(1S)-1,5-脱水-1-{2-[4-(beta-D-吡喃葡萄糖基氧基)苯基]-5-羟基-7-甲氧基-4-氧代-4H-苯并吡喃-6-基}-D-山梨糖醇 | 16049-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: (1S)-1,5-脱水-1-{2-[4-(beta-D-吡喃葡萄糖基氧基)苯基]-5-羟基-7-甲氧基-4-氧代-4H-苯并吡喃-6-基}-D-山梨糖醇
• 中文别名: 鸭跖黄酮苷
• 英文名称: Flavocommelin
• 英文别名: 5-hydroxy-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 16049-42-6
• 化学式: C₂₈H₃₂O₁₅
• 分子量: 608.553
• InChiKey: QLOUGKRWTZAXFE-JFECCKQBSA-N

物化性质

• 熔点：
  216-217 °C
• 沸点：
  892.3±65.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (1S)-1,5-脱水-1-{2-[4-(beta-D-吡喃葡萄糖基氧基)苯基]-5-羟基-7-甲氧基-4-氧代-4H-苯并吡喃-6-基}-D-山梨糖醇 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以38%的产率得到当药黄素
  参考文献：
  名称：

  Swertisin dihydrate

  摘要：

  The title compound, 6- C- glucopyranosyl- 7- O- methylapigenin dihydrate, C22H22O10 . 2H(2)O, is a natural C- glucosylflavone. The flavone skeleton is almost planar, the dihedral angle between the pyran moiety and the 4- hydroxyphenyl ring being 9.8 ( 3)degrees. The basal plane of the pyranosyl ring of the glucose moiety is almost perpendicular to the benzopyran ring system. The flavone skeletons are stacked along the a axis, forming layers parallel to ( 001). Between these hydrophobic layers, the glucose groups and water molecules of crystallization are connected via O - H ... O hydrogen bonds, forming hydrophilic layers.

  DOI：

  10.1107/s0108270104028355
• 作为产物：
  描述：

  2,3,4,6-四-O-苯基-Alpha-D-吡喃葡萄糖基三氯乙酰亚氨酸 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 sodium methoxide 、 氢气 、 碘 、 silver carbonate 、 四甲基胍 作用下， 以 1,4-二氧六环 、 喹啉 、 甲醇 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 乙腈 为溶剂， 反应 13.5h， 生成 (1S)-1,5-脱水-1-{2-[4-(beta-D-吡喃葡萄糖基氧基)苯基]-5-羟基-7-甲氧基-4-氧代-4H-苯并吡喃-6-基}-D-山梨糖醇
  参考文献：
  名称：

  Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis

  摘要：

  Flavocommelin, 7-O-methylapigenin 6-C-, 4 '-O-bis-beta-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio-and stereoselective O-glycosylation for an overall yield of 31%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.016

文献信息

• Total Synthesis of Flavocommelin, a Component of the Blue Supramolecular Pigment from <i>Commelina </i><i>c</i><i>ommunis</i>, on the Basis of Direct 6-<i>C</i>-Glycosylation of Flavan
  作者：Kin-ichi Oyama、Tadao Kondo

  DOI：10.1021/jo0494681

  日期：2004.8.1

  We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 Å in CH2Cl2 and a catalytic amount of BF3·Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4‘-O-glycosylation

  我们成功地鸭跖黄酮苷（第一全合成1），蓝色颜料超分子的组分，commelinin（2）中，从鸭跖草，通过直接6- Ç黄烷的-glycosylation 4个使用perbenzylglucosyl氟化物8在MS的存在5.一种在CH 2氯2和BF催化量3 ·的Et 2 O.后6- ç的-glycosylation 4，与CAN氧化成黄烷酮18和随后的4'- ö -glycosylation，与BF的组合促进了3 ·Et 2O和DTBMP，得到二葡糖基黄烷酮20。DDQ氧化20和脱保护依次得到1。
• Flavocommelin octaacetate
  作者：Y. Ohsawa、S. Ohba、S. Kosemura、S. Yamamura、A. Nakagawa、K. Yoshida、T. Kondo

  DOI：10.1107/s0108270193009631

  日期：1994.4.15

  Flavocommelin, 6-beta-D-glucopyranosyl-2-[4-(beta-D-glu-copyranosyloxy)phenyl]-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one, is a flavonoid component of a blue pigment, commelin, which is isolated from the petals of Commelina communis. The crystal structure of the octaacetate derivative, 5-hydroxy-7-methoxy-6-(3,4,5,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2-[4-(3,4,5,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-phenyl]-4H-1-benzopyran-4-one, C44H48O23, has been determined by X-ray diffraction. In the crystal, the molecules are arranged parallel to each other according to the periodicity of the crystal lattice. However, intermolecular stacking of the flavanone skeletons is not observed. This suggests that the hydrophilicity of the glucose moieties is one of the important factors governing the self association.
• Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis
  作者：Kazufumi Misawa、Yoshiki Gunji、Shingo Sato

  DOI：10.1016/j.carres.2013.03.016

  日期：2013.6

  Flavocommelin, 7-O-methylapigenin 6-C-, 4 '-O-bis-beta-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio-and stereoselective O-glycosylation for an overall yield of 31%. (C) 2013 Elsevier Ltd. All rights reserved.
• Swertisin dihydrate
  作者：Shigeru Ohba、Kumi Yoshida、Tadao Kondo

  DOI：10.1107/s0108270104028355

  日期：2004.12.15

  The title compound, 6- C- glucopyranosyl- 7- O- methylapigenin dihydrate, C22H22O10 . 2H(2)O, is a natural C- glucosylflavone. The flavone skeleton is almost planar, the dihedral angle between the pyran moiety and the 4- hydroxyphenyl ring being 9.8 ( 3)degrees. The basal plane of the pyranosyl ring of the glucose moiety is almost perpendicular to the benzopyran ring system. The flavone skeletons are stacked along the a axis, forming layers parallel to ( 001). Between these hydrophobic layers, the glucose groups and water molecules of crystallization are connected via O - H ... O hydrogen bonds, forming hydrophilic layers.