methyl (2'S,3'S)-3-O,4-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate | 943768-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2'S,3'S)-3-O,4-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate
• CAS: 943768-45-4
• 化学式: C₁₅H₂₆O₈
• 分子量: 334.367
• InChiKey: AWMUXJSNEMSNKL-OUMODKTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (2'S,3'S)-3-O,4-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 在 吡啶 、 盐酸 作用下， 以 乙腈 为溶剂， 生成 5-O-cinnamoyl-1-O-methylquinic acid
  参考文献：
  名称：

  Essential structure of co-pigment for blue sepal-color development of hydrangea

  摘要：

  Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al3+ in an aqueous solution around pH 4.0. To clarify the mechanism of blue sepal-color development of hydrangea, we tried to reproduce the blue color in vitro by mixing 1 with designed synthetic co-pigments in the presence of Al3+ at pH 4.0. We at first succeeded in clarifying the essential functional structure in the co-pigment that could form the stable blue solution. Here, we present the structure of the blue pigment caused by an Al-complex coordinating of I at ortho-dihydroxyl groups of the B-ring, 1-hydroxy, 1-carboxylic acid, and the carbonyl residue in the ester at 5-position of 2 and/or 3. The hydrophobic interaction between the aromatic acyl residue at 5-position and the nucleus of 1 may also contribute to stabilize the complex. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.146
• 作为产物：
  描述：

  methyl (2'S,3'S)-5-O-t-butyldimethylsilyl-1-O-methyl-3-O,4-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以30%的产率得到methyl (2'S,3'S)-3-O,4-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate
  参考文献：
  名称：

  Essential structure of co-pigment for blue sepal-color development of hydrangea

  摘要：

  Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al3+ in an aqueous solution around pH 4.0. To clarify the mechanism of blue sepal-color development of hydrangea, we tried to reproduce the blue color in vitro by mixing 1 with designed synthetic co-pigments in the presence of Al3+ at pH 4.0. We at first succeeded in clarifying the essential functional structure in the co-pigment that could form the stable blue solution. Here, we present the structure of the blue pigment caused by an Al-complex coordinating of I at ortho-dihydroxyl groups of the B-ring, 1-hydroxy, 1-carboxylic acid, and the carbonyl residue in the ester at 5-position of 2 and/or 3. The hydrophobic interaction between the aromatic acyl residue at 5-position and the nucleus of 1 may also contribute to stabilize the complex. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.146

文献信息

• Synthesis of Designed Acylquinic Acid Derivatives Involved in Blue Color Development of Hydrangea and Their Co-pigmentation Effect
  作者：Kumi Yoshida、Yuki Toyama-Kato、Tadao Kondo

  DOI：10.3987/com-06-s(k)6

  日期：——