methyl 4-(azidocarbonyl)benzoate | 173458-34-9

• 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: methyl 4-(azidocarbonyl)benzoate
• 英文别名: 4-azidocarbonyl-benzoic acid methyl ester；terephthalic acid-azide-methyl ester；Terephthalsaeure-azid-methylester；4-carbomethoxybenzoyl azide；(1Z)-N-diazonio-4-methoxycarbonylbenzenecarboximidate
• CAS: 173458-34-9
• 化学式: C₉H₇N₃O₃
• 分子量: 205.173
• InChiKey: KJVMPAIRIMCGBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(azidocarbonyl)benzoate 以 甲苯 为溶剂， 反应 2.0h， 生成 4-异氰酰基苯甲酸甲酯
  参考文献：
  名称：

  Tyrosine Kinase Inhibitors. 4. Structure-Activity Relationships among N- and 3-Substituted 2,2'-Dithiobis(1H-indoles) for in vitro Inhibition of Receptor and Nonreceptor Protein Tyrosine Kinases

  摘要：

  A series of S-substituted 2,2'-dithiobis(1H-indoles) were synthesized and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase, to extend the available structure-activity relationships for this series. The majority of the compounds were prepared either by reaction of 2-chloro-1-methylindole-3-carbonyl chloride with amines, followed by thiomethylation, demethylation, and oxidative dimerization, or by reaction of isocyanates with the anion of 1-methyl-2-indolinethione followed by dimerization. Overall, inhibitory activity is retained by analogues having a wide variety of side chains. A series of 3-carboxamide analogues had moderate to good activity against isolated EGFR (IC(50)s 1-20 mu M), with monoalkyl substitution of the carboxamide being optimal. Polar side chains were generally less effective than lipophilic ones, with benzyl being particularly effective. However, N,N-disubstitution was the most effective pattern for inhibition of pp60(v-src). A variety of substituted N-phenylcarboxamides had lower activity against EGFR than the parent derivative, and a N-thienylcarboxamide also had low activity. A series of 3-ketones, including methyl, phenyl, and furyl derivatives, showed moderate activity against the pp60(v-src) kinase, but were less effective against EGFR. The mechanism of inhibition of both kinases by these drugs was shown to be noncompetitive with respect to both ATP and peptide substrate. Selected compounds inhibited the growth of Swiss 3T3 cells with IC(50)s in the low micromolar range and inhibited bFGF-mediated intracellular tyrosine phosphorylation in the same cell line. Thiol inhibits the effects of the compounds, suggesting that one possible mechanism of inhibition is thiol-disulfide exchange with thiol-containing residues in the catalytic sites. Crystal structures of two representative compounds show a folded, V-shaped structure, with the disulfide bridge exposed, consistent with this hypothesis.

  DOI：

  10.1021/jm00001a011
• 作为产物：
  描述：

  对甲酰基苯甲酸甲酯 在 sodium azide 、 三氯异氰尿酸 、 苄基三乙基氯化铵 作用下， 反应 1.0h， 生成 methyl 4-(azidocarbonyl)benzoate
  参考文献：
  名称：

  苯甲醇一锅转化为 N-保护苯胺和烷基醇转化为氨基甲酰叠氮化物

  摘要：

  无需浪费溶剂交换和后处理操作，开发了一种优化的可扩展反应序列（高达 83%），用有价值的氮官能团取代伯醇的羟甲基（R=取代的苯基或烷基）。一种经济、绿色的时尚。

  DOI：

  10.1002/ejoc.202300786

文献信息

• Visible light sensitization of benzoyl azides: cascade cyclization toward oxindoles via a non-nitrene pathway
  作者：Dattatraya B. Bagal、Sung-Woo Park、Hyun-Ji Song、Sukbok Chang

  DOI：10.1039/c7cc04852a

  日期：——

  Visible light sensitization of benzoyl azides was examined in reaction with N-phenylmethacrylamides to afford biologically important oxindoles and spirooxindoles via a cascade cyclization under mild reaction conditions. Mechansitic studies suggested a non-nitrene pathway, where triplet benzoyl azides act as the reactive intermediate.

