ethyl azulene-2-carboxylate | 1119108-35-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: ethyl azulene-2-carboxylate
• 英文别名: ethyl 2-azulenecarboxylate
• CAS: 1119108-35-8
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: QUXMQIOEVUMQCT-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  308.1±10.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  azulene-2-boronic acid 、 氯甲酸乙酯 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以50%的产率得到ethyl azulene-2-carboxylate
  参考文献：
  名称：

  An Easy Access to 2-Substituted Azulenes from Azulene-2-boronic Acid Pinacol Ester

  摘要：

  利用阿杂蒽-2-硼酸频哪醇酯能够方便地转化为难以通过常规方法获得的具有羧基、醛基、酯基或氨基的2-取代阿杂蒽衍生物。此外，通过上述合成的阿杂蒽-2-羧酸进一步进行Ugi四组分缩合反应，获得了一种含有阿杂蒽骨架的二肽型产物。

  DOI：

  10.1055/s-0028-1083224

文献信息

• [EN] PIPERAZINE SUBSTITUTED ARYL BENZODIAZEPINES<br/>[FR] ARYL BENZODIAZEPINES SUBSTITUEES PAR DE LA PIPERAZINE
  申请人：LILLY CO ELI

  公开号：WO2004014895A1

  公开（公告）日：2004-02-19

  Described herein are compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, S, and O; Alk is (C1-4) alkylene or hydroxy substituted (C1-4) alkylene; X is oxygen or sulfur; R1 is hydrogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, or (C1-4) alkyl, wherein the (C1-4) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH2CH2OH, or -CN; R2 is H, halogen, (C1-6) fluoroalkyl, (C1-6) cycloalkyl, OR4, SR4, N02, CN, COR4, C(O)OR4, CONR5R6 , NR5R6, S02NR5R6, NR5COR4, NR5SO2R4, optionally substituted aromatic, or (C1-6) alkyl, wherein (C1-6) alkyl is unsubstituted or substituted with a hydroxy group; R3 is hydrogen, (C1-6) fluoroalkyl, (C2-6) alkenyl, Ar, (C1-4)alkyl-Ar, or (C1-4) alkyl wherein (C1-4) alkyl is unsubsituted or substituted with a phenyl; R4 is hydrogen, (C1-6 alkyl, (C1-6) fluoroalkyl, or optionally substituted aromatic; R5 and R6 are independently hydrogen, (C1-6) alkyl, or optionally substituted aromatic, R7 is hydrogen, (C1-6) alkyl, (C1-6) fluoroalkyl, or optionally substituted aromatic; R8 and R9 are independently hydrogen, (C1-6) alkyl, or optionally substituted aromatic; Ar is optionally substituted phenyl, napthyl, monocyclic heteroaromatic or bicyclic heteroaromatic; Z1 and Z2 are independently selected from hydrogen, halogen, (C1-6) alkyl, (C1-6) fluoroalkyl, OR7, SR7, NO2, CN, COR7, CONR8R9, NR8R9, and optionally substituted aromatic; and all salts, solvates, optical and geometric isomers, and crystalline forms thereof. Also, described are the use of the compounds of formula (I) as antagonists of the dopamine D2 receptor and as agents for the treament of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I).

