caffeic acid anhydride tetraacetate | 102876-69-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: caffeic acid anhydride tetraacetate
• 英文别名: 3-(3,4-Diacetyloxyphenyl)prop-2-enoyl 3-(3,4-diacetyloxyphenyl)prop-2-enoate；3-(3,4-diacetyloxyphenyl)prop-2-enoyl 3-(3,4-diacetyloxyphenyl)prop-2-enoate
• CAS: 102876-69-7
• 化学式: C₂₆H₂₂O₁₁
• 分子量: 510.454
• InChiKey: CYDAXQWBLCWHAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  caffeic acid anhydride tetraacetate 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成
  参考文献：
  名称：

  Synthesis of (+)- and (−)-Phaselic Acid

  摘要：

  The syntheses of both enantiomers of phaselic acid (2-O-caffeoylmalate) are described. The previously unreported acetate-protected caffeic acid anhydride was used with appropriately protected malic acid derivatives as coupling partners to provide fully protected phaselic acid. Sequential unmasking of the protecting groups afforded phaselic acid in an acceptable overall yield. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.633252
• 作为产物：
  描述：

  三光气 、 以 乙酸乙酯 为溶剂， 生成 caffeic acid anhydride tetraacetate
  参考文献：
  名称：

  Synthesis of (+)- and (−)-Phaselic Acid

  摘要：

  The syntheses of both enantiomers of phaselic acid (2-O-caffeoylmalate) are described. The previously unreported acetate-protected caffeic acid anhydride was used with appropriately protected malic acid derivatives as coupling partners to provide fully protected phaselic acid. Sequential unmasking of the protecting groups afforded phaselic acid in an acceptable overall yield. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.633252

文献信息

• Synthesis of 1-<i>O</i>-Methylchlorogenic Acid: Reassignment of Structure for MCGA3 Isolated from Bamboo (<i>Phyllostachys edulis</i>) Leaves
  作者：Wayne E. Zeller

  DOI：10.1021/jf4042112

  日期：2014.2.26

  coincide with those reported for the original isolation from bamboo (Phyllostachys edulis) leaves of the compound designated MCGA3. Comparison of the published spectroscopic data reported for MCGA3, with both reported literature values and spectroscopic data obtained from an authentic sample, leads to the conclusion that the compound isolated from bamboo (Phyllostachys edulis) leaves is instead methyl

  描述了1- O-甲基绿原酸的第一次合成。这种化合物的短而有效的合成提供了实验室规模的材料以研究其生物学特性。合成包括将已知的（-）-4,5-环己叉基奎宁内酯进行C-1烷基化，然后将甲醇盐打开至羟基酯。将C-5羟基酰化，随后依次除去保护基，得到1- O-甲基绿原酸。该化合物的NMR光谱特征与最初从竹子（毛竹（Phyllostachys edulis））称为MCGA3的化合物的叶子。将报告的MCGA3光谱数据与已报道的文献数据和从真实样品中获得的光谱数据进行比较，得出的结论是，从竹叶（Phyllostachys edulis）叶中分离出的化合物是氯代甲烷。