5-(2-(3,4-二甲氧基苯基)乙基)-2-甲氧基-苯酚 | 63367-99-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 5-(2-(3,4-二甲氧基苯基)乙基)-2-甲氧基-苯酚
• 英文名称: 5-(3,4-dimethoxyphenethyl)-2-methoxyphenol
• 英文别名: 3,4,4'-Trimethoxy-3'-hydroxydibenzyl；Phenol, 5-(2-(3,4-dimethoxyphenyl)ethyl)-2-methoxy-；5-[2-(3,4-dimethoxyphenyl)ethyl]-2-methoxyphenol
• CAS: 63367-99-7
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: UPOANTHMCQBWOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苄氯 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 乙醚 、 溶剂黄146 、 xylene 为溶剂， 生成 5-(2-(3,4-二甲氧基苯基)乙基)-2-甲氧基-苯酚
  参考文献：
  名称：

  异香豆素及相关化合物的化学结构和甜味。九。

  摘要：

  对β-(3-羟基-4-甲氧基苯基)乙基苯（I）的苯基部分（A部分）进行了结构修饰，试图使结构与甜味之间的关系更加明确。合成了I的24种A部分衍生物，其中化合物（II、IV、V、VI、X、XXII、XXIII和XXVI）显示出甜味，而其他化合物则无味。根据这些数据，讨论了这些化合物的味道与取代基的立体化学障碍效应之间的关系。

  DOI：

  10.1248/cpb.25.706

文献信息

• Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives
  作者：Li Guan、Junting Zhou、Qinghua Lin、Huilin Zhu、Wenyuan Liu、Baolin Liu、Yanbo Zhang、Jie Zhang、Jing Gao、Feng Feng、Wei Qu

  DOI：10.1016/j.bmc.2019.04.027

  日期：2019.6

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.
• Chemical structure and sweet taste of isocoumarin and related compounds. IX.
  作者：MASATOSHI YAMATO、KOICHI SATO、KUNIKO HASHIGAKI、TAKAJI KOYAMA

  DOI：10.1248/cpb.25.706

  日期：——

  Structural modification of the phenyl moiety (A moiety) of β-(3-hydroxy-4-methoxyphenyl) ethylbenzene (I), which constitute an essential part of phyllodulcin molecules, was attempted to make the relationship between structure and sweet taste clearer. Twenty-four derivatives of A moiety of I were synthesized, the compound (II, IV, V, VI, X, XXII, XXIII, and XXVI) revealed sweet taste and the other compounds were tasteless. On the basis of these data, the taste of these compounds were discussed in connection with the stereochemical hindrance effect of substituents.

  对β-(3-羟基-4-甲氧基苯基)乙基苯（I）的苯基部分（A部分）进行了结构修饰，试图使结构与甜味之间的关系更加明确。合成了I的24种A部分衍生物，其中化合物（II、IV、V、VI、X、XXII、XXIII和XXVI）显示出甜味，而其他化合物则无味。根据这些数据，讨论了这些化合物的味道与取代基的立体化学障碍效应之间的关系。