1-(2-bromophenyl)-2,2-dihydroxyethane-1-one | 118888-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-bromophenyl)-2,2-dihydroxyethane-1-one
• 英文别名: 1-(2-Bromophenyl)-2,2-dihydroxyethanone
• CAS: 118888-63-4
• 化学式: C₈H₇BrO₃
• 分子量: 231.046
• InChiKey: MRDMUVZDWDVLLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  328.4±32.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-bromophenyl)-2,2-dihydroxyethane-1-one 在 ammonium hydroxide 、 乙酸酐 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 5.5h， 生成 1-(2-Bromo-phenyl)-4,4,8,8-tetramethyl-2,4,5,7,8,9-hexahydro-3H-pyrrolo[2,3,4-kl]acridin-10-one
  参考文献：
  名称：

  Octahydropyrrolo[4,3,2-m,n]acridine derivatives. 2. 1-Aryl-4,4,8,8-tetramethyl-2,3,4,5,7,8,9,10-octahydropyrrolo[4,3,2-m,n]-acridin-10-ones and intermediates in their synthesis

  摘要：

  DOI：

  10.1007/bf00478862
• 作为产物：
  描述：

  2'-溴苯乙酮 在 selenium(IV) oxide 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 1-(2-bromophenyl)-2,2-dihydroxyethane-1-one
  参考文献：
  名称：

  Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells

  摘要：

  2,2-Dihydroxyarylethanones, readily prepared from the commercially available aromatic ethyl ketones, were reacted with resorcinol, 3-methoxyphenol or 2-methoxyphenol in multi steps one-pot manner promoted by trifluoroacetic acid to furnish the 2,3-diarylbenzofuran derivatives in 22-95% yield. Sixteen targeted compounds were synthesized and characterized by H-1 NMR, C-13 NMR and HRMS. MIT assay indicated that most compounds possessed effectively inhibitory activities against the proliferation of HeLa cell. Among them, 4f had the highest inhibitory activities, with the IC50 being 13.40 +/- 2.04 mu mol/L. Cell cycle analysis, Annexin V-FITC/propidium iodide dual staining assay and western blotting analysis revealed that 4f inhibited the proliferation of Hela cell through apoptosis induction in a dose-dependent manner via obviously up-regulated the levels of Bak and Bim, while striking down regulated the level of Bcl-2 and BcI-xL protein. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.03.010

文献信息

• p-TSA-catalyzed facile and efficient one-pot eco-friendly synthesis of novel isoxazolyl amino furo[3,2-c]quinolinone derivatives in aqueous medium
  作者：Nagi Reddy Modugu、Praveen Kumar Pittala

  DOI：10.1016/j.tetlet.2017.08.062

  日期：2017.10

  operationally simple approach for the synthesis of novel isoxazolyl amino furo[3,2-c]quinolinone derivatives by a one-pot three-component reaction of 4-amino-3-methyl-5 styrylisoxazoles, aryl glyoxal monohydrates and 4-hydroxy-1-methyl-2-quinolinone using p-TSA as the catalyst in aqueous medium was developed. The protocol proves to be an efficient and an environmentally benign in terms of high yields, operational

  通过4-氨基-3-甲基-5苯乙烯基恶唑，芳基乙二醛一水合物和4-水的一锅三组分反应合成新型异恶唑基氨基呋喃[3,2- c ]喹啉酮衍生物的绿色且操作简单的方法以p -TSA为催化剂，在水性介质中开发了羟基-1-甲基-2-喹啉酮。从高产率，操作简便，反应简捷，与各种底物的相容性，水作为溶剂和易于纯化等方面来看，该协议被证明是一种有效且对环境无害的方法。
• 一种合成茚并[2,1-b]吲哚-6(5H)-酮衍生物的方法
  申请人：武汉工程大学

