2-异氰基-1-甲氧基-4-硝基苯 | 1983-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-异氰基-1-甲氧基-4-硝基苯
• 英文名称: 2-methoxy-5-nitrobenzeneisonitrile
• 英文别名: 2-methoxy-5-nitrophenylisocyanide；2-Isocyano-1-methoxy-4-nitrobenzene
• CAS: 1983-95-5
• 化学式: C₈H₆N₂O₃
• mdl: MFCD01937389
• 分子量: 178.147
• InChiKey: ZJZZTWHYNNWBJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-异氰基-1-甲氧基-4-硝基苯 、 水杨醛 在 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以20%的产率得到2-{[(E)-2-(2-Methoxy-5-nitro-phenylamino)-benzofuran-3-ylimino]-methyl}-phenol
  参考文献：
  名称：

  Studies on Isocyanides and Related Compounds. Synthesis of Benzofuran Derivatives

  摘要：

  在Ugi四组分缩合反应条件下，2-羟基苯甲醛(1a)、异氰化物2和甲酸铵之间的反应，形成了2-烷基氨基和2-芳基氨基-3-[(2-羟基苯亚甲基)氨基]苯并呋喃3a-c。类似地，使用5-溴-2-羟基苯甲醛(1b)作为羰基化合物，则得到2-烷基氨基和2-芳基氨基-5-溴-3-[(5-溴-2-羟基苯亚甲基)氨基]苯并呋喃3d-f。

  DOI：

  10.1055/s-1991-26628
• 作为产物：
  描述：

  2-氟-5-硝基苯胺 在 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 反应 18.0h， 生成 2-异氰基-1-甲氧基-4-硝基苯
  参考文献：
  名称：

  N取代的苯并咪唑的简便合成

  摘要：

  摘要 开发了N-取代的苯并咪唑衍生物的特别温和且有效的一锅合成。2-氟-5-硝基苯基异氰酸酯与多种伯胺反应，以中等至非常高的收率（35–95％； 20个实例）提供相应的产品。 开发了N-取代的苯并咪唑衍生物的特别温和且有效的一锅合成。2-氟-5-硝基苯基异氰酸酯与多种伯胺反应，以中等至非常高的收率（35–95％； 20个实例）提供相应的产品。

  DOI：

  10.1055/s-0035-1562436

文献信息

• FR1384209
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel Hexakis(areneisonitrile)technetium(I) Complexes as Radioligands Targeted to the Multidrug Resistance P-Glycoprotein
  作者：Lee W. Herman、Vijay Sharma、James F. Kronauge、Eva Barbarics、Lisa A. Herman、David Piwnica-Worms

  DOI：10.1021/jm00015a018

  日期：1995.7

  Transport substrates and modulators of the human multidrug resistance (MDR1) P-glycoprotein (Pgp) are generally lipophilic cationic compounds, many with substituted aryl moieties, We sought to synthesize aromatic technetium-isonitrile complexes to enable functional detection in vivo of Pgp expression in tissues. A series of substituted aromatic isonitrile analogs were synthesized from their corresponding amines by reaction with dichlorocarbene under phase transfer-catalyzed conditions, and the non-carrier-aaded hexakis(areneisonitrile)Tc-99m(I) complexes were produced by reaction with pertechnetate in the presence of sodium dithionite. Cellular accumulation in. vitro, whole body biodistribution, and the imaging properties of these lipophilic, monocationic organometallic complexes were determined in Chinese hamster lung fibroblasts expressing MDR Pgp, in normal rats, and in rabbits, respectively. For this initial series, verapamil (50 mu M), the classical Pgp modulator, significantly enhanced cellular accumulation or displaced binding of Tc complexes of 1b, 1d, 1h, 2a, 2d, 3a, and 3b, indicative of targeted interactions with Pgp. Most complexes, despite their modestly high lipophilicity, were excluded by the blood/brain barrier, and several complexes displayed simultaneously high hepatobiliary and renal excretion in vivo, consistent with the physiological expression pattern of Pgp in these tissues. Selected Tc- and Re-areneisonitrile complexes of this class have potential applicability to the functional imaging and modulation, respectively, of MDR Pgp in human tissues.
• Studies on Isocyanides and Related Compounds. Synthesis of Benzofuran Derivatives
  作者：Ricardo Bossio、Stefano Marcaccini、Paola Paoli、Roberto Pepino、Cecilia Polo

  DOI：10.1055/s-1991-26628

  日期：——

  The reaction between 2-hydroxybenzaldehyde (1a), isocyanides 2, and ammonium formate, in the conditions of the Ugi four-component condensation, affords 2-alkylamino- and 2-arylamino-3-[(2-hydroxybenzylidene)amino]benzofurans 3a-c. Analogously by employing 5-bromo-2-hydroxybenzaldehyde (1b) as the carbonyl compound, 2-alkylamino- and 2-arylamino-5-bromo-3- [(5-bromo-2-hydroxybenzylidene)amino]benzofurans 3d-f are obtained.

  在Ugi四组分缩合反应条件下，2-羟基苯甲醛(1a)、异氰化物2和甲酸铵之间的反应，形成了2-烷基氨基和2-芳基氨基-3-[(2-羟基苯亚甲基)氨基]苯并呋喃3a-c。类似地，使用5-溴-2-羟基苯甲醛(1b)作为羰基化合物，则得到2-烷基氨基和2-芳基氨基-5-溴-3-[(5-溴-2-羟基苯亚甲基)氨基]苯并呋喃3d-f。
• Facile Synthesis of N-Substituted Benzimidazoles
  作者：Santosh Kurhade、Arianna Rossetti、Alexander Dömling

  DOI：10.1055/s-0035-1562436

  日期：——

  A particularly mild and efficient one-pot synthesis of N-substituted benzimidazole derivatives was developed. 2-Fluoro-5-nitrophenylisocyanide reacts with a diverse set of primary amines to afford the respective products in moderate to very good yield (35–95%; 20 examples). A particularly mild and efficient one-pot synthesis of N-substituted benzimidazole derivatives was developed. 2-Fluoro-5-nitrophenylisocyanide

  摘要 开发了N-取代的苯并咪唑衍生物的特别温和且有效的一锅合成。2-氟-5-硝基苯基异氰酸酯与多种伯胺反应，以中等至非常高的收率（35–95％； 20个实例）提供相应的产品。 开发了N-取代的苯并咪唑衍生物的特别温和且有效的一锅合成。2-氟-5-硝基苯基异氰酸酯与多种伯胺反应，以中等至非常高的收率（35–95％； 20个实例）提供相应的产品。