3,5-di-O-acetylresveratrol | 1246833-37-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,5-di-O-acetylresveratrol
• 英文别名: 3,5-Diacetoxy-4'-hydroxy stilbene；[3-acetyloxy-5-[2-(4-hydroxyphenyl)ethenyl]phenyl] acetate
• CAS: 1246833-37-3
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: YBTSXNIAKDYGPK-UHFFFAOYSA-N

物化性质

• 沸点：
  483.3±45.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-di-O-acetylresveratrol 在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 生成 resveratrol
  参考文献：
  名称：

  WO2007/110883

  摘要：

  公开号：
• 作为产物：
  描述：

  对羟基苯乙酸 、 3,5-diacetoxybenzaldehyde 在 哌啶 、 N-甲基咪唑 作用下， 反应 0.15h， 以66%的产率得到3,5-di-O-acetylresveratrol
  参考文献：
  名称：

  WO2007/110883

  摘要：

  公开号：

文献信息

• Utilization of the inherent nucleophile for regioselective O-acylation of polyphenols via an intermolecular cooperative transesterification
  作者：Jingchao Liu、Junjie Fu、Wenlong Li、Yu Zou、Zhangjian Huang、Jinyi Xu、Sixun Peng、Yihua Zhang

  DOI：10.1016/j.tet.2016.05.048

  日期：2016.7

  A green and efficient method for regioselective O-acylation of polyphenols has been developed. The acylation can be carried out in potassium carbonate/dimethyl sulphoxide system by utilizing the ‘inherent nucleophile’ via an intermolecular cooperative transesterification under mild condition. This method shows particular advantage in regioselective acylation of polyphenols bearing 2′,4′-dihydroxyacetophenone

  已经开发了一种绿色有效的多酚区域选择性O-酰化方法。可以在温和条件下通过分子间合作酯交换利用“固有亲核试剂”，在碳酸钾/二甲亚砜体系中进行酰化反应。该方法在带有2'，4'-二羟基苯乙酮部分的多酚的区域选择性酰化中显示出特别的优势，并且可以扩展为不具有该部分的多酚的单乙酸酯或多种乙酸酯的合成。与其他已报道的方法相比，该方法具有原子经济性，并且在避免使用任何金属基催化剂方面更加环保。
• Hydrogen atom abstraction from resveratrol and two lipophilic derivatives by tert-butoxyl radicals. A laser flash photolysis study.
  作者：Salvatore Petralia、Carmela Spatafora、Corrado Tringali、Mario C. Foti、Salvatore Sortino

  DOI：10.1039/b410802g

  日期：——

  The reactions of tert-butoxyl radicals with resveratrol (1) and two acetylated derivatives (2 and 3) have been investigated by laser flash photolysis techniques in 1∶2 (v/v) benzene–di-tert-butyl peroxide at room temperature. The transient absorption spectra of the phenoxyl radicals generated upon H atom abstraction by tert-butoxyl radicals from the phenols have been detected and assigned. The absolute

  的反应中叔-butoxyl自由基与白藜芦醇（1）和两种乙酰化衍生物（2和3）已通过激光闪光光解 1∶2（v / v）中的技巧 苯–二-叔丁基过氧化在室温下。瞬态吸收光谱叔丁氧基从氢原子夺取H原子时产生的苯氧基酚类已被检测到并已分配。绝对速率常数用于这些反应已被评估为45×10 7，25×10 7 4×10 7中号-1小号-1为1，2和3分别。反应性的顺序1 ≥ 2 » 3已被合理化，在芳环上的乙酰基的位置和作用方面。存在于三个OH基团中白藜芦醇，由于相应的苯氧基自由基通过与环的共轭具有很大的稳定性，因此位置4'的一个反应性最高。但是，在我们的系统中，白藜芦醇事实证明，其在α-生育酚方面逊色于α-生育酚。一个数量级。
• Novel Sirtuin Activating Compounds and Methods for Making the Same
  申请人：Andrus Merritt B.

  公开号：US20080255382A1

  公开（公告）日：2008-10-16

  The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from P n , R or absent, each V and each W is independently selected from P n , straight or branched alkyl of from (2) to (6) carbon atoms and cycloalkyl of from (3) to (8) carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, P n is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbon-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.

  本发明涉及制备白藜芦醇、白藜芦醇酯和给定公式的取代和未取代的苯乙烯衍生物的方法; 其中每个Y是—O或卤素，每个Z是—O或卤素，每个n和每个m独立地取值为0、1、2、3、4或5，每个A和每个B独立地从Pn、R或不存在中选择，每个V和每个W独立地从(2)到(6)碳原子的直链或支链烷基、(3)到(8)碳原子的环烷基、烷氧基、苯基、苄基或卤素中选择，R独立地从包括至少一个碳原子的烷基、芳基和芳基烷基的群中选择，Pn是醇保护基和上述化合物的对映异构体。这些化合物是通过多步反应制备而成，其中包括在碱的存在下使用苯甲酰卤和苯乙烯偶合物进行N-杂环碳型配体偶合。这些化合物在食品、化妆品和制药工业中具有增强的稳定性。
• NOVEL SIRTUIN ACTIVATING COMPOUNDS AND PROCESSES FOR MAKING THE SAME
  申请人：Andrus Merritt B.

  公开号：US20100185006A1

  公开（公告）日：2010-07-22

  The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from P n , R or absent, each V and each W is independently selected from P n , straight or branched alkyl of from 2 to 6 carbon atoms and cycloalkyl of from 3 to 8 carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, P n is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbene-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.

  本发明涉及制备白藜芦醇、白藜芦醇酯和给出下列式子的取代和未取代的苯乙烯的方法；其中每个Y是—O或卤素，每个Z是—O或卤素，每个n和每个m是独立地取值为0、1、2、3、4或5，每个A和每个B是独立地从Pn、R或缺失中选择，每个V和每个W是独立地从Pn、2到6个碳原子的直链或支链烷基和3到8个碳原子的环烷基、烷氧基、苯基、苄基或卤素中选择，R是独立地从包括至少一个碳原子的烷基、芳基和芳基烷基的群体中选择，Pn是醇保护基和上述化合物的对映异构体。这些化合物是通过多步反应制备的，包括在碱存在下与苯乙烯偶联反应的N-杂环卡宾型配体偶联反应。这些化合物表现出增强的稳定性，可用于食品、化妆品和制药工业中。
• Sirtuin activating compounds and processes for making the same
  申请人：Andrus Merritt B.

  公开号：US08841477B2

  公开（公告）日：2014-09-23

  The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from Pn, R or absent, each V and each W is independently selected from Pn, straight or branched alkyl of from 2 to 6 carbon atoms and cycloalkyl of from 3 to 8 carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, Pn is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbene-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.

  本发明涉及制备白藜芦醇、白藜芦醇酯和给出的式子中的取代和未取代的苯乙烯衍生物的方法;其中每个Y是—O或卤素，每个Z是—O或卤素，每个n和每个m独立地取值为0、1、2、3、4或5，每个A和每个B独立地选择自Pn、R或不存在，每个V和每个W独立地选择自Pn、2到6个碳原子的直链或支链烷基和3到8个碳原子的环烷基、烷氧基、苯基、苄基或卤素，R独立地选择自包括至少一个碳原子的烷基、芳基和芳基烷基的群，Pn是醇保护基和上述化合物的对映异构体。这些化合物通过多步反应制备，包括在碱的存在下与苯乙烯偶联合成苯甲酰卤和苯乙烯偶联配对的N-杂环卡宾型配体偶联。这些化合物在食品、化妆品和制药行业中显示出增加的稳定性。