(±)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin | 1616279-88-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (±)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin
• 英文别名: 3,5,7-Trihydroxy-8-[1-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-2-phenylchromen-4-one；3,5,7-trihydroxy-8-[1-(4-hydroxy-3-methoxyphenyl)prop-2-enyl]-2-phenylchromen-4-one
• CAS: 1616279-88-9
• 化学式: C₂₅H₂₀O₇
• 分子量: 432.43
• InChiKey: JRFVOMWWESIGRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  galangin 在 三氯化硼 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到(±)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin
  参考文献：
  名称：

  Gram-scale synthesis of anti-pancreatic flavonoids (±)-8-[1-(4′-hydroxy-3′-methoxyphenyl)prop-2-en-1-yl]-chrysin and -galangin

  摘要：

  Gram-scale total synthesis of (+/-)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin (1) and -chrysin (2) has been accomplished in eight steps from commercially available phloroglucinol and three steps from commercially available chrysin, respectively, featuring an efficient introduction of C(8) (1-prop-2-en-1-yl)phenyl moiety in the natural products through chemo- and regioselective cinnamylation and regioselective aromatic Claisen rearrangement. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.057

文献信息

• Gram-scale synthesis of anti-pancreatic flavonoids (±)-8-[1-(4′-hydroxy-3′-methoxyphenyl)prop-2-en-1-yl]-chrysin and -galangin
  作者：Hyoungsu Kim、Donghee Lim、Iljin Shin、Dongjoo Lee

  DOI：10.1016/j.tet.2014.05.057

  日期：2014.8

  Gram-scale total synthesis of (+/-)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin (1) and -chrysin (2) has been accomplished in eight steps from commercially available phloroglucinol and three steps from commercially available chrysin, respectively, featuring an efficient introduction of C(8) (1-prop-2-en-1-yl)phenyl moiety in the natural products through chemo- and regioselective cinnamylation and regioselective aromatic Claisen rearrangement. (C) 2014 Elsevier Ltd. All rights reserved.