3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one | 76554-31-9

• 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: 3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: 4-chloro-4',6'-dimethoxy-2'-hydroxychalcone
• CAS: 76554-31-9
• 化学式: C₁₇H₁₅ClO₄
• 分子量: 318.757
• InChiKey: QCTNLFAZPZODLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C
• 沸点：
  526.2±50.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 在 copper(l) iodide 、 碘 、 三溴化硼 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 似梨木双黄酮-7-O-B-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Ochnaflavone 的合成及其对 PGE2 生成的抑制作用

  摘要：

  Ochnaflavone 是一种天然存在的双黄酮类化合物，由通过 COC 键连接的两个芹菜素（5,7,4'-三羟基黄酮）单元组成，首先合成并评估了其对生产的抑制活性。通过改性乌尔曼二芳基醚形成作为关键步骤完成全合成。在不同的反应条件下探索了 4'-卤代黄酮和 3'-羟基-5,7,4'-三甲氧基黄酮的偶联反应。4'-氟-5,7-二甲氧基黄酮 (2c) 和 3'-羟基-5,7,4'-三甲氧基黄酮 (2d) 在 N,N-二甲基乙酰胺中的反应以 58% 的收率得到偶联化合物 3。合成的 ochnaflavone 强烈抑制 LPS 激活的 RAW 264.7 细胞中 PGE2 的产生 ()，这是由于 COX-2 的表达减少。相反，汉黄芩素的抑制机制与茯苓黄酮有些不同，虽然汉黄芩素是一种天然存在的抗炎黄酮类化合物，具有很强的抑制活性，似乎是对COX-2酶的抑制。我们简洁的 ochnaflavone 全

  DOI：

  10.5012/bkcs.2014.35.11.3219
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 29.08h， 生成 3-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin

  摘要：

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.

  DOI：

  10.1055/s-0031-1291153

文献信息

• Attrition-Enhanced Deracemization and Absolute Asymmetric Synthesis of Flavanones from Prochiral Precursors
  作者：Waku Shimizu、Naohiro Uemura、Yasushi Yoshida、Takashi Mino、Yoshio Kasashima、Masami Sakamoto

  DOI：10.1021/acs.cgd.0c00955

  日期：2020.9.2

  Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small

  从溶剂中重结晶后，七个外消旋的5,7-二甲氧基黄酮酮提供了凝聚物晶体。研究了三种方法来实现基于手性团聚体系统动态结晶的不对称转化。第一个是通过减磨增强的去消旋作用使外消旋黄烷酮手性对称性破坏。在碱（1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU））和玻璃珠存在下，外消旋黄烷酮在少量丙醇中的连续悬浮促进了手性对称性的破坏并将黄烷酮转化为晶体具有78％至99％ee的（+）-或（-）-对映体。第二种方法涉及中间体醛醇缩合产物的环化，以产生具有90％ee的旋光性黄烷酮，其中涉及可逆的oxa-Michael加成反应以及减磨作用。
• Efficient and Eco-friendly Syntheses of 1,5-Benzothiazepines and 1,5-Benzodiazepines Catalyzed by [<i>Hmim</i>][NO₃] under Mild Conditions
  作者：Hossein Loghmani-Khouzani、Panteha Tamjidi、Iraj Mohammadpoor-Baltork、Marzieh Yaeghoobi、Noorsaadah Abd. Rahman、Ahmad Reza Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiolah Mirkhani、Mohammad Hossein Habibi、Ayana Kashima、Takayoshi Suzuki

  DOI：10.1002/jhet.1827

  日期：2014.1

  Crystal structures of a new thiazepine and diazepine (seven‐membered rings) have also been determined and compared with thiazine (six‐membered ring). In this method, N‐methylimidazolium nitrate [Hmim][NO3] has been used as a catalyst that acts as an environmental friendly system.

  本文介绍了1,5-苯并噻氮杂类和1,5-苯并二氮杂类衍生物的合成方法和反应机理。在这项研究中，已经用新方法制备了36种噻嗪类和二氮杂品（大多数是新的），并通过分光镜方法对其结构进行了表征。还确定了新的噻氮平和二氮杂（七元环）的晶体结构，并将其与噻嗪（六元环）进行了比较。在此方法中，硝酸N甲基咪唑鎓盐[ Hmim ] [NO 3 ]被用作催化剂，对环境无害。
• 查尔酮衍生物合成方法及治疗COPD等肺部炎症药物中的应用
  申请人：广东省科学院动物研究所

  公开号：CN113773188A

  公开（公告）日：2021-12-10

  本发明公开了查尔酮衍生物合成方法及治疗COPD等肺部炎症药物中的应用。查尔酮衍生物，其化学结构如下式(a)所示，式(a)中，R1基团是4‑氯、4‑苄氧基、3‑甲氧基‑4‑苄氧基或2,3,4,5,6‑五甲基。本发明合成了查尔酮衍生物，实验发现，其可以有效抑制肺部炎症反应。因此可以将其用于抑制肺部炎症反应，具有广阔的用途。
• Structure−Activity Relationship Studies of Chalcone Leading to 3-Hydroxy-4,3′,4′,5′-tetramethoxychalcone and Its Analogues as Potent Nuclear Factor κB Inhibitors and Their Anticancer Activities
  作者：Balasubramanian Srinivasan、Thomas E. Johnson、Rahul Lad、Chengguo Xing

  DOI：10.1021/jm901278z

  日期：2009.11.26

  Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-kappa B) activation. The structures of chalcone-based NF-kappa B inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-kappa B inhibition, to explore the feasibility of developing simple chalcone-based potent NF-kappa B inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-kappa B inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-kappa B inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-kappa B inhibitory activities, suggesting that suppressing NF-kappa B activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.
• Silica supported-double metal cyanides (DMCs): A green and highly efficient catalytic protocol for isomerisation of 2′-hydroxychalcones to flavanones
  作者：Naseem Ahmed、Naveen Kumar Konduru、Praveen、Anand Kumar、Kamaluddin

  DOI：10.1016/j.molcata.2013.03.009

  日期：2013.7

  Four different double metal cyanides (NiHCFe, CrHCFe, MnHCFe and ZnHCFe) were synthesized, followed by adsorbed on silica gel and used as Lewis acid catalyst in the isomerisation of substituted 2'-hydroxychalcones to flavanones under solvent-free (dry) condition. Optimization of the reaction condition, temperature effects, DMC catalysts loading and re-useable catalytic activity were further studied during the reaction. Among these catalysts, NiHCFe at 35 mol% loading gave excellent yield (90%) at 100 degrees C temperature in 1.15 h. Catalyst (NiHCFe) easily recovered and re-used six times without much loss of its catalytic activity which gave 80-85% product yields each time. However, these DMCs were failed to give product in the solution phase even prolonging the reaction time at reflux temperature. Similarly, isomerization of substituted 2'-aminochalcones gave 2-5% yields either in solution phase or under solvent-free condition. (C) 2013 Elsevier B.V. All rights reserved.