2-iodo-6-nitrobenzoic acid | 89641-04-3

• 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-iodo-6-nitrobenzoic acid
• CAS: 89641-04-3
• 化学式: C₇H₄INO₄
• 分子量: 293.018
• InChiKey: MYWANTHKKPDBEX-UHFFFAOYSA-N

物化性质

• 熔点：
  188-189 °C
• 沸点：
  386.9±32.0 °C(Predicted)
• 密度：
  2.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-iodo-6-nitrobenzoic acid 在 copper(l) iodide 、 potassium carbonate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 (5-(4,6-dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-nitro-6-(2H-1,2,3-triazol-2-yl)phenyl)methanone
  参考文献：
  名称：

  Synthesis and characterization of a new Positron emission tomography probe for orexin 2 receptors neuroimaging

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105779
• 作为产物：
  描述：

  2-氨甲酰基-6-硝基苯甲酸 在 alkaline aqueous sodium hypochlorite 作用下， 生成 2-iodo-6-nitrobenzoic acid
  参考文献：
  名称：

  230.乌尔曼法合成中观苯并蒽酮和蒽酮

  摘要：

  DOI：

  10.1039/jr9370001096

文献信息

• Base- and Additive-Free Ir-Catalyzed <i>ortho</i>-Iodination of Benzoic Acids: Scope and Mechanistic Investigations
  作者：Elis Erbing、Amparo Sanz-Marco、Ana Vázquez-Romero、Jesper Malmberg、Magnus J. Johansson、Enrique Gómez-Bengoa、Belén Martín-Matute

  DOI：10.1021/acscatal.7b02987

  日期：2018.2.2

  A protocol for the C–H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture

  已经开发了一种由简单铱络合物催化的苯甲酸的C–H活化/碘化的方案。本文描述的方法允许在非常温和的条件下，在没有任何添加剂或碱的情况下，在1,1,1,3,3,3-六氟异丙醇作为溶剂中对多种苯甲酸进行邻位碘化。所用的铱催化剂可耐受空气和湿气，并选择性地以高转化率得到邻碘苯甲酸。机理研究表明，Ir（III）/ Ir（V）催化循环起作用，并且HFIP的独特性质使得能够使用羧基作为引导基团进行C-H碘化。
• NOVEL COMPOUNDS AS CHLORIDE CHANNEL BLOCKING AGENT
  申请人：Korea Institute of Science and Technology

  公开号：US20150148550A1

  公开（公告）日：2015-05-28

  Disclosed is a novel compound to function as a calcium-dependent chloride channel blocking agent.

  披露了一种新型化合物，用作钙依赖性氯离子通道阻滞剂。
• Pd-Catalyzed Decarboxylative <i>Ortho</i>-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group
  作者：Zhengjiang Fu、Yongqing Jiang、Shuiliang Wang、Yuanyuan Song、Shengmei Guo、Hu Cai

  DOI：10.1021/acs.orglett.9b00460

  日期：2019.5.3

  A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C–H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated

  建立了在好氧条件下廉价的邻硝基苯甲酸与NaX（X = I，Br）的高区域选择性Pd催化的Pd催化的羧基定向脱羧邻C-H卤代反应。该方法的实用性已通过克级反应和产物衍生化得到证明。实验结果证实，Pd和Bi在转化中起关键作用，并表明该转化可能通过2-卤代6-硝基苯甲酸衍生物中间体进行。
• Chemometric Analysis of Substituent Effects. XI. Solvent Effects on Dissociation of 2,6-Disubstituted Benzoic Acids
  作者：Jiří Kulhánek、Oldřich Pytela

