1-(2-hydroxyphenyl)-2-(4-methoxyphenyl)ethanone | 79744-47-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2-hydroxyphenyl)-2-(4-methoxyphenyl)ethanone
• 英文别名: 2-Hydroxyphenyl 4-methoxybenzyl ketone
• CAS: 79744-47-1
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: CPNQPJQRJKEERT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-2-(4-methoxyphenyl)ethanone 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 18.0h， 生成 4'-methoxyisoflavanone
  参考文献：
  名称：

  Inhibitors of Acyl CoA:Cholesterol Acyltransferase

  摘要：

  Conformational restriction of previously disclosed acyclic diphenylethyl)diphenylacetamides led to the discovery of several potent inhibitors of acyl CoA:cholesterol acyltransferase (ACAT). cis-[2-(4-Hydroxyphenyl)-1-indanyl]diphenylacetamide (4a) was the mo st potent ACAT inhibitor identified (IC50 = 0.04 mu M in an in vitro rat hepatic microsomal ACAT assay, ED(50) = 0.72 mg/kg/day in cholesterol-fed hamsters).

  DOI：

  10.1021/jm950833d
• 作为产物：
  描述：

  苯基2-(4-甲氧基苯基)乙酸酯 在 aluminum (III) chloride 作用下， 反应 1.0h， 生成 1-(2-hydroxyphenyl)-2-(4-methoxyphenyl)ethanone
  参考文献：
  名称：

  3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators

  摘要：

  Following the recent identification of the naturally occurring 3-ylidene-4,5-dihydrophthalide ligustilide and its oxidation product dehydroligustilide as novel TRPA1 modulators, a series of seventeen 3-ylide-nephthalides was synthesized and tested on TRPA1 and TRPM8 channels. Most of these compounds acted as strong modulators of the two channel types with EC50 and/or IC50 values distinctly lower than those of the reference compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.039

文献信息

• New Procedures for the Preparation of Isoflavones with Unsubstituted Ring A
  作者：Albert Lévai、Péter Sebòk

  DOI：10.1080/00397919208020493

  日期：1992.6

  Abstract Isoflavones with unsubstituted ring A have been synthesized either by the ring closure of 2-hy-droxydeoxybenzoins or by the dehydroxylation of 7-hy-droxyisoflavones. 7-Mercaptoisoflavones have also been prepared.

  摘要 具有未取代环 A 的异黄酮已通过 2-羟基脱氧安息香的闭环或通过 7-羟基异黄酮的脱羟基合成。7-巯基异黄酮也已制备。
• Microwave-Assisted Efficient Synthesis of 2-Hydroxydeoxybenzoins from the Alkali Degradation of Readily Prepared 3-Aryl-4-hydroxycoumarins in Water
  作者：Zhong-Zhen Zhou、Guang-Hua Yan、Wen-Hua Chen、Xue-Mei Yang

  DOI：10.1248/cpb.c13-00604

  日期：——

  This paper describes an operationally simple, green and efficient approach for the synthesis of 2-hydroxydeoxybenzoins bearing diverse substituents from the microwave-assisted alkali degradation of 3-aryl-4-hydroxycoumarins in water. The latter compounds were readily prepared from the intramolecular Claisen condensation reaction of methyl 2-(2-arylacetoxy)benzoates in the presence of Cs2CO3-acetone

  本文描述了一种操作简单，绿色高效的方法，该方法可通过微波辅助的3-芳基-4-羟基香豆素在水中的碱降解来合成带有各种取代基的2-羟基脱氧安息香素。后者的化合物很容易从2-（2-芳基乙酰氧基）苯甲酸甲酯的分子内克莱森缩合反应中，在Cs2CO3-丙酮存在下，以极好的收率和费力的后处理步骤制备。该方法是高度原子经济的，因此可用于大规模合成2-羟基脱氧苯偶姻。
• Investigation of the electronic effect of 2-phenylbenzofuran-3-ol derivatives on the protein conformation-induced aggregation
  作者：Saad Alkahtani、Shahnaz Begum、Forid Saikh、Norah S. AL-Johani、Saud Alarifi、Nayim Sepay

  DOI：10.1016/j.molliq.2023.123586

  日期：2024.1

  Gradual deterioration of nerve structures essential for brain functions can occur due to neurodegenerative diseases. Many natural and synthetic compounds can boost or diminish this disease depending upon the structure and electronic features of the compound. We have synthesized three benzofuran molecules having neutral, electron-rich, and electron-deficient natures. They are allowed to interact with

  由于神经退行性疾病，大脑功能所必需的神经结构可能会逐渐退化。许多天然和合成化合物可以增强或减轻这种疾病，具体取决于化合物的结构和电子特征。我们合成了三种具有中性、富电子和缺电子性质的苯并呋喃分子。它们可以与富含 β-折叠的模型蛋白 β-乳球蛋白 (β-lg) 相互作用。它们能够通过疏水相互作用与蛋白质产生强烈的相互作用。化合物的这种相互作用将β-折叠结构改变为β-转角和α-螺旋。蛋白质的这种构象转变影响了蛋白质表面疏水性的增加（通过 ANS 测定证实），这使得蛋白质能够与具有相似结构的另一种蛋白质相互作用。因此，苯并呋喃分子影响蛋白质聚集过程，这一点通过 Th T 测定和 AFM 研究进行了鉴定。在这个过程中，富电子分子比缺电子分子效率更高。因此，富电子苯并呋喃分子可以通过改变其构象来增加蛋白质表面疏水性，从而增加蛋白质聚集。
• Synthesis and post-coital contraceptive activity of a new series of substituted 2,3-diaryl-2H-1-benzopyrans
  作者：K Hajela、RS Kapil

  DOI：10.1016/s0223-5234(97)87540-x

  日期：1997.1

  A series of substituted 2,3-diaryl-2H-1-benzopyrans have been synthesized and screened for their post-coital contraceptive activity in rats. Most of the compounds showed 100% inhibition in a single day schedule at a dose level of 1.0 mg/kg. Compound 32 was found to be the most active with a minimum effective dose (MED) of 0.2 mg/kg in single day testing. Further, it also showed high antiestrogenic activity and is devoid of any agonistic activity.
• Structure-activity relationship of antiestrogens. Phenolic analogs of 2,3-diaryl-2H-1-benzopyrans
  作者：Arun P. Sharma、Ashraf Saeed、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00174a020

  日期：1990.12

  Phenolic analogues of 2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran (1), a novel antiestrogen, were synthesized and evaluated for their structure-activity relationship. Incorporation of OH at position 7 was found to improve receptor affinity of the benzopyran while having no effect on its action as an antagonist. Similar substitution of 2-phenyl as well potentiated receptor affinity as well as antagonist activity of the prototype. The monophenol 19 and the diphenol 25 were thus found to be good receptor ligands, devoid of estrogen agonist activity and associated with marked antiestrogenic activity of comparable order. Both caused nearly complete inhibition of the estradiol stimulated uterine growth in rats as well as mice and were thus found to be better antiestrogens than tamoxifen, trioxifen, and LY-117018. A binding-site model for estrogen receptor rationalizing the structure-activity relationship of benzopyrans in relation to that of the triarylethylene and the triarylpropenone antiestrogens has been discussed.