  公开号：CN113620859B

  公开（公告）日：2023-07-18

  本发明涉及一种合成茚并[2,1‑b]吲哚‑6(5H)‑酮衍生物的方法，具体步骤如下：将1‑(2‑溴苯基)‑2,2‑二羟基乙烷‑1‑酮类化合物(a)与2‑吲哚酮类化合物(b)溶于溶剂中，加入碱，在惰性气氛下加热反应，再后处理得到茚并[2,1‑b]吲哚‑6(5H)‑酮衍生物，本发明提供的合成茚并[2,1‑b]吲哚‑6(5H)‑酮衍生物的方法工艺步骤简单，原料简单易得，不涉及过渡金属的使用，制备的产物茚并[2,1‑b]吲哚‑6(5H)‑酮类化合物在药物领域具有应用价值，反应式如下所示：
• Water-acetic acid mediated an efficient and eco-friendly protocol for the one-pot synthesis of bis-isoxazolyl amino dihydro-1 H -indol-4(5 H )-ones under mild reaction conditions
  作者：Modugu Nagi Reddy、Pittala Praveen Kumar

  DOI：10.1016/j.tetlet.2017.11.027

  日期：2017.12

  A cost-effective and eco-friendly straightforward synthesis of new bis-isoxazolyl amino dihydro-1H-indol-4(5H)-ones is successfully achieved via one-pot three-component reaction of N-isoxazolyl enaminone, aryl glyoxal monohydrates and 4-amino-3-methyl-5-styrylisoxazoles by using water as a reaction medium and acetic acid (AcOH) as cheap and green promoter. The protocol proves to be an efficient and

  通过N-异恶唑基烯胺酮，芳基乙二醛一水合物的一锅三组分反应成功地实现了经济高效且环保的新型双-异恶唑基氨基二氢-1 H-吲哚-4（5 H）-酮的合成和4-氨基-3-甲基-5-苯乙烯基恶唑，以水为反应介质，以乙酸（AcOH）为廉价绿色助催化剂。从高产率，低反应时间，操作简便，无金属和广泛的基材范围来看，该协议被证明是一种有效且对环境无害的方法。最重要的是，此反应过程是绿色的。
• Acetic acid promoted an efficient and eco-friendly one-pot synthesis of functionalized novel isoxazolyl amino chromenopyrrole derivatives in aqueous medium
  作者：Nallamothu Vanaja Rani、Ravindhranath Kunta

  DOI：10.1080/00397911.2020.1846058

  日期：2021.2.16

  An efficient, economical, and environmentally friendly method has been reported for one-pot synthesis of isoxazolyl amino chromenopyrrole derivatives from 4-amino-3-methyl-5-styrylisoxazoles, aryl ...

  已经报道了一种高效、经济且环保的方法，用于从 4-氨基-3-甲基-5-苯乙烯基异恶唑、芳基...
• Water-acetic acid mediated an efficient one-pot eco-friendly synthesis of novel bis-isoxazolopyrroloquinoline derivatives
  作者：Sri Venkateswarlu Rayudu、Dipankar Karmakar、Pramod Kumar

  DOI：10.1016/j.tetlet.2019.151025

  日期：2019.9

  An efficient, cost-effective and environmentally benign synthesis of novel tetracyclic bis-isoxazolopyrroloquinoline derivatives has been developed via one-pot four-component reaction of 4-amino-3-methyl-5-styrylisoxazoles, dimedone, aryl glyoxal monohydrates and 5-amino-3-methylisoxazole by employing water as a reaction medium and acetic acid (AcOH) as a green promoter. The advantages of this protocol

  通过4-氨基-3-甲基-5-苯乙烯基恶唑，二甲酮，芳基乙二醛一水合物和5-氨基的一锅四组分反应，开发了一种新型的四环双-异恶唑并吡咯并喹啉衍生物的高效，经济，环保的合成方法。通过使用水作为反应介质和使用乙酸（AcOH）作为绿色促进剂来制备-3-甲基异恶唑。该方案的优点是环保，无金属，反应时间短，操作简便，产率高，底物范围广且易于纯化。最重要的是，此方法是绿色的。