ethyl 4-(4-bromobutoxy)benzoate | 160390-05-6

• 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: ethyl 4-(4-bromobutoxy)benzoate
• CAS: 160390-05-6
• 化学式: C₁₃H₁₇BrO₃
• 分子量: 301.18
• InChiKey: BQNLPYCUFRUDAL-UHFFFAOYSA-N

物化性质

• 沸点：
  386.5±22.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-bromobutoxy)benzoate 在 sodium periodate 、 copper(l) iodide 、 lithium methanolate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.08h， 生成 (4-(4-(ethoxycarbonyl)phenoxy)butyl)boronic acid
  参考文献：
  名称：

  铜催化的伯和仲烷基硼酸的三氟甲基硫醇化

  摘要：

  描述了用亲电子的三氟甲基硫醇化试剂的Cu催化的伯烷基硼酸和仲烷基硼酸的三氟甲基硫醇化。观察到对各种官能团的耐受性。

  DOI：

  10.1021/ol502132j
• 作为产物：
  描述：

  1,4-二溴丁烷 、 过氧化氢酶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以72%的产率得到ethyl 4-(4-bromobutoxy)benzoate
  参考文献：
  名称：

  Nipagin-Functionalized Porphyrazine and Phthalocyanine—Synthesis, Physicochemical Characterization and Toxicity Study after Deposition on Titanium Dioxide Nanoparticles P25

  摘要：

  Aza-卟啉类化合物在紫外-可见光谱中表现出独特的光谱特性，它们在医学中作为光敏剂以及在技术中作为催化剂等应用中得到研究。通过使用适当的外围取代基可以调节它们的物理化学性质。合成并使用UV-Vis和NMR光谱以及质谱对4-(丁氧羰基)苯氧基取代的酞菁和硫醚卟啉八取代物进行了表征。将酞菁和硫醚卟啉类化合物与Aza-卟啉类化合物进行比较，发现酞菁大环具有更高的单线态氧生成量子产率，在DMF中达到0.29。将两种大环沉积在二氧化钛纳米颗粒P25上后，使用Microtox®急性毒性测试研究了所制备材料的细胞毒性和光细胞毒性。在红光照射后，沉积在二氧化钛纳米颗粒上的酞菁材料表现出最高的细胞毒性。

  DOI：

  10.3390/molecules26092657

文献信息

• Synthesis, characterisation, electronic spectra and electrochemical investigation of ferrocenyl-terminated dendrimers
  作者：Carolina Villalonga-Barber、Kalliopi Vallianatou、Spyros Georgakopoulos、Barry R. Steele、Maria Micha-Screttas、Efrat Levin、N. Gabriel Lemcoff

  DOI：10.1016/j.tet.2013.03.047

  日期：2013.5

  Two new dodecaferrocenyl dendrimers have been prepared using a sixfold Sonogashira coupling reaction and sixfold Huisgen cycloaddition, respectively. In addition, a dendron containing four ferrocenyl groups has been synthesised by conventional synthetic methods. Electrochemical studies have shown that all the ferrocene units are electrochemically equivalent. Moreover, when treated with acid these compounds

  分别使用六倍的Sonogashira偶联反应和六倍的Huisgen环加成反应制备了两种新的十二碳二茂铁基树枝状聚合物。另外，已经通过常规合成方法合成了包含四个二茂铁基的树枝状分子。电化学研究表明，所有二茂铁单元在电化学上都是等效的。而且，当用酸处理时，这些化合物形成了具有高消光系数的多电荷的甲基化近红外吸收性树枝状染料。
• Nucleophilic Trifluoromethylthiolation of Alkyl Chlorides, Bromides and Tosylates
  作者：Chunfa Xu、Qingyun Chen、Qilong Shen

  DOI：10.1002/cjoc.201500905

  日期：2016.5

  A direct nucleophilic trifluoromethylthiolation of alkyl chlorides, bromides and tosylates with AgSCF3 was described. It was found that the presence of nBu4NI or a combination of nBu4NI/nBu4NBr significantly enhanced the reaction rates. The reaction conditions were mild, thus allowing the tolerance of a variety of functional groups.

  描述了用AgSCF 3烷基氯，溴化物和甲苯磺酸酯的直接亲核三氟甲基硫醇化。发现存在n Bu 4 NI或n Bu 4 NI / n Bu 4 NBr的组合显着提高了反应速率。反应条件温和，因此允许各种官能团的耐受性。
• Structure-Activity Relationship Studies of 1-Substituted 3-Dodecanoylindole-2-carboxylic Acids as Inhibitors of Cytosolic Phospholipase A2-Mediated Arachidonic Acid Release in Intact Platelets
  作者：Klaus Griessbach、Monika Klimt、Alwine Schulze Elfringhoff、Matthias Lehr

  DOI：10.1002/ardp.200290008

  日期：2002.12

  A series of 3‐dodecanoylindole‐2‐carboxylic acid derivatives with varied carboxylic acid substituents at the indole 1‐position were synthesized and evaluated for their ability to inhibit arachidonic acid release in human platelets mediated by the cytosolic phospholipase A2. Structure‐activity relationship studies revealed that increasing the polarity of these substituents by the introduction of additional

  合成了一系列在吲哚 1-位具有不同羧酸取代基的 3-十二酰基吲哚-2-羧酸衍生物，并评估了它们抑制细胞溶质磷脂酶 A2 介导的人血小板中花生四烯酸释放的能力。构效关系研究表明，通过在羧酸部分附近引入额外的极性基团来增加这些取代基的极性会降低活性。吲哚-1-羧酸替代物在不同位置的构象限制以及这些残基的长度延长导致化合物的效力没有显着差异。
• Design, synthesis, biological evaluation and molecular dynamics simulation studies of (R)-5-methylthiazolidin-4-One derivatives as megakaryocyte protein tyrosine phosphatase 2 (PTP-MEG2) inhibitors for the treatment of type 2 diabetes
  作者：Jingwei Wu、Yingzhan Sun、Hui Zhou、Ying Ma、Runling Wang

  DOI：10.1080/07391102.2019.1654410

  日期：2020.7.23

  PTP-MEG2 plays a significant role in insulin production and is able to enhance insulin signaling and improve insulin sensitivity. So, PTP-MEG2 inhibitors are closely associated with type 2 diabetes therapy. A series of novel (R)-5-methylthiazolidin-4-one derivatives were designed and synthesized, and their PTP-MEG2 inhibitory activities (IC50) were determined. Among the desired compounds, 1h shares the highest inhibitory activity (IC50 = 1.34 mu M) against PTP-MEG2. Additionally, various post-dynamic analyses confirmed that when compound 1h bound to the PTP-MEG2, the protein conformations became unstable and the function of the pTyr recognition loop (Asn331-Cys338) would be disturbed. And thus, the ideal conformations needed for the catalytic activity was difficult to be maintained. In brief, these might be how the compound 1h worked. Furthermore, we also found that the key residues Arg332 would play a critical role in disturbing the residue interactions.
• Novel 3-dodecanoylindole-2-carboxylic acid inhibitors of cytosolic phospholipase A2
  作者：Matthias Lehr、Monika Klimt、Alwine Schulze Elfringhoff

  DOI：10.1016/s0960-894x(01)00472-3

  日期：2001.10

  Derivatives of 1-[2-(4-carboxyphenoxy)ethyl]-3-dodecanoylindole-2-carboxylic acid (4) with modified substituents at the indole-1-position were synthesized and evaluated for their ability to inhibit the arachidonic acid release in human platelets mediated by the cytosolic phospholipase A(2). One of the most active compounds obtained was 26 with an IC50 of 0.44 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.