Benzoic acid 4-cyano-2-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl ester | 328077-59-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: Benzoic acid 4-cyano-2-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl ester
• 英文别名: [4-Cyano-2-(3-hydroxy-3-methylbut-1-ynyl)phenyl] benzoate
• CAS: 328077-59-4
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: XNFVNVWUVRECQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid 4-cyano-2-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl ester 在 palladium diacetate 、 甲酸 、 三正丁胺 、 正丁胺 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 4-(4-Methoxy-phenyl)-2,2-dimethyl-2H-chromene-6-carbonitrile
  参考文献：
  名称：

  The Palladium-Catalyzed Hydroarylation and Hydrovinylation of Tertiary 3-(o-Acetoxyaryl)- and 3-(o-Benzoyloxyaryl)propynols − A Route to 4-Aryl- and 4-Vinyl-2,2-Dimethyl-3-chromenes

  摘要：

  The palladium-catalyzed hydroarylation and hydrovinylation of tertiary 3-(o-acetoxyaryl)- and 3-(o-benzoyloxyaryl) propynols provides a regio- and stereoselective route to allylic alcohols with aryl and vinyl substituents which can be readily converted into the corresponding chromene derivatives. The hydroarylation and hydrovinylation reaction is believed to proceed through a carbopalladation step whose regiochemistry is primarily controlled by the directing effect of the tertiary hydroxy group.

  DOI：

  10.1002/1099-0690(200012)2000:24<4099::aid-ejoc4099>3.0.co;2-n
• 作为产物：
  描述：

  2-甲基-3-丁炔-2-醇 、 benzoic acid 4-cyano-2-iodo-phenyl ester 在 copper(l) iodide 作用下， 以82%的产率得到Benzoic acid 4-cyano-2-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl ester
  参考文献：
  名称：

  The Palladium-Catalyzed Hydroarylation and Hydrovinylation of Tertiary 3-(o-Acetoxyaryl)- and 3-(o-Benzoyloxyaryl)propynols − A Route to 4-Aryl- and 4-Vinyl-2,2-Dimethyl-3-chromenes

  摘要：

  The palladium-catalyzed hydroarylation and hydrovinylation of tertiary 3-(o-acetoxyaryl)- and 3-(o-benzoyloxyaryl) propynols provides a regio- and stereoselective route to allylic alcohols with aryl and vinyl substituents which can be readily converted into the corresponding chromene derivatives. The hydroarylation and hydrovinylation reaction is believed to proceed through a carbopalladation step whose regiochemistry is primarily controlled by the directing effect of the tertiary hydroxy group.

  DOI：

  10.1002/1099-0690(200012)2000:24<4099::aid-ejoc4099>3.0.co;2-n

文献信息

• The Palladium-Catalyzed Hydroarylation and Hydrovinylation of Tertiary 3-(o-Acetoxyaryl)- and 3-(o-Benzoyloxyaryl)propynols − A Route to 4-Aryl- and 4-Vinyl-2,2-Dimethyl-3-chromenes
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Fabio Marinelli、Paola Pace

  DOI：10.1002/1099-0690(200012)2000:24<4099::aid-ejoc4099>3.0.co;2-n

  日期：2000.12

  The palladium-catalyzed hydroarylation and hydrovinylation of tertiary 3-(o-acetoxyaryl)- and 3-(o-benzoyloxyaryl) propynols provides a regio- and stereoselective route to allylic alcohols with aryl and vinyl substituents which can be readily converted into the corresponding chromene derivatives. The hydroarylation and hydrovinylation reaction is believed to proceed through a carbopalladation step whose regiochemistry is primarily controlled by the directing effect of the tertiary hydroxy group.