1-Thienyl-3-(o-bromophenyl)-propen-3-one | 4992-43-2

• 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: 1-Thienyl-3-(o-bromophenyl)-propen-3-one
• 英文别名: 1-(2-bromophenyl)-3-thiophen-2-ylprop-2-en-1-one
• CAS: 4992-43-2
• 化学式: C₁₃H₉BrOS
• 分子量: 293.184
• InChiKey: LSUMKAYVELUSBE-UHFFFAOYSA-N

物化性质

• 熔点：
  31 °C(Solv: methanol (67-56-1); ligroine (8032-32-4))
• 沸点：
  413.5±45.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-Thienyl-3-(o-bromophenyl)-propen-3-one 在 copper diacetate 、 potassium ethyl xanthogenate 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 生成 2-(thiophen-2-yl)thiochroman-4-one
  参考文献：
  名称：

  铜催化一锅法合成2-芳基硫代色酮：废副产物的原位循环作为有用的试剂

  摘要：

  使用黄原酸酯作为无味硫源，从容易获得的2'-卤代al烯中开发了铜催化的一锅合成各种2-芳基硫代色酮。该方法论证明了使用第一步的副产物（KI）作为强力氧化剂分子碘（I 2）。这种一锅法合成方法已进一步扩展为使用二甲基亚砜（DMSO）作为溶剂和亚甲基源来合成3,3'-亚甲基双硫黄酮。

  DOI：

  10.1021/acs.orglett.8b03508

文献信息

• Cu-Catalyzed one-pot synthesis of thiochromeno-quinolinone and thiochromeno-thioflavone <i>via</i> oxidative double hetero Michael addition using <i>in situ</i> generated nucleophiles
  作者：Nallappan Sundaravelu、Govindasamy Sekar

  DOI：10.1039/d0cc03210g

  日期：——

  catalyzed three-component synthesis of π-conjugated tetracyclic thiochromeno-quinolinone and thiochromeno-thioflavone was established via oxidative double hetero Michael addition using in situ generated nucleophiles. Xanthate plays a dual role as an odourless sulfur source and a chemoselective reducing agent. The in situ formed iodine plays a crucial role in the oxidation step.

  通过使用原位生成的亲核试剂通过氧化双杂合迈克尔加成反应建立了铜催化的π-共轭四环硫代色氮喹啉酮和硫代色氮硫代黄酮的三组分合成。黄原酸酯起无味硫源和化学选择性还原剂的双重作用。在原位形成碘起着氧化步骤至关重要的作用。
• The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: facile synthesis of benzothiazine derivatives under transition metal-free conditions
  作者：Zheng-Yang Gu、Jia-Jia Cao、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c6sc00240d

  日期：——

  An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed. This protocol provides a new, environment-friendly and simple strategy to construct benzothiazine derivatives via formation of two C–S bonds under transition metal-free, additive-free and oxidant-free conditions. K2S not only provides the sulfur insertion

  通过电子催化，通过K 2 S引发的与烯胺酮的硫插入反应，高效，实用地合成了苯并噻嗪。该协议提供一种新的，环境友好的和简单的策略来构建苯并噻嗪衍生物经由过渡不含金属的，无添加剂和无氧化剂的条件下形成的两个C-S键。K 2 S不仅提供了硫的插入源，而且还通过在DMF中形成三硫自由基阴离子和电子来点燃反应。
• Cu-Catalyzed and iodine mediated synthesis of thioaurones <i>via in situ</i> C–S bond generation using xanthate as a sulfur surrogate
  作者：Palanisamy Soundarya、Govindasamy Sekar

  DOI：10.1039/d2ob01211a

  日期：——

  An efficient method for synthesizing thioaurones has been developed using xanthate as an odorless sulfur surrogate. This reaction's key success lies in the use of iodine as a reagent, which promotes the α-iodination followed by cyclization of saturated ketones. This methodology has also been demonstrated with less reactive 2′-bromochalcones in good yield. Synthesis of the red isomer of indigo, i.e

  已开发出一种使用黄原酸盐作为无味硫代用品的有效合成硫磺酮的方法。该反应的关键成功在于使用碘作为试剂，它促进了 α-碘化，然后是饱和酮的环化。该方法也已通过反应性较低的 2'-溴查耳酮得到良好的收率。还实现了靛蓝的红色异构体的合成，即靛玉红的硫杂类似物。
• New aromatic substituted pyrazoles as selective inhibitors of human adipocyte fatty acid-binding protein
  作者：Xiujie Liu、Xiaoli Huang、Wanhua Lin、Dongye Wang、Yanyan Diao、Honglin Li、Xiaoyan Hui、Yu Wang、Aimin Xu、Donghai Wu、Ding Ke

  DOI：10.1016/j.bmcl.2011.03.063

  日期：2011.5

  a-FABP is indespensible in inflammation and may serve as a new potential drug target for inflammation related diseases. We have successfully designed and synthesized a series of aromatic substituted pyrazoles as new human a-FABP inhibitors. The compounds strongly bound to the hydrophobic binding pocket of a-FABP, while showed significantly lower binding affinities to the closely related homologue protein h-FABP. The most potent and selective compound 5g bound to a-FABP with an apparent K-i value below 1.0 nM, while did not inhibit h-FABP at 50 mu M and thus represents one of the most potent and selective a-FABP inhibitors to date. The strong binding capacity of these inhibitors was further validated by their effective blockade of inflammatory responses as determined by the production of pro-inflammatory cytokines upon LPS stimulation. Compound 5g may serve as a lead compound for developing new effective therapeutic agent for prevention and treatment of atherosclerosis, type 2 diabetes and other inflammatory and metabolic related diseases. (C) 2011 Elsevier Ltd. All rights reserved.