2-hydroxy-4'-methoxy-α,β-dihydrochalcone | 88214-90-8

• 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: 2-hydroxy-4'-methoxy-α,β-dihydrochalcone
• 英文别名: 3-(2-hydroxyphenyl)-1-(4-methoxyphenyl)propan-1-one；3-(2-hydroxy-phenyl)-1-(4-methoxy-phenyl)-propan-1-one；3-(2-Hydroxy-phenyl)-1-(4-methoxy-phenyl)-propan-1-on
• CAS: 88214-90-8
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: AFBIFHWAZJFTDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-hydroxy-4'-methoxy-α,β-dihydrochalcone 在 potassium carbonate 、 对甲苯磺酰肼 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到2-(4-methoxy-phenyl)-chroman
  参考文献：
  名称：

  Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans

  摘要：

  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.

  DOI：

  10.1016/j.tet.2015.08.027
• 作为产物：
  描述：

  4'-methoxyflav-2-ene 在 UiO-66-NH₂, o-sulfobenzoic acid derivative 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到2-hydroxy-4'-methoxy-α,β-dihydrochalcone
  参考文献：
  名称：

  Homodimerization of 2H-chromenes catalyzed by Brønsted-acid derived UiO-66 MOFs

  摘要：

  Brønsted酸UiO-66 MOFs被制备用于高效的2H-色酮的同源二聚化，其中涉及串联重排/杂环Diels-Alder反应序列。

  DOI：

  10.1039/c7cy02362f

文献信息

• Rh-Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A-E
  作者：Maddali L. N. Rao、Boddu S. Ramakrishna

  DOI：10.1002/ejoc.201901314

  日期：2019.12.15

  A Rh‐catalyzed decarbonylative addition of salicylaldehydes with vinyl ketones was developed for the synthesis of o‐hydroxydihydrochalcones in good yields. This protocol was applied in the synthesis of taccabulin family of natural products.

  开发了水杨醛与乙烯基酮进行Rh催化的羰基脱羰加成反应，以高收率合成邻羟基二氢查耳酮。该方案被应用于天然产物他卡布林家族的合成。
• Design, Synthesis, and Biological Evaluation of Novel Hybrids Containing Dihydrochalcone as Tyrosinase Inhibitors to Treat Skin Hyperpigmentation
  作者：Songtao Xue、Zhiwei Li、Xiaotong Ze、Xiuyuan Wu、Chen He、Wen Shuai、Maria Marlow、Jian Chen、David Scurr、Zheying Zhu、Jinyi Xu、Shengtao Xu

  DOI：10.1021/acs.jmedchem.3c00012

  日期：——

  deposition may lead to a series of skin disorders. The production of melanin is carried out by melanocytes, in which the enzyme tyrosinase performs a key role. In this work, we identified a series of novel tyrosinase inhibitor hybrids with a dihydrochalcone skeleton and resorcinol structure, which can inhibit tyrosinase activity and reduce the melanin content in the skin. Compound 11c possessed the most

  黑色素沉积过多可能会导致一系列的皮肤病。黑色素的产生是由黑色素细胞进行的，其中酪氨酸酶起着关键作用。在这项工作中，我们鉴定了一系列具有二氢查耳酮骨架和间苯二酚结构的新型酪氨酸酶抑制剂杂化物，它们可以抑制酪氨酸酶活性并减少皮肤中的黑色素含量。化合物11c具有最强的抗酪氨酸酶活性，在纳摩尔浓度范围内显示出 IC 50值，同时具有显着的抗氧化活性和低细胞毒性。此外，在 HPLC 分析和 3D OrbiSIMS 成像可视化支持下的体外渗透测试表明11c具有出色的渗透性. 更重要的是，化合物11c在体内的豚鼠模型中减少了紫外线诱导的皮肤色素沉着中的黑色素含量。这些结果表明，化合物11c可以作为一种很有前途的强效酪氨酸酶抑制剂，用于开发治疗皮肤色素沉着过度的潜在疗法。
• Brønsted Acid Catalyzed Intramolecular Allylic Substitution Reaction of Allylic Alcohols: A Facile Synthesis of 2-Vinylchromans
  作者：Chang-Hua Ding、Bin Xu、Yun-Fan Li、Yu-Ting Xi、Kai-Ji Hu、Qitao Tan

  DOI：10.1055/a-2301-9223

  日期：——

  Brønsted acid catalyzed intramolecular allylic substitution reaction of secondary and tertiary allylic alcohols has been developed. A variety of 2-vinylchromans were efficiently prepared in moderate to excellent yields. The given method features wide substrate scope, operational simplicity, and mild, metal-free reaction conditions. The practicability of the method was demonstrated by a gram-scale reaction

  已开发出布朗斯台德酸催化仲烯丙醇和叔烯丙醇的分子内烯丙取代反应。多种 2-乙烯基苯并二氢吡喃以中等至优异的产率有效制备。该方法具有底物范围广、操作简单、反应条件温和、无金属等特点。通过克级反应和产物的进一步衍生证明了该方法的实用性。还对催化不对称反应进行了初步研究。
• Iron-Catalyzed Rearrangements and Cycloaddition Reactions of 2<i>H</i>-Chromenes
  作者：Yi Luan、Huan Sun、Scott E. Schaus

  DOI：10.1021/ol202772k

  日期：2011.12.16

  Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway.
• Bird, T. Geoffrey C.; Brown, Ben R.; Stuart, Ian A., Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1831 - 1846
  作者：Bird, T. Geoffrey C.、Brown, Ben R.、Stuart, Ian A.、Tyrrell, William R.

  DOI：——

  日期：——