3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)-1-propanone | 126380-10-7

• 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: 3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)-1-propanone
• 英文别名: 2',3',4',6'-tetrahydroxydihydrochalcone；1-Propanone, 3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)-；3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)propan-1-one
• CAS: 126380-10-7
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: INIJLHIRVSDRAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 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：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)-1-propanone 以72%的产率得到
  参考文献：
  名称：

  Sato Shingo, Obara Heitaro, Takeuchi Hiroto, Tawaraya Takashi, Endo Akira+, Phitochemistry, 38 (1995) N 2, S 491-493

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,5-tetrahydroxybenzene 、 苯代丙腈 在 盐酸 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以63%的产率得到3-phenyl-1-(2,3,4,6-tetrahydroxyphenyl)-1-propanone
  参考文献：
  名称：

  Ceratiolin 的合成，Ceratiola ericoides 的一种成分

  摘要：

  Ceratiolin 是 Ceratiola ericoides 的一种成分，通过 2',3',4',6'-四羟基二氢查耳酮的甲基化合成，由 1,2,3,5-苯四醇与 3-苯基丙腈的 Hoesch 反应制备。此外，已证明通过 2',4',6'-三羟基-3',5'-二甲基二氢查尔酮的氧化很容易形成 ceratiolin。

  DOI：

  10.1246/bcsj.62.3371

文献信息

• Synthesis of Ceratiolin, a Constituent of<i>Ceratiola ericoides</i>
  作者：Heitaro Obara、Jun-ichi Onodera、Katsuhiro Yusa、Mitsuhiro Tsuchiya、Shigeru Matsuba

  DOI：10.1246/bcsj.62.3371

  日期：1989.10

  Ceratiolin, a constituent of Ceratiola ericoides was synthesized by the methylation of 2′,3′,4′,6′-tetrahydroxydihydrochalcone, prepared by the Hoesch reaction of 1,2,3,5-benzenetetrol with 3-phenylpropionitrile. Furthermore, it was proved that ceratiolin easily forms by the oxidation of 2′,4′,6′-trihydroxy-3′,5′-dimethyldihydrochalcone.

  Ceratiolin 是 Ceratiola ericoides 的一种成分，通过 2',3',4',6'-四羟基二氢查耳酮的甲基化合成，由 1,2,3,5-苯四醇与 3-苯基丙腈的 Hoesch 反应制备。此外，已证明通过 2',4',6'-三羟基-3',5'-二甲基二氢查尔酮的氧化很容易形成 ceratiolin。
• α-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as α-glucosidase inhibitors
  作者：Hong Gao、Jun Kawabata

  DOI：10.1016/j.bmc.2004.12.010

  日期：2005.3.1

  The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyi-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively/ (C) 2004 Elsevier Ltd. All rights reserved.
• OBARA, HEITARO;ONODERA, JUN-ICHI;YUSA, KATSUHIRO;TSUCHIYA, MITSUHIRO;MATS+, BULL. CHEM. SOC. JAP., 62,(1989) N0, C. 3371-3372
  作者：OBARA, HEITARO、ONODERA, JUN-ICHI、YUSA, KATSUHIRO、TSUCHIYA, MITSUHIRO、MATS+

  DOI：——

  日期：——
• Sato Shingo, Obara Heitaro, Takeuchi Hiroto, Tawaraya Takashi, Endo Akira+, Phitochemistry, 38 (1995) N 2, S 491-493
  作者：Sato Shingo, Obara Heitaro, Takeuchi Hiroto, Tawaraya Takashi, Endo Akira+

  DOI：——

  日期：——
• Syntheses of 2,4,6-trihydroxy-, 2,4,6-trihydroxy-5-methyl- and 2,4,5,6-tetrahydroxy-substituted 3-(3-phenylpropionyl)benzaldehydes and their bactericidal activity
  作者：Shingo Sato、Heitaro Obara、Hiroto Takeuchi、Takashi Tawaraya、Akira Endo、Jun-Ichi Onodera

  DOI：10.1016/0031-9422(94)00699-t

  日期：1995.1

  2,4,6-Trihydroxy-, 2,4,6-trihydroxy-5-methyl-, and 2,4,5,6-tetrahydroxy-substituted 3-(3-phenylpropionyl) benzaldehydes were efficiently synthesized. The first two compounds showed bactericidal activity for Pseudoperonospora cubersis.