4-(1-咪唑基)苯甲酸乙酯 | 86718-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(1-咪唑基)苯甲酸乙酯
• 英文名称: ethyl 4-(imidazol-1-yl)benzoate
• 英文别名: ethyl 4-(1H-imidazol-1-yl)benzoate；4-imidazol-1-yl-benzoic acid ethyl ester；ethyl 4-imidazol-1-ylbenzoate
• CAS: 86718-07-2
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: JXZSKUXJSZZMON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境中保存

反应信息

• 作为反应物：
  描述：

  4-(1-咪唑基)苯甲酸乙酯 在 sodium tetrahydroborate 、 pyridinium chlorochromate 、 calcium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-(4-甲醛基苯基)咪唑
  参考文献：
  名称：

  Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase

  摘要：

  New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o, m, p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m -substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.

  DOI：

  10.1016/0223-5234(92)90005-l
• 作为产物：
  描述：

  1-(4-甲醛基苯基)咪唑 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(1-咪唑基)苯甲酸乙酯
  参考文献：
  名称：

  N-imidazolyl derivatives of substituted tetrahydrocarbazole and

  摘要：

  本发明提供了新的N-咪唑基取代四氢咔唑和环戊[b]吲哚的衍生物，其一般式为(I)： 其中n为1或2；p为1至4的整数；A为直链或支链C.sub.1-C.sub.4烷基链；B为直接连接，直链或支链，不饱和或饱和的C.sub.1-C.sub.4烷基链；Q为直接连接或直链或支链C.sub.1-C.sub.4烷基链；R.sub.1和R.sub.2各自独立地为氢，C.sub.1-C.sub.4烷基，C.sub.1-C.sub.4烷氧基，C.sub.1-C.sub.4烷硫基，C.sub.1-C.sub.4烷基磺酰基，卤素或三卤甲基；R.sub.3和R.sub.5各自独立地为氢或C.sub.1-C.sub.4烷基；R.sub.4为--OR.sub.6或--N(R.sub.6,R.sub.7)基团，其中R.sub.6和R.sub.7各自独立地为氢，C.sub.1-C.sub.4烷基，苯基或苄基；或其药学上可接受的盐，其在治疗TxA.sub.2合成增强对病态效应的疾病状态中有用。

  公开号：

  US05238953A1

文献信息

• Sulfonamide derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06359134B1

  公开（公告）日：2002-03-19

  The present invention provides compounds which specifically inhibit FXa, which are effective when orally administered and which are useful as a safe medicine for the prevention or treatment of diseases caused by thrombus or infarction. Compounds of this invention are piperazinones of the formula: wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; the ring A is an optionally substituted divalent nitrogen-containing heterocyclic group, in addition to being substituted by the group of the formula: and the group of the formula: Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent heterocyclic group; X is a direct bond or an optionally substituted alkylene chain; Z is (1) an amino group substituted with an optionally substituted hydrocarbon group, (2) an optionally substituted imino group or (3) an optionally substituted nitrogen-containing heterocyclic group; provided that when X is a direct bond and Z is an optionally substituted 6-membered nitrogen-containing aromatic heterocyclic group, Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent unsaturated heterocyclic group; or a salt thereof.

  本发明提供了一种化合物，该化合物特异性地抑制FXa，口服给药有效，并且用作预防或治疗由血栓或梗死引起的疾病的药物是安全的。本发明的化合物是哌嗪酮的公式： 其中R1是可选地取代的烃基或可选地取代的杂环基；环A是除了被公式：的基团取代的之外的可选地取代的二价含氮杂环基： 和公式的基团： Y是可选地取代的二价烃基或可选地取代的二价杂环基；X是直接键或可选地取代的亚烷基链；Z是（1）与可选地取代的烃基取代的氨基，（2）可选地取代的亚氨基或（3）可选地取代的含氮杂环基；当X是直接键并且Z是可选地取代的6-成员含氮芳香杂环基时，Y是可选地取代的二价烃基或可选地取代的二价不饱和杂环基；或其盐。
• pH-Responsive chelating N-heterocyclic dicarbene palladium(ii) complexes: recoverable precatalysts for Suzuki–Miyaura reaction in pure water
  作者：Liuyi Li、Jinyun Wang、Chunshan Zhou、Ruihu Wang、Maochun Hong

  DOI：10.1039/c1gc15312a

  日期：——

  hydrophobic palladium complex of the chelating N-heterocyclic dicarbene (NHDC) (3) was synthesized through in situ deprotonation of a bisimidazolium salt (2) by Pd(OAc)2 in DMSO, subsequent basic hydrolysis and acidification resulted in the formation of four NHDC palladium complexes bearing carboxylic functional groups (4–7). Complexes 4–7 are air-stable, pH-responsive and water-soluble under basic

