5-hydroxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-3',4'-bis(methoxymethoxy)flavone | 1449485-92-0

• 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: 5-hydroxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-3',4'-bis(methoxymethoxy)flavone
• CAS: 1449485-92-0
• 化学式: C₃₁H₃₈O₁₇
• 分子量: 682.633
• InChiKey: PIGWDNQKSIGLKG-OFVQHVOFSA-N

物化性质

• 沸点：
  935.2±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.84
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  245.66
• 氢给体数：
  7.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-3',4'-bis(methoxymethoxy)flavone 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 以11.6 mg的产率得到木犀草素
  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
• 作为产物：
  描述：

  5-hydroxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-3',4'-bis(methoxymethoxy)flavan-4-one 在 吡啶 、 碘 作用下， 反应 20.0h， 以26.0 mg的产率得到5-hydroxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-3',4'-bis(methoxymethoxy)flavone
  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