5'-chloro-2'-hydroxy-4'-methylchalcone | 41011-08-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 5'-chloro-2'-hydroxy-4'-methylchalcone
• 英文别名: 2'-hydroxy-4'-methyl-5'-chlorochalcone；1-(5-Chloro-2-hydroxy-4-methylphenyl)-3-phenylprop-2-en-1-one
• CAS: 41011-08-9
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: LXIAAMCDAHDXEY-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  460.9±45.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5'-chloro-2'-hydroxy-4'-methylchalcone 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 双氧水 、 cesium acetate 、 三苯基膦 、 sodium hydroxide 作用下， 以 2-甲基-2-丁醇 、 乙醇 、 水 为溶剂， 反应 22.0h， 生成 5-chloro-6-methyl-2',3'-diphenyl-3H-spiro[benzofuran-2,1'-inden]-3-one
  参考文献：
  名称：

  钌（II）催化的脱羰环化反应合成螺并苯并呋喃酮

  摘要：

  据报道，炔烃通过六元化合物的C / H / C-C活化而首次脱羰基插入。在配体PPh 3存在下，Ru-催化的3-羟基-2-苯基色酮与炔烃的反应最有效，可提供螺茚二苯并呋喃酮。与以前报道的金属催化的脱羰环化反应不同，在本脱羰环化反应中，环化发生在一氧化碳挤出之前。

  DOI：

  10.1002/anie.201710049
• 作为产物：
  描述：

  4-氯-3-甲基苯酚 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 15.0h， 生成 5'-chloro-2'-hydroxy-4'-methylchalcone
  参考文献：
  名称：

  5-氯-6-甲基黄酮衍生物作为潜在抗癌药物的设计、合成和评价

  摘要：

  合成了一系列新型 5-氯-6-甲基橙酮衍生物 (6a-p)，并通过各种光谱技术进行了表征。合成的化合物进行了抗癌活性测试...

  DOI：

  10.1080/07391102.2023.2183716

文献信息

• Kinetic Resolution and Dynamic Kinetic Resolution of Chromene by Rhodium‐Catalyzed Asymmetric Hydroarylation
  作者：Qingjing Yang、Yanbo Wang、Shihui Luo、Jun (Joelle) Wang

  DOI：10.1002/anie.201900721

  日期：2019.4.8

  A highly efficient kinetic resolution and dynamic kinetic resolution of chromene is reported for the first time and they procced by a rhodium‐catalyzed asymmetric hydroarylation pathway. This new approach offers versatile access to various chiral 2,3‐diaryl‐chromanes containing vicinal stereogenic centers, as well as the recovered chiral flavenes, in high yields with excellent ee values (s factor up

  首次报道了色烯的高效动力学拆分和动态动力学拆分，它们是通过铑催化的不对称氢芳基化途径进行的。这种新方法可以以高收率和优异的ee 值（高达532的s因子）提供多种途径获得包含邻位立体异构中心的各种手性2,3-二芳基-苯并二氢吡喃，以及回收的手性黄酮。特别值得注意的是，该策略可以进一步扩展到建立苯二甲醛缩醛动力学拆分的动态版本，并允许完全接触手性异黄酮和α-芳基氢香豆素。
• Palladium catalyzed annulation of 2-iodobiphenyl with a non-terminal alkene enabled by neighboring group assistance
  作者：Bo-Cheng Tang、Cai He、Xiang-Long Chen、Jin-Tian Ma、Miao Wang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1039/d0cc07133a

  日期：——

  In this work, an efficient palladium catalyzed annulation of 2-iodobiphenyl with a non-terminal alkene was developed. The key factor in this transformation was the formation of a highly reactive oxo-palladacycle intermediate, which was enabled by a neighboring hydroxyl group, and remarkably restrained the β-H elimination process. Mechanistically, control experiments demonstrated that the hydroxyl group

  在这项工作中，开发了一种有效的钯催化2-碘联苯与非末端烯烃的环化反应。该转变的关键因素是形成高反应性的羰基-Paladacycle中间体，该中间体可通过相邻的羟基来实现，并显着抑制了β-H的消除过程。从机理上讲，对照实验证明羟基可以充当阴离子配体，在该反应中是不可替代的。该转化表现出良好的反应性和选择性，并且对于所有探索的底物均未检测到简单的Heck偶联产物。
• Shetgiri; Nayak, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 3, p. 683 - 687
  作者：Shetgiri、Nayak

  DOI：——

  日期：——
• New synthesis of flavanones catalyzed by l-proline
  作者：S. Chandrasekhar、K. Vijeender、K. Venkatram Reddy

  DOI：10.1016/j.tetlet.2005.08.066

  日期：2005.10

  L-Proline is utilized as an efficient organocatalyst for the synthesis of substituted flavanones and chalcones in good yields. The efficiency of the catalyst was proved with a variety of substrates ranging from electron-deficient to electron-rich aryl aldehydes and 2-hydroxyacetophenones. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents
  作者：Rafia Bashir、Syed Ovais、Shafiya Yaseen、Hinna Hamid、M.S. Alam、Mohammad Samim、Surender Singh、Kalim Javed

  DOI：10.1016/j.bmcl.2011.05.061

  日期：2011.7

  Thirteen new 2-pyrazoline derivatives bearing benzenesulfonamide moiety (2a-m) were synthesized by condensing appropriate chalcones with 4-hydrazinonbenzenesulfonamide hydrochloride and tested for anticancer and anti-inflammatory actions. According to the protocol of the National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay compounds 2b, 2c, 2e, 2f and 2g exhibited considerable antitumor activities against the entire tested tumor cell lines and showed effective growth inhibition GI(50) (MG-MID) values of 2.63, 2.57, 6.61, 3.31 and 2.57 mu M, respectively, beside a cyclostatic activity TGI (MG-MID) 9.54, 8.51, 24.0, 19.9 and 8.71 mu M, respectively. Two compounds 2g and 2k showed more potent anti-inflammatory activity than celecoxib at 5 h in carrageenan-induced rat paw edema bioassay. These compounds (2g and 2k) proved to have superior gastrointestinal safety profiles as compared to celecoxib, when tested for their ulcerogenic effects. Compounds 2g and 2k showed no inhibition against the enzymatic activity of bovine COX-2 (in vitro). (C) 2011 Elsevier Ltd. All rights reserved.