  本文描述了以下式(I)的化合物：其中：是一个可选的苯并嵌合的五元或六元芳香环，其中含有从N、S和O中独立选择的零至三个杂原子；Alk是(C1-4)烷基或羟基取代的(C1-4)烷基；X是氧或硫；R1是氢、(C1-6)氟烷基、(C3-6)环烷基或(C1-4)烷基，其中(C1-4)烷基未取代或取代为羟基、甲氧基、乙氧基、OCH2CH2OH或-CN；R2是H、卤素、(C1-6)氟烷基、(C1-6)环烷基、OR4、SR4、N02、CN、COR4、C(O)OR4、CONR5R6、NR5R6、S02NR5R6、NR5COR4、NR5SO2R4、可选取代的芳香基或(C1-6)烷基，其中(C1-6)烷基未取代或取代为羟基；R3是氢、(C1-6)氟烷基、(C2-6)烯基、Ar、(C1-4)烷基-Ar或(C1-4)烷基，其中(C1-4)烷基未取代或取代为苯基；R4是氢、(C1-6)烷基、(C1-6)氟烷基或可选取代的芳香基；R5和R6独立地是氢、(C1-6)烷基或可选取代的芳香基，R7是氢、(C1-6)烷基、(C1-6)氟烷基或可选取代的芳香基；R8和R9独立地是氢、(C1-6)烷基或可选取代的芳香基；Ar是可选取代的苯基、萘基、单环杂芳基或双环杂芳基；Z1和Z2独立地选自氢、卤素、(C1-6)烷基、(C1-6)氟烷基、OR7、SR7、NO2、CN、COR7、CONR8R9、NR8R9和可选取代的芳香基；以及其所有盐、溶剂化合物、光学和几何异构体以及结晶形式。此外，还描述了将上述式(I)的化合物用作多巴胺D2受体拮抗剂以及用于治疗精神病和双相情感障碍的药剂，以及上述式(I)的药物配方。
• EPR Studies on Carboxylic Esters, 22 [1, 2]. Preparation of New Alkyl Azulenecarboxylates and EPR-spectroscopic Study of Their Radical Anions
  作者：Jürgen Voss、Thomas Pesel、Dirk Buddensiek、Juuso Lehtivarjo

  DOI：10.5560/znb.2014-3303

  日期：2014.4.1

  Five regio-isomeric alkyl azulenecarboxylates were prepared. Additional substituents such as tertbutyl groups or deuterium were introduced in certain positions of the azulene skeleton in order to facilitate the assignment of the proton hyperfine structure (hfs) coupling constants of the EPR spectra. The electrochemical behavior of the esters was studied by means of differential pulse polarography and cyclovoltammetry. In-situ electroreduction of the azulenecarboxylic esters led to the corresponding radical anions, the EPR spectra of which were recorded. The spin density distribution in these non-alternant systems as determined from hfs coupling constants was compared with the results of MO calculations and discussed with respect to the influence of substituents.

  制备了五种烷基偶氮烯羧酸异构体。在氮烯骨架的某些位置引入了额外的取代基，如叔丁基或氘，以便于确定 EPR 光谱的质子超精细结构（hfs）耦合常数。通过微分脉冲极谱法和环形伏安法研究了这些酯的电化学行为。偶氮羧酸酯的原位电还原产生了相应的自由基阴离子，并记录了其 EPR 光谱。根据 hfs 耦合常数确定的这些非互变体系的自旋密度分布与 MO 计算的结果进行了比较，并讨论了取代基的影响。
• [EN] THIADIBENZOAZULENE DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] DERIVES DE THIADIBENZOAZULENE POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2004078763A1

  公开（公告）日：2004-09-16

  The present invention relates to novel 1-thia-dibenzoazulene derivatives of the formula (I), wherein X individually denotes a hetero atom -O- or -S-; Y and Z independently from each other individually denote a fragment of the formula (II) to their pharmacologically acceptable esters, salts and solvates, to processes and intermediates for the preparation thereof, to a process for preparing pharmaceutical formulations for the treatment of inflammatory diseases and conditions and to the use thereof in the treatment of inflammatory diseases and conditions in humans and animals. These compounds inhibit tumour necrosis factor-α(TNF-(α) production and interleukin-1 (IL-1) production and exhibit an analgetic action.

  本发明涉及新颖的1-硫代二苯并蓝烯衍生物的公式(I)，其中X分别表示杂原子-O-或-S-；Y和Z独立地分别表示公式(II)的片段及其药理学上可接受的酯、盐和溶剂，以及用于制备它们的过程和中间体，用于制备用于治疗炎症性疾病和症状的药物配方的过程，以及在人类和动物中治疗炎症性疾病和症状中的使用。这些化合物抑制肿瘤坏死因子-α（TNF-α）的产生和白细胞介素-1（IL-1）的产生，并表现出镇痛作用。
• PIPERAZINE SUBSTITUTED ARYL BENZODIAZEPINES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1546134A1

  公开（公告）日：2005-06-29
• THIADIBENZOAZULENE DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：PLIVA-ISTRAZIVACKI INSTITUT d.o.o.

  公开号：EP1603921A1

  公开（公告）日：2005-12-14