(Z)-1-methyl-2-(4-methoxyphenyl)ethenyl tosylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1-methyl-2-(4-methoxyphenyl)ethenyl tosylate
• 英文别名: (Z)-1-(4-methoxyphenyl)-1-propen-2-yl tosylate；(Z)-1-(4-methoxyphenyl)prop-1-en-2-yl-4-methyl benzenesulfonate；[(Z)-1-(4-methoxyphenyl)prop-1-en-2-yl] 4-methylbenzenesulfonate
• 化学式: C₁₇H₁₈O₄S
• 分子量: 318.394
• InChiKey: ZKUBDLMTAMCQQG-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-1-methyl-2-(4-methoxyphenyl)ethenyl tosylate 、 2-吡咯烷酮 在 tris-(dibenzylideneacetone)dipalladium(0) 3-氟-4-甲氧基苯乙酮 、 potassium carbonate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 20.0h， 以98%的产率得到(Z)-N-[1-methyl-2-(4-methoxyphenyl)ethenyl]-2-pyrrolidinone
  参考文献：
  名称：

  Preparation of Enamides via Palladium-Catalyzed Amidation of Enol Tosylates

  摘要：

  [GRAPHICS]A Pd-catalyzed coupling of enol tosylates and amides has been developed. Ligand screening revealed dipf as the most general ligand for this transformation. A variety of enol tosylates were coupled to an array of enamides in 58-97% yield.

  DOI：

  10.1021/ol050117y
• 作为产物：
  描述：

  对甲氧基苯基丙酮 、 4-甲苯磺酸酐 在 sodium t-butanolate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 5.5h， 以69%的产率得到(Z)-1-methyl-2-(4-methoxyphenyl)ethenyl tosylate
  参考文献：
  名称：

  Preparation of Enamides via Palladium-Catalyzed Amidation of Enol Tosylates

  摘要：

  [GRAPHICS]A Pd-catalyzed coupling of enol tosylates and amides has been developed. Ligand screening revealed dipf as the most general ligand for this transformation. A variety of enol tosylates were coupled to an array of enamides in 58-97% yield.

  DOI：

  10.1021/ol050117y

文献信息

• Palladium Catalyzed Alkoxy- and Aminocarbonylation of Vinyl Tosylates
  作者：Diana C. Reeves、Sonia Rodriguez、Heewon Lee、Nizar Haddad、Dhileepkumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1021/ol200744s

  日期：2011.5.6

  The palladium catalyzed alkoxycarbonylation and aminocarbonylation of vinyl tosylates are described. A variety of ketone and aldehyde derived vinyl tosylates may be carbonylated in the presence of primary, secondary, and tertiary alcohols, or primary and secondary amines, to provide the corresponding esters and amides in good yields. The alkoxycarbonylation was applied to a short synthesis of isoguvacine

  描述了甲苯磺酸乙烯基酯的钯催化的烷氧基羰基化和氨基羰基化。在伯，仲和叔醇，或伯和仲胺的存在下，各种酮和醛衍生的乙烯基甲苯磺酸酯可以被羰基化，以高收率提供相应的酯和酰胺。将烷氧羰基化用于异古瓦汀的短合成。
• Preparation of Enamides via Palladium-Catalyzed Amidation of Enol Tosylates
  作者：Artis Klapars、Kevin R. Campos、Cheng-yi Chen、Ralph P. Volante

  DOI：10.1021/ol050117y

  日期：2005.3.1

  [GRAPHICS]A Pd-catalyzed coupling of enol tosylates and amides has been developed. Ligand screening revealed dipf as the most general ligand for this transformation. A variety of enol tosylates were coupled to an array of enamides in 58-97% yield.