  螯合N杂环二碳烯（NHDC）（3）的疏水钯配合物是通过双咪唑盐（2）在Pd（OAc）2中的原位脱质子反应合成的。二甲基亚砜，后续基本 水解酸化导致形成四个带有羧基官能团的NHDC钯配合物（4-7）。由于羧基的去质子作用，在碱性条件下，配合物4-7具有空气稳定性，pH响应性和水溶性。使用Suzuki-Miyaura交叉偶联反应对纯净溶液中4-7个亲水性催化体系的催化活性进行了初步评估。水与3种疏水性类似物相比，具有较高的催化活性和化学选择性。催化水溶液或pH响应型催化剂 容易分离，可以回收至少四次。 透射电镜 分析显示Pd（0） 纳米粒子 在催化反应后形成。
• Glucopyranoside-substituted imidazolium-based chiral ionic liquids for Pd-catalyzed homo-coupling of arylboronic acids in water
  作者：Zhonggao Zhou、Jing Li、Yue Wu、Yangyang Yuan、Lingfang Kong、Jun Xue、Zhiqiang Huang

  DOI：10.1080/07328303.2020.1788573

  日期：2020.7.23

  Abstract Chiral ionic liquids (CILs) are widely used solvents and materials with prominent properties. Carbohydrate-derived imidazolium-based CILs represent a distinctive type of CILs possessing multiple chiral centers from natural chiral pool. Herein, a series of glucopyranoside-substituted imidazolium-based CILs (Glu-imi-CILs) were synthesized and evaluated as ligands for Pd-catalyzed homo-coupling

  摘要手性离子液体（CILs）是广泛使用的具有突出性能的溶剂和材料。基于碳水化合物的咪唑鎓类CIL代表了一种独特的CIL类型，具有天然手性库中的多个手性中心。在此，合成了一系列基于吡喃吡喃糖苷取代的咪唑鎓基CIL（Glu-imi-CILs），并将其评估为Pd催化的芳基硼酸在水中均相偶联反应的配体。吡喃葡萄糖苷取代基有助于改善所得催化剂的催化活性。此外，发现具有用于额外配位的游离羟基的Glu-imi-CIL是最有效的配体。用这种方法由芳基硼酸合成了一系列对称的联芳基化合物（13个实例），分离产率高（85-99％）。
• <i>N</i>-Arylation of (hetero)arylamines using aryl sulfamates and carbamates <i>via</i> C–O bond activation enabled by a reusable and durable nickel(0) catalyst
  作者：Iman Dindarloo Inaloo、Sahar Majnooni、Hassan Eslahi、Mohsen Esmaeilpour

  DOI：10.1039/d0nj01610a

  日期：——

  elemental analysis techniques. The reaction proceeded via carbon–oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles

  已经开发出了一种有效且通用的芳基胺化方案，使用了可磁回收的Ni（0）基纳米催化剂。该新型稳定催化剂是在EDTA改性的Fe 3 O 4 @SiO 2上制备的，并通过FT-IR，EDX，TEM，XRD，DLS，FE-SEM，XPS，NMR，TGA，VSM，ICP和元素分析技术进行了研究。该反应通过在简单温和的条件下不使用任何外部配体的情况下，通过（杂）芳基氨基甲酸酯和氨基磺酸酯的碳-氧键裂解来进行。该方法证明了N中的官能团耐受性各种含氮化合物以及脂肪族胺，苯胺，吡咯，吡唑，咪唑，吲哚和吲唑的芳基化，收率良好。此外，该催化剂可以通过使用外部磁场容易地回收，并且可以直接重复使用至少六次而不会显着降低其活性。
• Synthesis of substituted benzo[ij]imidazo[2,1,5-de]quinolizine by rhodium(<scp>iii</scp>)-catalyzed multiple C–H activation and annulations
  作者：Qingmei Ge、Bin Li、Baiquan Wang

  DOI：10.1039/c5ob02515j

  日期：——

  The cascade oxidative annulation reactions of aryl imidazoles with two molecules of alkynes via multiple C–H activation proceed efficiently in the presence of [Cp*RhCl2]2 and Cu(OAc)2·H2O to give substituted benzo[ij]imidazo[2,1,5-de]quinolizine-based polyheteroaromatic compounds. This method is compatible with various functional groups, which are very useful for further synthetic transformations.

  在[Cp * RhCl 2 ] 2和Cu（OAc）2 ·H 2 O的存在下，芳基咪唑与两个炔烃的分子通过多重C–H的级联氧化环化反应有效进行，得到取代的苯并[ ij ]咪唑[2,1,5- de ]喹啉嗪基多杂芳族化合物。该方法与各种官能团兼容，这些官能团对于进一步的合成转化非常有用。