N-(methoxycarbonyl)oxy-4-nitrobenzamidine | 224963-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(methoxycarbonyl)oxy-4-nitrobenzamidine
• 英文别名: [(E)-[amino-(4-nitrophenyl)methylidene]amino] methyl carbonate
• CAS: 224963-67-1
• 化学式: C₉H₉N₃O₅
• 分子量: 239.188
• InChiKey: ILHCPTMQSWBEIH-UHFFFAOYSA-N

物化性质

• 沸点：
  333.5±44.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(methoxycarbonyl)oxy-4-nitrobenzamidine 在 吡啶 作用下， 反应 7.0h， 生成 3-(4-nitrophenyl)-1,2,4-oxadiazol-5(4H)-one
  参考文献：
  名称：

  EP1612204

  摘要：

  公开号：
• 作为产物：
  描述：

  N'-hydroxy-4-nitrobenzimidamide 、 氯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以17%的产率得到N-(methoxycarbonyl)oxy-4-nitrobenzamidine
  参考文献：
  名称：

  Kinetics of Methanolysis of Substituted Benzamide O-(Phenoxycarbonyl)- and O-(Alkoxycarbonyl)oximes Catalyzed by Sodium Methanolate

  摘要：

  对苯甲酰胺取代物的甲醇解反应动力学，如在25°C下由甲醇酸钠催化的O-(苯氧羰基)-和O-(烷氧羰基)肟进行了研究。该反应分为两步。在第一步中，取代苯氧基被交换成甲氧基，形成取代的O-(甲氧羰基)肟，这是一个较快的步骤。在第二步中，苯甲酰胺肟被消除，生成二甲基碳酸酯。在两个步骤中，速率常数与甲醇酸钠浓度的关系图的斜率均呈增加趋势。在18-冠-6的存在下，图形是线性的，速率常数比没有冠醚存在时更低。假设钠阳离子催化的反应构成了与MeONa离子对反应的反应速率决定步骤，确定了底物与甲醇酸钠离子对反应的速率常数。对于芳氧基和取代苯甲酰胺肟的消除，与离子对反应的速率常数分别比非催化反应高大约12倍和20倍。对于取代酚的pKa的对数值(βlg)的依赖关系的斜率，未催化消除取代苯氧基反应的值为-0.52，消除苯甲酰胺肟基团的值为-0.83，与离子对反应的值为-0.53。在第一步和可能也在第二步中，反应通过协同机制进行。对于取代苯甲酰胺O-(4-硝基苯氧羰基)肟的甲醇解反应的相对较高的ρ值，0.63，表明过渡态的结构接近四面体中间体的结构。

  DOI：

  10.1135/cccc19990265

文献信息

• Hydrazone derivative
  申请人：Kawagoe Keiichi

  公开号：US20060276433A1

  公开（公告）日：2006-12-07

  A compound represented by the following formula (I): wherein R 1 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R 2 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R 3 represents hydrogen, etc.; Ar represents a divalent group derived from aromatic hydrocarbon, etc.; X represents a single bond, linear or branched alkylene having from 1 to 3 carbon atoms which may have a substituent, etc.; and G represents halogen, a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc., a salt thereof or a solvate thereof; and an agent for inhibiting aggregation and/or deposition of an amyloid protein or an amyloid-like protein, which comprises the compound, a salt thereof or a solvate thereof.

  以下是式子（I）所代表的化合物： 其中，R1代表氢、芳基（可能带有取代基）、饱和或不饱和的5-至7-成员杂环基（可能带有取代基）等； R2代表氢、芳基（可能带有取代基）、饱和或不饱和的5-至7-成员杂环基（可能带有取代基）等； R3代表氢等； Ar代表从芳香族碳氢化合物衍生的二价基团等； X代表单键、线性或支链烷基，具有1至3个碳原子，可能带有取代基等； G代表卤素、饱和或不饱和的5-或6-成员环烃基（可能带有取代基）、饱和或不饱和的5-至7-成员杂环基（可能带有取代基）等，其盐或溶剂化物；以及用于抑制淀粉样蛋白或类淀粉样蛋白的聚集和/或沉积的药剂，包括该化合物、其盐或溶剂化物。
• HYDRAZONE DERIVATIVE
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1612204A1

