1,3-bis(2-hydroxyphenyl)propan-1-one | 29337-78-8

• 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: 1,3-bis(2-hydroxyphenyl)propan-1-one
• 英文别名: 1,3-Bis-o-hydroxyphenyl-prop-1-on；1,3-Bis(2-hydroxyphenyl)propan-1-one
• CAS: 29337-78-8
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: IWADQUTZKMPBRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis(2-hydroxyphenyl)propan-1-one 、 乙二胺 在 乙醇 作用下， 生成 N,N'-bis-[1,3-bis-(2-hydroxy-phenyl)-propyliden]-ethylenediamine
  参考文献：
  名称：

  Tsumaki et al., Nippon Kagaku Zasshi, 1951, vol. 72, p. 368

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-2,2'-dihydroxychalcone 在 钯 、 溶剂黄146 作用下， 生成 1,3-bis(2-hydroxyphenyl)propan-1-one
  参考文献：
  名称：

  Tsumaki et al., Nippon Kagaku Zasshi, 1951, vol. 72, p. 368

  摘要：

  DOI：

文献信息

• Metal‐free Synthesis of Spiro‐2,2′‐benzo[ <i>b</i> ]furan‐3,3′‐ones <i>via</i> PhI(OAc) ₂ ‐Mediated Cascade Spirocyclization
  作者：Qingyu Xing、Huiyuan Liang、Mingmai Bao、Xuemin Li、Jingran Zhang、Tianhao Bi、Yilin Zhang、Jun Xu、Yunfei Du、Kang Zhao

  DOI：10.1002/adsc.201900652

  日期：2019.10.22

  Treating the benzyl protected 3‐hydroxy‐1,3‐bis(2‐hydroxyphenyl)prop‐2‐en‐1‐ones solely with PhI(OAc)2 (PIDA) in DCE at room temperature readily furnished the seldom studied spiro‐2,2′‐benzo[b]furan‐3,3′‐ones in satisfactory to excellent yields. The hypervalent iodine reagent enables the metal‐free cascade spirocyclization resulting in the dual oxidative C−O bond formation.

  在室温下仅用PhI（OAc）2（PIDA）在室温下仅用PhI（OAc）2（PIDA）处理苄基保护的3-羟基-1,3-双（2-羟基苯基）丙-2-烯-1-酮很容易提供很少研究的spiro-2 ，2'-苯并[b]呋喃-3,3'-酮类产品具有令人满意的优异收率。高价碘试剂可实现无金属级联螺环化，从而形成双氧化C-O键。
• Effect of OH substitution in 3-benzylchroman-4-ones: crystallographic, CSD, DFT, FTIR, Hirshfeld surface, and energy framework analysis
  作者：Abdul Ajees Abdul Salam、Shilpa T.、Madan Kumar S.、Aseefhali Bankapur、Rajeev K. Sinha、Lalitha Simon、Santhosh Chidangil

  DOI：10.1039/d1ra02245h

  日期：——

  4-dihydro-2H-1-benzopyran-4-one. The single crystals were grown using a novel laser-induced crystallization technique. We observed that the 3-benzylchroman-4-one derivative bearing OH substitution at the 2′ position adopted different conformation due to formation of dimers through O–H⋯O, and C–H⋯O intermolecular hydrogen bondings. The role of OH substitution in the aforementioned conformational changes was evaluated

  3-Benzylchroman-4-ones（高异黄烷酮）是具有十六碳骨架的含氧杂环。它们属于天然存在的多酚类黄酮类化合物，在自然界中存在有限，具有抗炎、抗菌、抗组胺、抗诱变、抗病毒和血管保护特性。最近，我们报道了15个3-benzylchroman-4-one分子的合成和抗癌活性研究，其中大部分被证明对BT549和HeLa细胞有效。在这项工作中，我们报告了两个分子 3-[(2-羟基苯基)甲基]-3,4-dihydro-2 H -1-benzopyran-4-one 和 3-[( 2,4-二甲氧基苯基)甲基]-3,4-二氢-2 H-1-苯并吡喃-4-一。使用新型激光诱导结晶技术生长单晶。我们观察到在 2' 位带有 OH 取代的 3-benzylchroman-4-one 衍生物由于通过 O-H⋯O 和 C-H⋯O 分子间氢键形成二聚体而采用不同的构象。使用密度泛函理论 (DFT)、Hirshfeld
• Palladium-Catalyzed Multicomponent Cascade Reaction of 3-Hydroxypropionitrile: Synthesis of Substituted Dihydrochalcones
  作者：Jinming Zheng、Qingzong Wang、Yifei Li、Huixian Zheng、Chaoyi Hu、Xiaodong Hu、Xiaoxia Ye、Jiuxi Chen、Renhao Li

  DOI：10.1021/acs.joc.3c00769

  日期：2023.7.7

  Direct access to substituted dihydrochalcones from the easily available starting materials 3-hydroxypropionitrile derivatives and arylboronic acids is described. The procedure involves a multicomponent aryl addition/hydroxyl elimination/reduction Heck approach in the presence of a Pd catalyst with excellent functional group tolerance and a wide range of substrates. In addition, mixed 1,3-diarylation

  描述了从容易获得的起始原料3-羟基丙腈衍生物和芳基硼​​酸直接获得取代的二氢查尔酮。该过程涉及在具有优异官能团耐受性和多种底物的 Pd 催化剂存在下采用多组分芳基加成/羟基消除/还原 Heck 方法。此外，还实现了使用两种具有不同电子性质的芳基硼酸对3-羟基丙腈进行混合1,3-二芳基化。
• An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
  作者：Gourhari Maiti、Utpal Kayal、Rajiv Karmakar、Rudraksha N. Bhattacharya

  DOI：10.1016/j.tetlet.2012.08.117

  日期：2012.11

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.
• Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans
  作者：Xuyang Shang、Xiaomeng Zhou、Wei Zhang、Changfeng Wan、Junmin Chen

  DOI：10.1016/j.tet.2015.08.027

  日期：2015.10

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.