[7-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-5-yl] acetate | 1082704-39-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: [7-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-5-yl] acetate
• 英文别名: [7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-5-yl] acetate
• CAS: 1082704-39-9
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: YCYGKICWVQYBEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(4-乙酰氧基苯基)-4-氧代-3,4-二氢-2H-苯并吡喃-5,7-二基二乙酸酯 在 Candida antarctica lipase B 、 环戊醇 作用下， 反应 24.0h， 生成 [7-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-5-yl] acetate 、 (±)-5,7-diacetoxy-4'-hydroxyflavan-4-one
  参考文献：
  名称：

  Chemo-enzymatic transformation of naturally abundant naringin to luteolin, a flavonoid with various biological effects

  摘要：

  Luteolin [3',4',5,7-tetrahydroxyflavone], having multiple biological effects such as anti-inflammation, anti-allergy and anti-cancer, was prepared by chemo-enzymatic synthesis from naringin, a naturally abundant flavonoid glycoside. On the occasion of Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on peracetylated form of naringin, an acetate on C-4' was exclusively deprotected to give the key intermediate. The oxidation with 2-iodoxybenzoic acid (IBX) followed by the reductive workup provided regioselectively C-3'and C-4' catechol functionality. After protection of the above-mentioned diol with methoxymethyl (MOM) groups and subsequent hydrolysis of all acetyl groups, a dehydrogenative introduction of double bond between C-2 and C-3 was done by the treatment with I-2. Acid-catalyzed simultaneous removal of MOM groups and glycoside provided luteolin in total 8 steps and 36% overall yield from the starting material. Throughout the synthesis, diglycoside side chain effectively worked as the protective group on C-7 hydroxy group. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.03.002

文献信息

• Chemo-enzymatic transformation of naturally abundant naringin to luteolin, a flavonoid with various biological effects
  作者：Ryohei Kobayashi、Takasi Itou、Kengo Hanaya、Mitsuru Shoji、Noriyasu Hada、Takeshi Sugai

  DOI：10.1016/j.molcatb.2013.03.002

  日期：2013.8

  Luteolin [3',4',5,7-tetrahydroxyflavone], having multiple biological effects such as anti-inflammation, anti-allergy and anti-cancer, was prepared by chemo-enzymatic synthesis from naringin, a naturally abundant flavonoid glycoside. On the occasion of Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on peracetylated form of naringin, an acetate on C-4' was exclusively deprotected to give the key intermediate. The oxidation with 2-iodoxybenzoic acid (IBX) followed by the reductive workup provided regioselectively C-3'and C-4' catechol functionality. After protection of the above-mentioned diol with methoxymethyl (MOM) groups and subsequent hydrolysis of all acetyl groups, a dehydrogenative introduction of double bond between C-2 and C-3 was done by the treatment with I-2. Acid-catalyzed simultaneous removal of MOM groups and glycoside provided luteolin in total 8 steps and 36% overall yield from the starting material. Throughout the synthesis, diglycoside side chain effectively worked as the protective group on C-7 hydroxy group. (C) 2013 Elsevier B.V. All rights reserved.