4-chloroacetoxystyrene | 861446-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-chloroacetoxystyrene
• 英文别名: (4-ethenylphenyl) 2-chloroacetate
• CAS: 861446-20-0
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: CGOXQUPHAKMSBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloroacetoxystyrene 在 palladium diacetate N-甲基吗啉 、 吡啶 、 水 、 1,3-双-(2,6-二异丙基苯基)咪唑鎓氯化物 作用下， 以 xylene 为溶剂， 反应 9.5h， 生成 3,5-di-O-acetylresveratrol
  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
• 作为产物：
  描述：

  4-乙酰氧基苯乙烯 在 氢氧化钾 、 水 、 三乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.5h， 生成 4-chloroacetoxystyrene
  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。
• 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。
• Sirtuin activating compounds and methods for making the same
  申请人：Brigham Young University

  公开号：US07714161B2

  公开（公告）日：2010-05-11

  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、白藜芦醇酯和下列公式的取代和未取代的苯乙烯类化合物的方法；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或缺失，每个V和每个W独立地选择自Pn、(2)至(6)碳原子的直链或支链烷基和(3)至(8)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过程制备，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。这些化合物在食品、化妆品和制药行业中具有增加的稳定性。
• 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