4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone

• 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: 4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone
• 英文别名: 1-(4-Methoxyphenyl)-3-[4-(oxan-2-yloxy)phenyl]prop-2-en-1-one；1-(4-methoxyphenyl)-3-[4-(oxan-2-yloxy)phenyl]prop-2-en-1-one
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: BCTCXFYNWBVMCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以90%的产率得到4-hydroxy-4'-methoxychalcone
  参考文献：
  名称：

  使用Sn（IV）Cl 4催化剂对苯酚四氢吡喃基和甲氧基甲基醚进行高效脱保护并续环成茚满酮

  摘要：

  Sn（IV）Cl 4催化剂在温和条件下为酚THP和MOM醚以及THP和MOM保护的查耳酮环氧化物的后续分子内Friedel-Crafts烷基化反应提供了一种快速有效的脱保护方法。反应历时2-3分钟，在0°C时以优异的收率（90–98％）得到了产品，而没有影响其他官能团。

  DOI：

  10.1016/j.tetlet.2014.05.009
• 作为产物：
  描述：

  4-(四氢-吡喃-2-基氧基)-苯甲醛 、 对甲氧基苯乙酮 在 三乙胺 作用下， 生成 4'-methoxy-4-(tetrahydropyran-2-yloxy)chalcone
  参考文献：
  名称：

  Synthesis and Photoinduced Reorientation of Polymethacrylates Comprising Photocrosslinkable Phenylbenzoate Mesogenic Side Groups

  摘要：

  This paper describes synthesis and photoreaction of photocrosslinkable liquid crystalline (LC) polymethacrylates comprising phenyl benzoate mesogenic side groups attached with a photoreactive end group. All synthesized polymers exhibited a nematic LC nature. Irradiating the polymer film with linearly polarized ultraviolet (LPUV) light induced a negative optical anisotropy due to an axis-selective photoreaction of the mesogenic groups. When the exposed film was annealed at the LC temperature range reversion of the reorientation direction was observed, which was triggered by the photocrosslinked mesogenic groups act as "command in bulk".

  DOI：

  10.1080/154214091009671

文献信息

• Synthesis and Photoinduced Reorientation of Polymethacrylates Comprising Photocrosslinkable Phenylbenzoate Mesogenic Side Groups
  作者：Nobuhiro Kawatsuki、Yuki Kitani、Akihiro Oda

  DOI：10.1080/154214091009671

  日期：2005.11.1

  This paper describes synthesis and photoreaction of photocrosslinkable liquid crystalline (LC) polymethacrylates comprising phenyl benzoate mesogenic side groups attached with a photoreactive end group. All synthesized polymers exhibited a nematic LC nature. Irradiating the polymer film with linearly polarized ultraviolet (LPUV) light induced a negative optical anisotropy due to an axis-selective photoreaction of the mesogenic groups. When the exposed film was annealed at the LC temperature range reversion of the reorientation direction was observed, which was triggered by the photocrosslinked mesogenic groups act as "command in bulk".
• NOTCH INHIBITORS FOR USE IN THE TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA
  申请人：UNIVERSITÀ DEGLI STUDI DI ROMA "LA SAPIENZA"

  公开号：US20190337916A1

  公开（公告）日：2019-11-07

  Compounds of formula (I) in the capacity of compounds with anti-tumor activity for the treatment of T-cell acute lymphoblastic leukemia (T-ALL).
• Highly efficient deprotection of phenolic tetrahydropyranyl and methoxymethyl ethers and sequel cyclization to indanones using Sn(IV)Cl4 catalyst
  作者：Naseem Ahmed、Gulab Khushalrao Pathe、B. Venkata Babu

  DOI：10.1016/j.tetlet.2014.05.009

  日期：2014.7

  Sn(IV)Cl4 catalyst provided a rapid and efficient deprotection method for the phenolic THP and MOM ethers and sequel intramolecular Friedel–Crafts alkylation reaction of THP and MOM protected chalcone epoxides under mild conditions. The reaction took 2–3 min to give the products in excellent yield (90–98%) at 0 °C without affecting the other functional groups.

  Sn（IV）Cl 4催化剂在温和条件下为酚THP和MOM醚以及THP和MOM保护的查耳酮环氧化物的后续分子内Friedel-Crafts烷基化反应提供了一种快速有效的脱保护方法。反应历时2-3分钟，在0°C时以优异的收率（90–98％）得到了产品，而没有影响其他官能团。
• Synthesis and topoisomerase II inhibitory and cytotoxic activity of oxiranylmethoxy- and thiiranylmethoxy-chalcone derivatives
  作者：Younghwa Na、Jung-Min Nam

  DOI：10.1016/j.bmcl.2010.11.037

  日期：2011.1

  In order to find potential anticancer drug candidate targeting topoisomerases enzyme, we have designed and synthesized oxiranylmethoxy- and thiiranylmethoxy-retrochalcone derivatives and evaluated their pharmacological activity including topoisomerases inhibitory and cytotoxic activity. Of the compounds prepared compound 25 showed comparable or better cytotoxic activity against cancer cell lines tested. Compound 25 inhibited MCF7 (IC50: 0.49 +/- 0.21 mu M) and HCT15 (IC50: 0.23 +/- 0.02 mu M) carcinoma cell growth more efficiently than references. In the topoisomerases inhibition test, all the compounds were inactive to topoisomerase I but moderate inhibitors to topoisomerase II enzyme. Especially, compound 25 inhibited topoisomerase II activity with comparable extent to etoposide at 100 mu M concentrations. Correlation between cytotoxicity and topoisomerase II inhibitory activity implies that compound 25 can be a possible lead compound for anticancer drug impeding the topoisomerase II function. (C) 2010 Elsevier Ltd. All rights reserved.