  DOI：10.1135/cccc19970913

  日期：——

  Eleven symmetrically 2,6-disubstituted benzoic acids (with the following substituents: OCH₃, OC₂H₅, OC₃H₇, OCH(CH₃)₂, OC₄H₉, CH₃, F, Cl, Br, I, and NO₂) have been synthesized and their dissociation constants measured potentiometrically in methanol, ethanol, propan-1-ol, propan-2-ol, butan-2-ol, acetone, dimethyl sulfoxide, dimethylformamide, acetonitrile, pyridine, and 1,2-dichloroethane. The experimental data obtained have been analyzed from the point of view of solvent effects on acidity of the individual derivatives. Different behaviour found with benzoic acid and the disubstituted derivatives in protic solvents is due to changes in solvation. The different character of solvation of benzoic acid and the disubstituted derivatives depends on the type of substitution, being manifested only in 2,6-disubstituted benzoic acids. The graphical analysis has shown a distinct trend in the increase of magnitude of deviation of the point of benzoic acid in the series: propan-2-ol, butan-2-ol, propan-1-ol, ethanol, methanol. This order correlates with the steric demands of carbon chain of the alcohols used. The abnormal behaviour of benzoic acid in the dissociation in these alcohols as compared with that of its 2,6-disubstituted derivatives is due to the different extent of solvation of the reaction centre caused by steric hindrance. Against the expectation, benzoic acid appears to be a weaker acid in protic solvents, whereas its alkoxy derivatives are stronger acids. The solvation also minimizes the inductive effect of alkoxy groups in the symmetrically 2,6-disubstituted derivatives. In aprotic solvents the acidity of 2,6-dialkoxybenzoic acids is also increased, in this case as a result of sterically forced deviation of the reaction centre and/or the substituents out of the plane of benzene ring.

  已合成了十一个对称的2,6-二取代苯甲酸（具有以下取代基：OCH₃、OC₂H₅、OC₃H₇、OCH(CH₃)₂、OC₄H₉、CH₃、F、Cl、Br、I和NO₂），并在甲醇、乙醇、1-丙醇、2-丙醇、2-丁醇、丙酮、二甲基亚砜、二甲基甲酰胺、乙腈、吡啶和1,2-二氯乙烷中测量了它们的电位滴定解离常数。从溶剂对各个衍生物酸度的影响角度分析了所得到的实验数据。在质子溶剂中，苯甲酸和二取代衍生物的不同行为是由于溶剂化的改变。苯甲酸和二取代衍生物的不同溶剂化特性取决于取代类型，仅在2,6-二取代苯甲酸中表现出来。图形分析显示出苯甲酸点的偏离程度在以下系列中呈现出明显的趋势：2-丙醇、2-丁醇、1-丙醇、乙醇、甲醇。这个顺序与所使用醇类的碳链的空间位阻有关。与其2,6-二取代衍生物相比，在这些醇中苯甲酸的解离行为异常，这是由于空间位阻引起的反应中心溶剂化程度不同。与预期相反，苯甲酸在质子溶剂中似乎是较弱的酸，而其烷氧基衍生物是较强的酸。溶剂化还使对称的2,6-二烷氧基苯甲酸中烷氧基群的感应效应最小化。在无质子溶剂中，2,6-二烷氧基苯甲酸的酸度也增加了，这是由于反应中心和/或取代基被迫离开苯环平面的空间位阻造成的。
• Activated iododerivatives for the treatment of cancer and aids
  申请人：——

  公开号：US20020019538A1

  公开（公告）日：2002-02-14

  A series of activated iodo-benzamide derivatives are described as antineoplastic and antiviral drug compounds. The compounds generally possess a chelating group, a thiol trapping group and an activating group. The presumptive mechanism of action in preventing cancer cell and virus replication is through inhibition of the binding of transcription factors to zinc finger binding domains. The compounds are effective in inhibiting growth of a variety of human and animal tumor and leukemia cell lines at low concentrations.

  一系列激活的碘苯酰胺衍生物被描述为抗肿瘤和抗病毒药物化合物。这些化合物通常具有螯合基团、硫醇捕捉基团和活化基团。预计抑制癌细胞和病毒复制的作用机理是通过抑制转录因子与锌指结合域的结合。这些化合物在低浓度下有效抑制多种人类和动物肿瘤和白血病细胞系的生长。