  在N-苯基甲基丙烯酰胺反应下，通过级联环化在温和的反应条件下，对苯甲酰叠氮化物的可见光敏化进行了检测，从而提供了生物学上重要的羟吲哚和螺氧并吲哚。力学研究表明，非三烯途径中，三重态苯甲酰叠氮化物充当反应性中间体。
• Oxidative Amidation and Azidation of Aldehydes by NHC Catalysis
  作者：Suman De Sarkar、Armido Studer

  DOI：10.1021/ol1004643

  日期：2010.5.7

  N-Heterocyclic carbene catalyzed oxidative amidations of various aldehydes to the corresponding hexafluoroisopropylesters by using the readily available organic oxidant A are described. The hexafluoroisopropylesters prepared in situ are shown to be highly useful active esters for amide bond formation. In addition, oxidative azidation of aldehydes is presented. These mild organocatalytic processes do not use any

  描述了通过使用容易获得的有机氧化剂A的N-杂环卡宾催化的各种醛向相应的六氟异丙基酯的氧化酰胺化。已显示原位制备的六氟异丙基酯是用于酰胺键形成的高度有用的活性酯。另外，提出了醛的氧化叠氮化。这些温和的有机催化过程不使用任何过渡金属。
• Pd-Catalyzed Carbonylation of Acyl Azides
  作者：Zongyang Li、Shiyang Xu、Baoliang Huang、Chenhui Yuan、Wenxu Chang、Bin Fu、Lei Jiao、Peng Wang、Zhenhua Zhang

  DOI：10.1021/acs.joc.9b01048

  日期：2019.8.2

  provides facile access to acyl ureas. In addition, a mechanistic study was carried out by both experiment and DFT calculation. Control experiments and kinetic study revealed that the real active palladium species were Pd(0). The result of kinetic study suggested that palladium catalyst, azide, and CO were all involved in the turnover-limiting step except for amine. Further DFT study suggested that an

  近年来，已广泛开发了Pd催化的叠氮化物与CO反应生成异氰酸酯中间体的方法。然而，尚未报道敏感的酰基叠氮化物的催化羰基化。在本文中，我们报道了酰基叠氮化物的简单Pd催化羰基化反应，具有广泛的底物范围，高效率以及在温和条件下的简单操作，可轻松获得酰基脲。此外，还通过实验和DFT计算进行了机理研究。对照实验和动力学研究表明，真正的活性钯物质为Pd（0）。动力学研究的结果表明，除胺外，钯催化剂，叠氮化物和一氧化碳都参与了营业额限制步骤。
• 2-thioindoles (selenoindoles) and related disulfides (selenides) which
  申请人：Warner-Lambert

  公开号：US05464861A1

  公开（公告）日：1995-11-07

  2-Thioindoles (2-selenoindoles) and analogous 2-indolinethione (2-indolineselenone) and polysulfide (selenide) compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds, and methods for inhibiting protein kinase dependent disease in a mammal or treating aberrant cell growth in a mammal, using said compositions, are disclosed.

  本文揭示了2-硫代吲哚（2-硒代吲哚）及类似的2-吲哚硫酮（2-吲哚硒酮）和聚硫化物（硒化物）化合物，以及其盐、生产方法、生产中间体、含有该类化合物的药物组合物，以及使用这些组合物来抑制蛋白激酶依赖性疾病或治疗哺乳动物中的异常细胞生长的方法。
• Reaction of Amide and Sodium Azide for the Synthesis of Acyl Azide, Urea, and Iminophosphorane
  作者：Devaneyan Joseph、Sunwoo Lee

  DOI：10.1021/acs.orglett.2c02429

  日期：2022.8.26

  in DMF at 25 °C and produce the symmetrical ureas in THF/H2O at 80 °C via the sequential reaction of acyl substitution and Curtius rearrangement. All acyl azides were also obtained from the secondary amides via sequential reaction of p-toluenesulfonyl chloride and NaN3. In addition, keto-stabilized iminophosphoranes were prepared from a one-pot reaction of amides, NaN3, and phosphines.

  酰胺与 NaN 3在 25 °C 下在 DMF 中反应生成酰基叠氮化物，并在 80 °C 下通过酰基取代和 Curtius 重排的顺序反应在 THF/H 2 O 中生成对称脲。所有的酰基叠氮化物也是由仲酰胺通过对甲苯磺酰氯和NaN 3 的顺序反应得到的。此外，由酰胺、NaN 3和膦的一锅法反应制备了酮基稳定的亚氨基正膦。