3-(4-fluorophenyl)-1-(2-hydroxyphenyl)propan-1-one | 59223-79-9

• 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-fluorophenyl)-1-(2-hydroxyphenyl)propan-1-one
• CAS: 59223-79-9
• 化学式: C₁₅H₁₃FO₂
• 分子量: 244.265
• InChiKey: MJIFFESFGKNVSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-1-(2-hydroxyphenyl)propan-1-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.25h， 生成 3-(4-Fluorophenyl)-1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]propan-1-one;hydrochloride
  参考文献：
  名称：

  Optimization of Propafenone Analogues as Antimalarial Leads

  摘要：

  Propafenone, a class Ic antiarrythmic drug, inhibits growth of cultured Plasmodium falciparum. While the drug's potency is significant, further development of propafenone as an antimalarial would require divorcing the antimalarial and cardiac activities as well as improving the pharmacokinetic profile of the drug. A small array of propafenone analogues was designed and synthesized to address the cardiac ion channel and PK liabilities. Testing of this array revealed potent inhibitors of the 3D7 (drug sensitive) and K1 (drug resistant) strains of P. falciparum that possessed significantly reduced ion channel effects and improved metabolic stability. Propafenone analogues are unusual among antimalarial leads in that they are more potent against the multidrug resistant K1 strain of P. falciparum compared to the 3D7 strain.

  DOI：

  10.1021/jm2005546
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 palladium 10% on activated carbon 、 甲酸铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 3-(4-fluorophenyl)-1-(2-hydroxyphenyl)propan-1-one
  参考文献：
  名称：

  3-苄基苯并吡喃-4-酮衍生物的合成，抗癌，结构和计算对接研究

  摘要：

  合成了一系列的3-苄基苯并吡喃-4-酮，并通过MTT法筛选了其抗癌活性。针对两种癌细胞系BT549（人类乳腺癌），HeLa（人类宫颈癌）和一种非癌细胞系vero（正常肾脏上皮细胞）对化合物进行了评估。发现3b是对抗BT549细胞（IC 50  = 20.1 µM）最活跃的分子，而3h是对抗HeLa细胞（IC 50  = 20.45 µM）最活跃的分子。3b还显示出对HeLa细胞的中等活性（IC 50  = 42.8 µM）。3h和3i的分子结构通过单晶X射线晶体学技术解决。此外，检查了在肿瘤抑制蛋白p53与先导化合物3h之间的分子对接研究，该化合物对HeLa细胞表现出更好的抗癌活性。

  DOI：

  10.1016/j.bmcl.2017.10.026

文献信息

• Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalcones <i>via</i> palladium(<scp>ii</scp>)-catalyzed oxidative cyclization
  作者：Seung Hwan Son、Yang Yil Cho、Hyung-Seok Yoo、Soo Jin Lee、Young Min Kim、Hyu Jeong Jang、Dong Hwan Kim、Jeong-Won Shin、Nam-Jung Kim

  DOI：10.1039/d1ra01672e

  日期：——

  Divergent and versatile synthetic routes to flavones and flavanones via efficient Pd(II) catalysis are disclosed. These Pd(II) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives, via discriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic

  公开了通过有效的 Pd( II ) 催化合成黄酮和黄烷酮的不同且通用的合成路线。根据氧化剂和添加剂，这些 Pd( II ) 催化剂分别以高度原子经济的方式通过涉及脱氢的区分氧化环化序列，方便地从 2'-羟基二氢查耳酮中提供各种黄酮和黄烷酮作为常见的中间体。
• Rhodium-Phosphoramidite Catalyzed Alkene Hydroacylation: Mechanism and Octaketide Natural Product Synthesis
  作者：Max von Delius、Christine M. Le、Vy M. Dong

  DOI：10.1021/ja305593y

  日期：2012.9.12

  heterogeneous base are key for high catalytic activity and linear regioselectivity. This protocol was applied in the atom- and step-economical synthesis of eight biologically active octaketide natural products, including anticancer drug candidate cytosporone B. Mechanistic studies provide insight on parameters affecting decarbonylation, a side reaction that limits the turnover number for catalytic hydroacylation

