 2-Substituted-1H-perimidines: Synthesis, crystal structure and DFT calculations
  作者：Irena Sović、Gordana Pavlović、Anastasios G. Papadopoulos、Dubravka Šišak、Grace Karminski-Zamola

  DOI：10.1016/j.molstruc.2013.03.020

  日期：2013.6

  ne 5 . The compounds are characterized by MS, IR spectroscopy, single-crystal X-ray diffraction (SCXRD) ( 2 ), and powder X-ray diffraction (PXRD) ( 5 ), as well as DFT calculations ( 3 , 4 and 5 ) and by the NMR spectroscopy in the solution ( 2 – 5 ). Single-crystal X-ray diffraction proved that the compound 2 exists in the solid state as imine tautomer. The molecular structure that compound 5 adopt

  摘要 Perimidines 或1 H - perimidines 代表一类重要的杂环化合物，由二氢嘧啶环周围稠合到萘部分构成。由于在一个或另一个环内氮原子或两者上的两个可能的氢位置，它们表现出 1,3-环互变异构现象，分别导致亚胺或烯胺形式。2-取代的-1 H-perimidine 的亚胺形式可以表现出关于双 CN 键的 2-取代基的顺式或反式取向。在这里，我们报告了四种 2-取代的 perimidine 衍生物的合成：2-羟甲基-perimidine 2、ethyl-1 H-perimidine-2-carboxylate 3、perimidine-2-羧酸 4 和 2-cyanomethyl-perimidine 5。通过质谱、红外光谱、单晶 X 射线衍射 (SCXRD) ( 2 ) 和粉末 X 射线衍射 (PXRD) ( 5 ) 对化合物进行表征，以及 DFT 计算（3、4 和 5）和溶液中的
• Vinylphosphonium salt mediated simple synthesis of 7-oxo-7H-pyrido[1,2,3-cd]perimidine derivatives. Dynamic NMR spectroscopic study of prototropic tautomerism in ethyl 1H-perimidine-2-carboxylate
  作者：Issa Yavari、Mehdi Adib、Fatemeh Jahani-Moghaddam、Hamid R Bijanzadeh

  DOI：10.1016/s0040-4020(02)00759-7

  日期：2002.8

  chloroform, while the later compound remained unchanged under the same reaction conditions. The free-energy barrier (ΔG≠) for prototropic tautomerism in ethyl 1H-perimidine-2-carboxylate is determined by dynamic 1H NMR studies to be 50.6 kJ mol−1. The methylene protons of 5-ethyl 9-methyl 7-oxo-7H-pyrido[1,2,3-cd]perimidine-5,9-dicarboxylate are diastereotopic as a result of peri interaction of carboethoxy

  在乙炔基二羧酸二甲酯与三苯基膦之间的反应中生成的1：1反应性中间体被1 H -perimidine-2-羧酸乙酯截留，生成5-乙基9-甲基7-氧代-7 H-吡啶基[1,2,3- cd ] perimidine-5,9-dicarboxylate and 5-ethyl 9-methyl 1- [3-methoxy-1-（methoxymethoxy））-3-oxo-1-propenyl] -7-oxo-7 H -pyrido [1,2 ，3- CD ]啶-5,9-二羧酸二甲酯在近7：1分的比例和总体良好的产率。这些化合物中的第一个被定量转化为10-[（2-乙氧基-2-氧乙酰基）氨基] -2-羟基苯并[ h ]乙基通过在水饱和的氯仿中回流，使]喹啉-4-羧酸盐，而后一化合物在相同反应条件下保持不变。通过动态1 H NMR研究确定1 H -perimidine-2-羧酸乙酯中质子互变异构的自由能垒（ΔG
• Potential antitumor agents. 53. Synthesis, DNA binding properties, and biological activity of perimidines designed as minimal DNA-intercalating agents
  作者：John M. Herbert、Paul D. Woodgate、William A. Denny

  DOI：10.1021/jm00394a025

  日期：1987.11

  A series of compounds based on perimidine have been synthesized and evaluated for their DNA-binding properties and antitumor activity. The fused tricyclic permidine chromophore appears to be the minimal structural requirement for intercalative binding to DNA since the mode of binding could be dictated by the position of attachment of the side chain. The intercalating compounds have DNA association constants (log K = 5.8-6.5) and cytotoxic potencies (IC50 = 500-1500 nM) comparable to those shown by other classes of linear, tricyclic DNA-intercalating antitumor agents (acridinecarboxamides, phenazinecarboxamides), but none of the compounds showed in vivo activity.
• Transformation of Furan-2,3-diones with 1,8-Diaminonaphthalene to Naphtho-[1,8-<i>ef</i>][1,4]diazepin-2(1<i>H</i>)-ones
  作者：Şevket Hakan Üngören

  DOI：10.1080/00397910902796094

  日期：2009.9.18

  Naphtho[1,8-ef][1,4]diazepin-2(1H)-ones were obtained from furan-2,3-diones with 1,8-diaminonaphthalene.
• de Aguiar, Chemische Berichte, 1874, vol. 7, p. 309
  作者：de Aguiar

  DOI：——

  日期：——