  公开（公告）日：2006-01-04

  A compound represented by the following formula (I): wherein R1 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R2 represents hydrogen, aryl which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc.; R3 represents hydrogen, etc.; Ar represents a divalent group derived from aromatic hydrocarbon, etc.; X represents a single bond, linear or branched alkylene having from 1 to 3 carbon atoms which may have a substituent, etc.; and G represents halogen, a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group which may have a substituent, a saturated or unsaturated 5- to 7-membered heterocyclic group which may have a substituent, etc., a salt thereof or a solvate thereof; and an agent for inhibiting aggregation and/or deposition of an amyloid protein or an amyloid-like protein, which comprises the compound, a salt thereof or a solvate thereof

  下式(I)所代表的化合物： 其中 R1 代表氢、可能具有取代基的芳基、可能具有取代基的饱和或不饱和 5 至 7 元杂环基团等；R2 代表氢、可能具有取代基的芳基、可能具有取代基的饱和或不饱和 5 至 7 元杂环基团等；R3 代表氢等。Ar 代表衍生自芳香烃的二价基团等；X 代表具有 1 至 3 个碳原子的单键、线性或支链亚烷基（可具有取代基）等；G 代表卤素、饱和或不饱和的 5 或 6 元环状烃基（可具有取代基）、饱和或不饱和的 5 至 7 元杂环基（可具有取代基）等、一种抑制淀粉样蛋白或类淀粉样蛋白聚集和/或沉积的制剂，其中包括该化合物、其盐或其溶液。
• EP1612204
  申请人：——

  公开号：——

  公开（公告）日：——
• Kinetics of Methanolysis of Substituted Benzamide O-(Phenoxycarbonyl)- and O-(Alkoxycarbonyl)oximes Catalyzed by Sodium Methanolate
  作者：Libor Dušek、Jaromír Kaválek、Vojeslav Štěrba

  DOI：10.1135/cccc19990265

  日期：——

  The kinetics of methanolysis of substituted benzamide O-(phenoxycarbonyl)- and O-(alkoxycarbonyl)oximes catalyzed by sodium methanolate was studied at 25 °C. The reaction proceeds in two steps. In the first, faster step, the substituted phenoxy group is exchanged for a methoxy group giving rise to substituted O-(methoxycarbonyl)oximes. In the second step, a benzamide oxime is eliminated and dimethyl carbonate is formed. The slope of the plot of the rate constant in dependence on the sodium methanolate concentration has an increasing tendency in both steps. In the presence of 18-crown-6, the plots are linear and the rate constants are lower than in the absence of the crown ether. The rate constants of the reaction of the substrate with the methanolate ion and with the MeONa ion pair were determined assuming that the sodium cation-catalyzed reactions constitute the rate-determining step of the reaction of the substrate with the MeONa ion pair. For the elimination of the aryloxy group and of the substituted benzamide oxime, the rate constants of the reaction with the ion pair are roughly twelvefold and twentyfold higher, respectively, than in the uncatalyzed reaction. The slope of the dependence of log k on the pK_a of the substituted phenols (β_lg) has the value of -0.52 for the uncatalyzed reaction of elimination of the substituted phenoxy group, -0.83 for the elimination of the benzamide oxime group, and -0.53 for the reaction with the ion pair. In the first step and probably also in the second step, the reaction proceeds by the concerted mechanism. The relatively high ρ value of methanolysis of substituted benzamide O-(4-nitrophenoxycarbonyl)oximes, 0.63, suggests that the structure of the transition state approaches that of the tetrahedral intermediate.

  对苯甲酰胺取代物的甲醇解反应动力学，如在25°C下由甲醇酸钠催化的O-(苯氧羰基)-和O-(烷氧羰基)肟进行了研究。该反应分为两步。在第一步中，取代苯氧基被交换成甲氧基，形成取代的O-(甲氧羰基)肟，这是一个较快的步骤。在第二步中，苯甲酰胺肟被消除，生成二甲基碳酸酯。在两个步骤中，速率常数与甲醇酸钠浓度的关系图的斜率均呈增加趋势。在18-冠-6的存在下，图形是线性的，速率常数比没有冠醚存在时更低。假设钠阳离子催化的反应构成了与MeONa离子对反应的反应速率决定步骤，确定了底物与甲醇酸钠离子对反应的速率常数。对于芳氧基和取代苯甲酰胺肟的消除，与离子对反应的速率常数分别比非催化反应高大约12倍和20倍。对于取代酚的pKa的对数值(βlg)的依赖关系的斜率，未催化消除取代苯氧基反应的值为-0.52，消除苯甲酰胺肟基团的值为-0.83，与离子对反应的值为-0.53。在第一步和可能也在第二步中，反应通过协同机制进行。对于取代苯甲酰胺O-(4-硝基苯氧羰基)肟的甲醇解反应的相对较高的ρ值，0.63，表明过渡态的结构接近四面体中间体的结构。