4-(o-acetoxyphenyl)-2-methyl-3-butyn-2-ol | 251997-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(o-acetoxyphenyl)-2-methyl-3-butyn-2-ol
• 英文别名: [2-(3-Hydroxy-3-methylbut-1-ynyl)phenyl] acetate
• CAS: 251997-64-5
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: WKOMZJATILWPBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(o-acetoxyphenyl)-2-methyl-3-butyn-2-ol 在 palladium diacetate 、 甲酸 、 三正丁胺 、 碳酸氢钠 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 3-(4-Methoxyphenyl)-2,2-dimethylchromene
  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：

  1-乙酰氧基-2-碘苯 、 2-甲基-3-丁炔-2-醇 在 钯 作用下， 以81%的产率得到4-(o-acetoxyphenyl)-2-methyl-3-butyn-2-ol
  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

• Palladium-Catalyzed Hydrovinylation of Vinyl Triflates with Alkynes An Approach to the Synthesis of 3-Vinylfuran-2(5H)-ones
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Fabio Marinelli、Paola Pace

  DOI：10.1002/(sici)1099-0690(199912)1999:12<3305::aid-ejoc3305>3.0.co;2-o

  日期：1999.12

  The reaction of alkynes with vinyl triflates in the presence of catalytic amounts of Pd(OAc)2 and HCOOK, omitting phosphane ligands, affords hydrovinylation products usually in good to high yields. The reaction has been employed to develop a regioselective synthesis of 3-vinylfuran-2(5H)-ones from methyl 4-hydroxy-2-butynoates.

  在催化量的 Pd(OAc)2 和 HCOOK 存在下，炔烃与乙烯基三氟甲磺酸酯的反应，省略磷烷配体，通常以良好到高产率提供加氢乙烯基化产物。该反应已被用于从 4-羟基-2-丁酸甲酯开发 3-乙烯基呋喃-2(5H)-酮的区域选择性合成。
• Copper(II) Bromide Catalyzed Novel Preparation of Propargylic Ethers and Sulfides by S_N1-Type Substitution between Propargylic Alcohols and Alcohols or Thiols
  作者：Guo-sheng Huang、Hao-hao Hui、Qin Zhao、Ming-yu Yang、De-bing She、Min Chen

  DOI：10.1055/s-2007-990951

  日期：2008.1

  A general and efficient copper(II) bromide catalyzed substitution reaction of propargylic alcohols with carbon and heteroatom-centered nucleophiles, such as alcohols and thiols, leading to the construction of C-O and C-S bonds has been developed. High product yields were obtained with excellent regioselectivity.

  已经开发了一种通用且高效的溴化铜 (II) 催化炔丙醇与碳和以杂原子为中心的亲核试剂（如醇和硫醇）的取代反应，从而构建 CO 和 CS 键。以优异的区域选择性获得了高产率。
• 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.