  我们描述了一种方法，该方法允许水杨醛衍生物以低至 2 mol% 的催化剂负载量与各种未活化的烯烃偶联。手性亚磷酰胺配体和多相碱的精确化学计量是高催化活性和线性区域选择性的关键。该协议应用于八种生物活性八酮天然产物的原子和步骤经济合成，包括抗癌药物候选细胞孢菌素 B。 机理研究提供了对影响脱羰的参数的见解，这是一种限制催化加氢酰化转换数的副反应。氘标记研究表明，支化氢化物插入是完全可逆的，而线性氢化物插入在很大程度上是不可逆的并且限制了转换。我们建议配体 (R(a),R, R)-SIPHOS-PE 通过降低线性选择性途径中还原消除的障碍，有效抑制脱羰，并有助于限制转换的插入。这些因素共同实现了高反应性和区域选择性。
• Solvent‐Controlled Hydrogenation of 2’‐Hydroxychalcones: A Simple Solution to the Total Synthesis of Bussealins
  作者：Martín Soto、Raquel G. Soengas、Humberto Rodríguez‐Solla

  DOI：10.1002/adsc.202000892

  日期：2020.12.8

  dihydrochalcones were isolated. Switching the reaction solvent to n‐BuOH/H2O (1:1), afforded 1,3‐diarylpropanols from moderate to good yields. The methodology here reported offers a straightforward, simple and cost‐effective method for the preparation of a wide variety of 2’‐hydroxy‐1,3‐diarylpropanes derivatives, and was also applied to the preparation of natural Bussealins C and D.

  本文报道了溶剂控制的2'-羟基查耳酮氢化，以选择性地获得不同的氢化产物。因此，使用EtOH作为溶剂对2'-羟基查耳酮进行氢化，可以以优异的产率提供相应的1,3-二芳基丙烷。相反，当在DCM中进行氢化时，分离出相应的二氢查耳酮。将反应溶剂切换为n- BuOH / H 2 O（1：1），得到1,3-二芳基丙醇，产率从中等到良好。此处报道的方法为制备各种2'-羟基-1,3-二芳基丙烷衍生物提供了一种简单，简单且具有成本效益的方法，并且还应用于天然Bussealins C和D的制备。
• Regioselective and chemoselective biotransformation of 2′-hydroxychalcone derivatives by marine-derived fungi
  作者：Iara Lisboa de Matos、Marcia Nitschke、André Luiz Meleiro Porto

  DOI：10.1080/10242422.2021.1956909

  日期：2023.1.2

  biotransformation of the 2′-hydroxychalcone 1a. The main products obtained were from hydrogenation, hydroxylation, and cyclization reactions. Penicillium raistrickii CBMAI 931 catalyzed the chemoselective reduction of 1a to produce 2′-hydroxydihydrochalcone 2a (72%) in 7 days of incubation in phosphate buffer (pH 7). Aspergillus sydowii CBMAI 935 promoted the hydroxylation of 1a to yield 2′,4-dihydroxy-dihydrochalcone

  摘要 八种真菌菌株（Penicillium raistrickii CBMAI 931、Cladosporium sp. CBMAI 1237、Aspergillus sydowii CBMAI 935、Penicillium oxalicum CBMAI 1996、Penicillium citrinum CBMAI 1186、Mucor racemosus CBMAI 847、Westerdykella sp. CBMAI 1679 和 Asperdykella sp. CBMAI 1679 和Aspergillus biorottransformation9 BMAI） 2'-羟基查尔酮1a。获得的主要产物来自氢化、羟基化和环化反应。雷氏青霉CBMAI 931 催化1a化学选择性还原生成 2'-羟基二氢查尔酮2a (72%) 在磷酸盐缓冲液 (pH 7) 中孵育 7 天。Aspergillus
• Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis
  作者：Sofiya A. Runikhina、Alexey A. Tsygankov、Oleg I. Afanasyev、Denis Chusov

  DOI：10.1016/j.mencom.2023.01.005

  日期：2023.1

  Fluoride additive to [(p-cymene)RuCl2]2, a readily available ruthenium catalyst, allows one to achieve milder conditions for the reductive alkylation of aldehydes with ketones using carbon monoxide as a reducing agent. The procedure is suitable for the broad substrate scope, and a probable explanation for the fluoride role was provided.

  [(对伞花烃) RuCl 2 ] 2的氟化物添加剂，一种现成的钌催化剂，允许人们使用一氧化碳作为还原剂实现醛与酮的还原性烷基化。该程序适用于广泛的底物范围，并提供了对氟化物作用的可能解释。