3,5-bis(methoxymethoxy)-4'-acetoxy stilbene | 861446-18-6

• 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-bis(methoxymethoxy)-4'-acetoxy stilbene
• 英文别名: 3,5-bis(methoxymethoxy)-4'-acetoxystilbene；(E)-4-(3,5-bis(methoxymethoxy)styryl)phenol acetate；E-4'-acetoxy-3,5-bis(methoxymethoxy)stilbene；4'-acetoxy-3,5-bis(methoxymethoxy)stilbene；[4-[(E)-2-[3,5-bis(methoxymethoxy)phenyl]ethenyl]phenyl] acetate
• CAS: 861446-18-6
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: TZTGESNRHUMVJV-SNAWJCMRSA-N

物化性质

• 沸点：
  507.1±50.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-bis(methoxymethoxy)-4'-acetoxy stilbene 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以95%的产率得到(E)-4-(3,5-bis(methoxymethoxy)styryl)phenol
  参考文献：
  名称：

  白藜芦醇4'-酯类似物的合成及其在恶性黑色素瘤和胰腺细胞株中的评价

  摘要：

  合成了疾病预防剂白藜芦醇的4'-酯类似物，并评估了其作为抗黑素瘤和胰腺癌药物的潜力。使用脱羰Heck偶联剂组装受保护的二苯乙烯核结构。与正常的NHDF细胞相比，DM443和DM738细胞具有4'-乙酸和棕榈酸酯类似物的选择性活性。

  DOI：

  10.1016/j.bmcl.2009.12.006
• 作为产物：
  描述：

  3,5-bis(methoxymethoxy)benzoic acid 在 palladium diacetate N-甲基吗啉 、 T406石油添加剂 、 氯化亚砜 、 1,3-双-(2,6-二异丙基苯基)咪唑鎓氯化物 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 3.67h， 生成 3,5-bis(methoxymethoxy)-4'-acetoxy stilbene
  参考文献：
  名称：

  Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings

  摘要：

  Protected 3,5-hydroxy-benzoyl chlorides 3 were coupled with styrenes 4 to give hydroxylated stilbenes, analogs of resveratrol, an important antioxidant disease preventative agent isolated from grape skins and other dietary sources. Levulinate and chloroacetate protecting groups allowed for the selective production of mono- and di-acetate variations under palladium-N-heterocyclic carbene (NHC) catalyzed decarbonylative coupling conditions. Fluorinated analogs were also produced using Heck conditions with bromofluorobenzenes. Human HL-60 cell assays showed the 4'-acetoxy variant 11 to have improved activity (ED50 17 mu M) relative to resveratrol (24 mu M). (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.05.065

文献信息

• 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.

  本发明涉及一种制备白藜芦醇、白藜芦醇酯和给定以下结构式的取代和未取代的stilbenes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或缺席中选择，每个V和每个W独立地从Pn、由（2）到（6）个碳原子的直链或支链烷基和由（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过程制备的，其中包括在碱存在下与苄基卤和苯乙烯偶联合成N-杂环碳型配体偶联。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。
• Methods for Providing Enhanced Resveratrol Activity Using 4-Acetoxy-Resveratrol
  申请人：Lephart Edwin Douglas

  公开号：US20130123357A1

  公开（公告）日：2013-05-16

  The present invention relates to a method of providing enhanced resveratrol activity comprising: administering a therapeutically effective amount of 4-acetoxy-resveratrol for the treatment of and preventing physiological and pathophysiological conditions mediated by (1) sirtuins, (2) estrogen and anti-estrogen hormone actions and (3) chemical interventions important for male and female health, aging, anti-aging and age-related disorders.

  本发明涉及一种提供增强白藜芦醇活性的方法，包括：通过给予治疗有效量的4-乙酰氧基白藜芦醇来治疗和预防由(1)sirtuins、(2)雌激素和抗雌激素激素作用以及(3)对男性和女性健康、衰老、抗衰老和与年龄相关的疾病重要的化学干预介导的生理和病理生理状态。
• NOVEL SIRTUIN ACTIVATING COMPOUNDS AND METHODS FOR MAKING THE SAME
  申请人：Brigham Young University

  公开号：EP1753708A2

  公开（公告）日：2007-02-21
• EP1753708A4
  申请人：——

  公开号：EP1753708A4

  公开（公告）日：2007-12-26