1-(benzofuran-2-yl)-2-(phenylsulfonyl)ethanone | 144888-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 1-(benzofuran-2-yl)-2-(phenylsulfonyl)ethanone
• 英文别名: 1-(1-benzofuran-2-yl)-2-(phenylsulfonyl)ethanone；2-(benzenesulfonyl)-1-(1-benzofuran-2-yl)ethanone
• CAS: 144888-16-4
• 化学式: C₁₆H₁₂O₄S
• 分子量: 300.335
• InChiKey: OHCULCBYAYIHIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(benzofuran-2-yl)-2-(phenylsulfonyl)ethanone 在 硫酸 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 48.5h， 以52%的产率得到苯并呋喃-2-羧酸
  参考文献：
  名称：

  Oxidative Cleavage ofβ-Keto Sulfones via Nitrous Acid

  摘要：

  硝酸与1-芳基-2-(芳基磺酰基)乙酮酮3a-e反应产生了意外的芳基羧酸12a-e、甲酸14和苯/对甲苯磺酸15a、b，通过氧化裂解反应。4-氯苯甲酸(12a)、[1,1'-联苯]-4-羧酸(12b)、2-萘甲酸(12c)、2-噻吩羧酸(12d)和2-苯并呋喃羧酸(12e)分别以72%、62%、55%、58%和62%的产率分离。报道的机理途径提出了1-芳基-2-(苯基/甲苯基磺酰基)乙烷-1,2-二酮7的产生，而不是芳基羧酸12。提出了一种解释硝酸与1-芳基-2-(芳基磺酰基)乙酮酮3a-e反应的机理途径。在这个途径中，中间体1,2-噁唑烷10失去苯/对甲苯磺酸15，产生1,2-噁唑烷-3-酮11。后者的环裂解产生了芳基羧酸12。

  DOI：

  10.1155/2014/524930
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 在 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 1-(benzofuran-2-yl)-2-(phenylsulfonyl)ethanone
  参考文献：
  名称：

  新型基于苯并呋喃的磺酰胺类作为选择性碳酸酐酶IX和XII抑制剂：合成和体外生物学评估。

  摘要：

  在我们努力寻找有效的hCA IX和hCA XII抑制剂的基础上，我们在此报告了新的基于苯并呋喃的磺酰胺类化合物（4a，b，5a，b，9a-c和10a-d）的设计和合成。通过肼或酰肼连接基连接至苯并呋喃尾的锌锚定苯磺酰胺部分。检查所有目标苯并呋喃对hCA I，II，IX和XII亚型的抑制活性。与靶肿瘤相关的hCA IX和XII同工型分别被KIs有效抑制，其跨度范围为10.0-97.5和10.1-71.8 nM。有趣的是，芳基砜hydr 9在hCA I（SI：分别为39.4-250.3和26.0-149.9）和hCA II（SI：分别为19.6-57.1和13.0-34.2）上显示出对hCA IX和XII的最佳选择性。此外，根据US-NCI协议，评估了目标苯并呋喃对一组六十种癌细胞系的抗增殖活性。仅苯并呋喃5b和10b对某些癌细胞系具有选择性和中等的生长抑制活性。

  DOI：

  10.1080/14756366.2019.1697250

文献信息

• Dual Secondary Amine/N-Heterocyclic Carbene Catalysis in the Asymmetric Michael/Cross-Benzoin Cascade Reaction of β-Oxo Sulfones with Enals
  作者：Dieter Enders、André Grossmann、He Huang、Gerhard Raabe

  DOI：10.1002/ejoc.201100690

  日期：2011.8

  Polyfuncionalized cyclopentanones with three contiguous stereogenic centers were formed in good to excellent yields and stereoselectivities by utilizing a secondary amine/N-heterocyclic carbene catalytic system in the reaction of β-oxo sulfones with unsaturated aldehydes. In addition, the influence of the catalysts on the diastereoselectivity of the final product was studied by 1H NMR spectroscopy

  通过在β-氧代砜与不饱和醛的反应中利用仲胺/N-杂环卡宾催化体系，以良好至极好的收率和立体选择性形成具有三个连续立体中心的多官能化环戊酮。此外，通过 1 H NMR 光谱研究了催化剂对最终产物的非对映选择性的影响。
• Transition-Metal-Free Approach to Polysubstituted Furans
  作者：Changming You、Zhenming Zhang、Yongliang Tu、Hong Tang、Yuanfeng Wang、Da Long、Junfeng Zhao

  DOI：10.1021/acs.joc.9b03006

  日期：2020.3.6

  A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of β-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance

  描述了一种通过β-酮化合物与二氯乙烯的碱促进的多米诺反应合成2,3-二取代和2,3,5-三取代的呋喃的便捷方法。这种无过渡金属的方法在操作简单的反应条件下进行，该条件具有容易获得的起始原料，广泛的底物范围和良好的官能团耐受性。
• Dual-tail arylsulfone-based benzenesulfonamides differently match the hydrophobic and hydrophilic halves of human carbonic anhydrases active sites: Selective inhibitors for the tumor-associated hCA IX isoform
  作者：Hany S. Ibrahim、Heba Abdelrasheed Allam、Walaa R. Mahmoud、Alessandro Bonardi、Alessio Nocentini、Paola Gratteri、Eslam S. Ibrahim、Hatem A. Abdel-Aziz、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2018.04.016

  日期：2018.5

  The synthesis and characterization of two new sets of arylsulfonehydrazone benzenesulfonamides (4a-4i with phenyl tail and 4j-4q with tolyl tail) are reported. The compounds were designed according to a dual-tails approach to modulate the interactions of the ligands portions at the outer rim of both hydrophobic and hydrophilic active site halves of human isoforms of carbonic anhydrase (CA, EC 4.2.1.1). The synthesized sulfonamides were evaluated in vitro for their inhibitory activity against the following human (h) isoforms, hCA I, II, IV and IX. With the latter being a validated anticancer drug target and a marker of tumor hypoxia, attractive results arose from the Compounds' inhibitory screening in terms of potency and selectivity. Indeed, whereas the first subset of compounds 4a-4i exhibited great efficacy in inhibiting both the ubiquitous, off-target hCA II (K(l)s 9.5-172.0 nM) and hCA IX (Kis 7.5-131.5 nM), the second subset of tolyl-bearing derivatives 4j-4q were shown to possess a selective hCA IX inhibitory action over isoforms I, II and IV. The most selective compounds 41 and 4n were further screened for their in vitro cytotoxic activity against MCF-7 and MDA-MB-231 cancer cell lines under hypoxic conditions. The selective IX/II inhibitory trend of 4j-4q compared to those of compounds 4a-4i was unveiled by docking studies. Further exploration of these molecules could be useful for the development of novel antitumor agents with a selective CA inhibitory mechanism. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Method for preparing carboxylic acids
  申请人：King Saud University

  公开号：EP2930164B1

  公开（公告）日：2016-03-23
• US9018399B1
  申请人：——

  公开号：US9018399B1

  公开（公告）日：2015-04-28