2-isopropyl-4-nitrotoluene | 103096-00-0

• 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: 2-isopropyl-4-nitrotoluene
• 英文别名: 4-Nitro-o-cymene；2-isopropyl-1-methyl-4-nitro-benzene；2-Isopropyl-1-methyl-4-nitro-benzol；4-Nitro-2-isopropyl-toluol；1-Methyl-4-nitro-2-propan-2-ylbenzene
• CAS: 103096-00-0
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: OLYVGLJEMPYXOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  144-145 °C(Press: 15 Torr)
• 密度：
  1.078 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻-异丙基苯 在 nitronium tetrafluoborate 作用下， 以 环丁砜 为溶剂， 生成 2-isopropyl-4-nitrotoluene
  参考文献：
  名称：

  Aromatic Substitution. XX. Intact and Dealkylating Nitration of Propylated and Butylated Alkylbenzenes with Nitronium Tetronium Tetrafluoroborate

  摘要：

  DOI：

  10.1021/ja01060a020

文献信息

• Electrophilic aromatic substitution. Part 24. The nitration of isopropylbenzene, 2- and 4-isopropyltoluene, 1-chloro-4-isopropylbenzene, 4-isopropylanisole, and 2-bromotoluene: nitrodeisopropylation
  作者：Ajay K. Manglik、Roy B. Moodie、Kenneth Schofield、Geoffrey D. Tobin、Robert G. Coombes、Panicos Hadjigeorgiou

  DOI：10.1039/p29800001606

  日期：——

  The kinetics and products of nitration in aqueous sulphuric acid of the title compounds have been studied. 4-Isopropyl-phenol and -anisole are nitrated at or near the encounter rate. In 65–79% H2SO4 2-isopropyltoluene suffers ca. 25%ipso-attack; the only fate of WiPri(ipso-Wheland intermediate) is nitrodeisopropylation. From 4-isopropyltoluene WiPri is also nitrodeisopropylated, but some 1,2-nitro-migration

  研究了标题化合物在硫酸水溶液中硝化的动力学和产物。将4-异丙基苯酚和-茴香醚以相遇率或相近的速率进行硝化。在65-79％的H 2 SO 4 2- isopropyltoluene患有约 25％ipso-攻击；W的唯一命运我镨我（本位-Wheland中间体）是nitrodeisopropylation。从4-异丙基甲苯W i Pr i也被硝基异异丙基化，但是可能发生一些1，2-硝基迁移。来自同一化合物W i Me可能被水捕获，重排或产生4-甲基苯乙酮; 提出了形成最后化合物的机制。硝基去异丙基化在没有水的帮助下发生。对于4-异丙基茴香醚，脱去甲氧基化和硝基去异丙基化是W i Pr i形成的结果。该结果与通过增加两个酸度而增加酸度对C-4的攻击，在没有水的帮助下失去异丙基，以及未观察到的中间体4-异丙基-4-硝基环己-2,5-二烯酮的分解相一致。一种酸催化的方法得到4-硝基苯酚和可能的4-异丙
• Metal-Catalyzed Carbon-Fluorine Bond Formation
  申请人：Buchwald Stephen L.

  公开号：US20110015401A1

  公开（公告）日：2011-01-20

  One aspect of the invention relates to a metal-catalyzed conversion of aryl halides and sulfonates to the corresponding aryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of heteroaryl halides and sulfonates to the corresponding heteroaryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of vinyl halides and sulfonates to the corresponding vinyl fluorides. In certain embodiments, simple fluoride sources, such as AgF and CsF, are used. In certain embodiments, the transformations tolerate a wide range of functional groups, allowing for introduction of fluorine atoms into highly functionalized organic molecules.

  该发明的一个方面涉及将芳基卤化物和磺酸酯金属催化转化为相应的芳基氟化物。该发明的另一个方面涉及将杂环芳基卤化物和磺酸酯金属催化转化为相应的杂环芳基氟化物。该发明的另一个方面涉及将乙烯卤化物和磺酸酯金属催化转化为相应的乙烯氟化物。在某些实施例中，使用简单的氟化物源，如AgF和CsF。在某些实施例中，这些转化可以容忍各种官能团，从而使高度官能化的有机分子中引入氟原子成为可能。
• “Ipso” Aromatic Nitration in the Gas Phase
  作者：M. Attinà、F. Cacace、A. Ricci

  DOI：10.1021/jp951563d

  日期：1996.1.1

  radiolytic technique. The results provide the first demonstration of gas-phase electrophilic aromatic nitrodealkylation and a quantitative evaluation of its efficiency relative to the competing nitration process. Dealkylation occurs exclusively following attack of the nitrating cation at the “ipso” position, which promotes intramolecular migration of the alkyl substituent to the nitro group, yielding O-alkylated

  选择的二烷基苯，包括硝化ö和- p -cymene，p -叔-butyltoluene，p -diisopropylbenzene，和p -二-叔丁基苯，通过质子化甲基硝酸盐，（CH 3 OH-NO 2）+，已经研究在气相中的压力范围为10 -8通过傅立叶变换离子回旋共振（FT-ICR）和碰撞活化解离（CAD）质谱法以及通过放射分解技术将其转化为720 Torr。结果首次证明了气相亲电芳族硝基烷基烷基化及其相对于竞争硝化过程的效率的定量评估。脱烷基化仅发生在硝化阳离子在“ ipso”位置发生攻击之后，这会促进烷基取代基向硝基的分子内迁移，从而产生O-烷基化或O-质子化的离子。硝化的位置选择性，以及（CH 3 OH-NO 2）+引起的“ ipso”攻击的相对速率本文讨论了烷基的固有空间需求的作用，烷基在气相中不受溶液中可操作的许多复杂因素（例如溶剂化，离子对等）的影响。将结果与关于缩合氮代烷
• Desseigne, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1935, vol. 200, p. 466
  作者：Desseigne

  DOI：——

  日期：——
• NOVEL BIS-AMIDE DERIVATIVE AND USE THEREOF
  申请人：UNIVERSITY-INDUSTRY COOPERATION GROUP OF KYUNG HEE UNIVERSITY

  公开号：US20160297751A1

  公开（公告）日：2016-10-13

  The present invention relates to a novel bis-amide derivative compound or a pharmaceutically acceptable salt thereof; a method of preparation thereof; and a pharmaceutical composition for preventing or treating diseases caused by hepatitis C virus infection and health functional food for preventing or ameliorating diseases caused by hepatitis C virus infection, containing the bis-amide derivative compound or a pharmaceutically acceptable salt thereof as an active ingredient. The novel bis-amide derivative compound of the present invention, particularly WJCPA-126, specifically binds to the catalytic site of CypA to effectively inhibit the activity of an isomerase, and the duration of the inhibitory effect can be increased because WJCPA-126 binds to CypA with high binding affinity exhibiting a low dissociation rate (K off ). Accordingly, WJCPA-126 has nontoxic and non-immunosuppressive characteristics and can effectively inhibit HCV replication in vitro and in vivo model systems. Additionally, WJCPA-126 reactivates the host interferon response through an increase in the expression of IFN-stimulated genes (ISGs) and the inhibition of interleukin-8 (IL-8) secretion. Therefore, a series of the bis-amide derivatives including WJCPA-126 can be useful as a novel type CypA inhibitor exhibiting antiviral effect.