cis-1,3-bis[3,4-di-O-(methoxycarbonyl)caffeoyloxy]cyclohexane | 861897-15-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cis-1,3-bis[3,4-di-O-(methoxycarbonyl)caffeoyloxy]cyclohexane
• 英文别名: [(1R,3S)-3-[(E)-3-[3,4-bis(methoxycarbonyloxy)phenyl]prop-2-enoyl]oxycyclohexyl] (E)-3-[3,4-bis(methoxycarbonyloxy)phenyl]prop-2-enoate
• CAS: 861897-15-6
• 化学式: C₃₂H₃₂O₁₆
• 分子量: 672.596
• InChiKey: XDFIFTSBKNOQKV-NUIOUTBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  48
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  cis-1,3-bis[3,4-di-O-(methoxycarbonyl)caffeoyloxy]cyclohexane 在 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 cis-1,3-dicaffeoyloxycyclohexane
  参考文献：
  名称：

  Radical scavenging activity of dicaffeoyloxycyclohexanes: Contribution of an intramolecular interaction of two caffeoyl residues

  摘要：

  Six regio- and stereoisomers of dicaffeoyloxycyclohexanes and 2,4-di-O-caffeoyl-1,6-anhydro-beta-D-glucose were synthesized as model compounds of dicaffeoylquinic acids, and their radical scavenging activity was evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) diammonium salt) radical scavenging tests. Both DPPH and ABTS radical scavenging reactions of these compounds consisted of two different steps. In the first step, catechol moieties of the caffeoyl residues were rapidly converted to o-quinone structures and no significant difference in the reactivity was observed among the tested compounds. In the second step, however, the rate of the reaction increased as the intramolecular distance of the two caffeoyl residues decreased. A novel intramolecular coupling product, which could scavenge additional radicals, was isolated from the reaction mixture of trans-1,2-dicaffeoyloxycyclohexane and DPPH radical. The result suggests that the second step of the radical scavenging reaction is arising from an intramolecular interaction between the two caffeoquinone residues to regenerate catechol structures, and that the closer their distance is, the more rapidly they react. The radical scavenging activity of natural dicaffeoylquinic acids in a biological aqueous system might also depend on the positions of caffeoyl ester groups. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.049
• 作为产物：
  描述：

  TRANS-咖啡酸 在 sodium hydroxide 、 草酰氯 作用下， 以 甲苯 为溶剂， 反应 2.83h， 生成 cis-1,3-bis[3,4-di-O-(methoxycarbonyl)caffeoyloxy]cyclohexane
  参考文献：
  名称：

  Radical scavenging activity of dicaffeoyloxycyclohexanes: Contribution of an intramolecular interaction of two caffeoyl residues

  摘要：

  Six regio- and stereoisomers of dicaffeoyloxycyclohexanes and 2,4-di-O-caffeoyl-1,6-anhydro-beta-D-glucose were synthesized as model compounds of dicaffeoylquinic acids, and their radical scavenging activity was evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) diammonium salt) radical scavenging tests. Both DPPH and ABTS radical scavenging reactions of these compounds consisted of two different steps. In the first step, catechol moieties of the caffeoyl residues were rapidly converted to o-quinone structures and no significant difference in the reactivity was observed among the tested compounds. In the second step, however, the rate of the reaction increased as the intramolecular distance of the two caffeoyl residues decreased. A novel intramolecular coupling product, which could scavenge additional radicals, was isolated from the reaction mixture of trans-1,2-dicaffeoyloxycyclohexane and DPPH radical. The result suggests that the second step of the radical scavenging reaction is arising from an intramolecular interaction between the two caffeoquinone residues to regenerate catechol structures, and that the closer their distance is, the more rapidly they react. The radical scavenging activity of natural dicaffeoylquinic acids in a biological aqueous system might also depend on the positions of caffeoyl ester groups. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.049

文献信息

• Radical scavenging activity of dicaffeoyloxycyclohexanes: Contribution of an intramolecular interaction of two caffeoyl residues
  作者：Shizuka Saito、Satoshi Kurakane、Miyuki Seki、Eiji Takai、Takanori Kasai、Jun Kawabata

  DOI：10.1016/j.bmc.2005.04.049

  日期：2005.7

  Six regio- and stereoisomers of dicaffeoyloxycyclohexanes and 2,4-di-O-caffeoyl-1,6-anhydro-beta-D-glucose were synthesized as model compounds of dicaffeoylquinic acids, and their radical scavenging activity was evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) diammonium salt) radical scavenging tests. Both DPPH and ABTS radical scavenging reactions of these compounds consisted of two different steps. In the first step, catechol moieties of the caffeoyl residues were rapidly converted to o-quinone structures and no significant difference in the reactivity was observed among the tested compounds. In the second step, however, the rate of the reaction increased as the intramolecular distance of the two caffeoyl residues decreased. A novel intramolecular coupling product, which could scavenge additional radicals, was isolated from the reaction mixture of trans-1,2-dicaffeoyloxycyclohexane and DPPH radical. The result suggests that the second step of the radical scavenging reaction is arising from an intramolecular interaction between the two caffeoquinone residues to regenerate catechol structures, and that the closer their distance is, the more rapidly they react. The radical scavenging activity of natural dicaffeoylquinic acids in a biological aqueous system might also depend on the positions of caffeoyl ester groups. (c) 2005 Elsevier Ltd. All rights reserved.