乙酸二聚松柏酯 | 184046-40-0

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: 乙酸二聚松柏酯
• 英文名称: dehydrodiconiferyl diacetate
• 英文别名: Dimeric coniferyl acetate；[(E)-3-[(2S,3R)-3-(acetyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enyl] acetate
• CAS: 184046-40-0
• 化学式: C₂₄H₂₆O₈
• 分子量: 442.466
• InChiKey: TYXVTGSQLKCKCF-FDTLDTTQSA-N

物化性质

• 沸点：
  580.0±50.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸二聚松柏酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以1.8 mg的产率得到(+)-去氢二松柏醇
  参考文献：
  名称：

  Chemical Constituents of Brazilian Propolis and Their Cytotoxic Activities

  摘要：

  The EtOAc-soluble fraction of the MeOH extract of propolis afforded a new prenylated chromane derivative, 3-hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid (1), along with 22 known compounds, 2-23. Of the known compounds, 4, 7, 12-19, and 22 were isolated for the first time from propolis, and the absolute configuration of 23 was established as (2S,3R). Investigation suggested that Baccharis spp. are a significant source of tropical Brazilian propolis, in addition to Clusia minor, Clusia major, and Araucaria heterophylla. All the compounds were tested for their cytotoxicity toward human HT-1080 fibrosarcoma and murine colon 26-L5 carcinoma cells. Among these compounds, 9 and 19-21 showed potent cytotoxicity, having ED50 values equal to or less than 10 mu g/mL.

  DOI：

  10.1021/np980028c
• 作为产物：
  描述：

  阿魏酸甲酯 在 silver(l) oxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 Acetic acid (2R,3R)-5-((E)-3-acetoxy-propenyl)-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-2,3-dihydro-benzofuran-3-ylmethyl ester 、 乙酸二聚松柏酯
  参考文献：
  名称：

  Boehmenan天然产物家族的新木脂素核心的一般方法

  摘要：

  摘要已经实现了一种新的方法来制备波美南天然产物的新木脂素核心骨架和基于Fe（III）促进的氧化偶合的去氢二松香酚醇葡糖苷。将获得的常见中间体进一步选择性修饰，以产生具有三个正交保护的烷氧基官能团的碱性分子核，可用于进一步的选择性修饰。 图形概要

  DOI：

  10.1007/s00706-017-2132-4

文献信息

• Chemical Constituents of Brazilian Propolis and Their Cytotoxic Activities
  作者：Arjun H. Banskota、Yasuhiro Tezuka、Jeevan K. Prasain、Katsumichi Matsushige、Ikuo Saiki、Shigetoshi Kadota

  DOI：10.1021/np980028c

  日期：1998.7.1

  The EtOAc-soluble fraction of the MeOH extract of propolis afforded a new prenylated chromane derivative, 3-hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid (1), along with 22 known compounds, 2-23. Of the known compounds, 4, 7, 12-19, and 22 were isolated for the first time from propolis, and the absolute configuration of 23 was established as (2S,3R). Investigation suggested that Baccharis spp. are a significant source of tropical Brazilian propolis, in addition to Clusia minor, Clusia major, and Araucaria heterophylla. All the compounds were tested for their cytotoxicity toward human HT-1080 fibrosarcoma and murine colon 26-L5 carcinoma cells. Among these compounds, 9 and 19-21 showed potent cytotoxicity, having ED50 values equal to or less than 10 mu g/mL.
• General approach to neolignan-core of the boehmenan natural product family
  作者：Zuzana Barbuščáková、Hana Kozubíková、František Zálešák、Karel Doležal、Jiří Pospíšil

  DOI：10.1007/s00706-017-2132-4

  日期：2018.4

  AbstractA novel approach to the neolignan-core skeletons of boehmenan natural products and to dehydrodiconiferyl alcohol glucosides based on the Fe(III)-promoted oxidative coupling has been achieved. Obtained common intermediates were further selectively modified to yield the basic molecular core possessing three orthogonally protected alkoxy functionalities available for further selective modifications

  摘要已经实现了一种新的方法来制备波美南天然产物的新木脂素核心骨架和基于Fe（III）促进的氧化偶合的去氢二松香酚醇葡糖苷。将获得的常见中间体进一步选择性修饰，以产生具有三个正交保护的烷氧基官能团的碱性分子核，可用于进一步的选择性修饰。 图形概要