1-(2-hydroxy-4-methoxy-5-methylphenyl)ethanone | 81511-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxy-4-methoxy-5-methylphenyl)ethanone
• CAS: 81511-52-6
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: SWECHUQYRSDDTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-hydroxy-4-methoxy-5-methylphenyl)ethanone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 氯仿 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-(2-hydroxy-4-methoxy-5-methylphenyl)propan-1-one
  参考文献：
  名称：

  三种天然1,3-二芳基丙烷的合成：两个修正结构☆

  摘要：

  摘要 1-(2',4'-dihydroxy-3',5'-二甲基苯基)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-Propane，从 Iryanthera coriacea 和 I. laevis 中分离出来，1 -(2'-羟基-4'-甲氧基-5'-甲基苯基)-3-(2"-羟基-4",5"-亚甲基-二氧苯基)-丙烷，从 I. laevis 中分离，和 1-(2 '-羟基-4'-甲氧基苯基)-3-(3″-羟基-4″-甲氧基苯基)-丙烷，从多神经病毒中分离，通过涉及适当查耳酮的催化氢化和二氢查耳酮的克莱门森还原的方法合成。仅修订了从 V. multinervia 和 I. laevis 中分离出来的 1,3-二芳基丙烷的结构。

  DOI：

  10.1016/0031-9422(89)85046-0
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 盐酸 、 水 、 汞 、 zinc(II) chloride 、 锌 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 生成 1-(2-hydroxy-4-methoxy-5-methylphenyl)ethanone
  参考文献：
  名称：

  三种天然1,3-二芳基丙烷的合成：两个修正结构☆

  摘要：

  摘要 1-(2',4'-dihydroxy-3',5'-二甲基苯基)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-Propane，从 Iryanthera coriacea 和 I. laevis 中分离出来，1 -(2'-羟基-4'-甲氧基-5'-甲基苯基)-3-(2"-羟基-4",5"-亚甲基-二氧苯基)-丙烷，从 I. laevis 中分离，和 1-(2 '-羟基-4'-甲氧基苯基)-3-(3″-羟基-4″-甲氧基苯基)-丙烷，从多神经病毒中分离，通过涉及适当查耳酮的催化氢化和二氢查耳酮的克莱门森还原的方法合成。仅修订了从 V. multinervia 和 I. laevis 中分离出来的 1,3-二芳基丙烷的结构。

  DOI：

  10.1016/0031-9422(89)85046-0

文献信息

• Matsuura, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 298,300
  作者：Matsuura

  DOI：——

  日期：——
• Antiproliferative activity of chalcones with basic functionalities
  作者：Xiaoling Liu、Mei-Lin Go

  DOI：10.1016/j.bmc.2007.07.042

  日期：2007.11

  A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar Volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but Still maintained a good activity profile with IC50 < 10 PM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. (C) 2007 Elsevier Ltd. All rights reserved.
• A Facile Baker-Venkataraman Synthesis of Flavones using Phase Transfer Catalysis
  作者：P. K. Jain、J. K. Makrandi、S. K. Grover

  DOI：10.1055/s-1982-29755

  日期：——
• MORAIS, ANSELMO A.;FO, RAIMUNDO BRAZ;FRAIZ, SILVAS V. (JR), PHYTOCHEMISTRY, 28,(1989) N 1, C. 239-242
  作者：MORAIS, ANSELMO A.、FO, RAIMUNDO BRAZ、FRAIZ, SILVAS V. (JR)

  DOI：——

  日期：——
• Synthesis of three natural 1,3-diarylpropanes: Two revised structures
  作者：Anselmo A. Morais、Raimundo Braz Fo、Silas V. Fraiz

  DOI：10.1016/0031-9422(89)85046-0

  日期：——

  5′-dimethylphenyl)-3-(2″-hydroxy-4″,5″-methylenedioxyphenyl)-Propane, isolated from Iryanthera coriacea and I. laevis, 1-(2′-hydroxy-4′-methoxy-5′-methylphenyl)-3-(2″-hydroxy-4″,5″-methylene-dioxyphenyl)-propane, isolated from I. laevis, and 1-(2′-hydroxy-4′-methoxyphenyl)-3-(3″-hydroxy-4″-methoxyphenyl)-propane, isolated from Virola multinervia, were synthesized by processes which involved catalytic hydrogenation

  摘要 1-(2',4'-dihydroxy-3',5'-二甲基苯基)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-Propane，从 Iryanthera coriacea 和 I. laevis 中分离出来，1 -(2'-羟基-4'-甲氧基-5'-甲基苯基)-3-(2"-羟基-4",5"-亚甲基-二氧苯基)-丙烷，从 I. laevis 中分离，和 1-(2 '-羟基-4'-甲氧基苯基)-3-(3″-羟基-4″-甲氧基苯基)-丙烷，从多神经病毒中分离，通过涉及适当查耳酮的催化氢化和二氢查耳酮的克莱门森还原的方法合成。仅修订了从 V. multinervia 和 I. laevis 中分离出来的 1,3-二芳基丙烷的结构。