ethyl (E)-3-[2-(p-toluenesulfonylmethyl)phenyl]-2-propenoate | 447464-51-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-3-[2-(p-toluenesulfonylmethyl)phenyl]-2-propenoate
• 英文别名: ethyl (E)-3-[2-[(4-methylphenyl)sulfonylmethyl]phenyl]prop-2-enoate
• CAS: 447464-51-9
• 化学式: C₁₉H₂₀O₄S
• 分子量: 344.431
• InChiKey: SAAMPRZBDRMRAK-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴乙酸叔丁酯 、 ethyl (E)-3-[2-(p-toluenesulfonylmethyl)phenyl]-2-propenoate 在 1-叔丁基-2,2,4,4,4-五(二甲氨基)-2Λ5,4Λ5-连二(磷氮基化合物) 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (E)-3-{2-[(E)-2-(tert-butoxycarbonyl)-1-ethenyl]phenyl}-2-propenoate
  参考文献：
  名称：

  P2-Et-Mediated Deprotonation of ortho-Halobenzyl Sulfones: Synthetic Applications as Zwitterionic Synthons

  摘要：

  α-磺酰基苄基碳负离子，源自邻卤代苄基砜 5 (Hal = Br, I)，可以很容易地由磷腈碱 P2-Et 生成，并与不同的亲电子试剂如烷基卤、醛和丙烯酸乙酯发生反应。在卤素原子上进行钯催化的交叉偶联反应，然后使用溴乙酸盐作为亲电子试剂进行 P2-Et 介导的烷基化-脱氢亚磺酰化过程，可以制备邻位取代的肉桂酸酯。

  DOI：

  10.1055/s-2001-18740
• 作为产物：
  描述：

  sodium 4-methylbenzenesulfinate 在 palladium diacetate 、 四丁基溴化铵 、 氢溴酸 、 potassium carbonate 、 三苯基膦 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 67.0h， 生成 ethyl (E)-3-[2-(p-toluenesulfonylmethyl)phenyl]-2-propenoate
  参考文献：
  名称：

  Synthetic Applications of o- and p-Halobenzyl Sulfones as Zwitterionic Synthons:  Preparation of Ortho-Substituted Cinnamates and Biarylacetic Acids

  摘要：

  The synthetic applications of o-halobenzyl and p-halobenzyl sulfones as precursors of 1,3- and 1,5-zwitterionic synthons, respectively, are described. Their alpha-sulfonyl carbanions, generated by means of the phosphazene base P-2-Et or BuLi or K2CO3 under PTC conditions, reacted with different electrophiles such as alkyl halides, aldehydes, and electrophilic olefins. Palladium-catalyzed cross-coupling processes such as Heck, Suzuki, and Sonogashira reactions can be efficiently performed at the halogen atom. These two sequential functionalization processes are applied to the synthesis of ortho-substituted cinnamates and pharmaceuticals belonging to the family of p-biarylacetic acids such as 4-biphenylacetic acid, namoxyrate, xenyhexenic acid, and bipherylpropionic acid.

  DOI：

  10.1021/jo025620s

文献信息

• Synthetic Applications of <i>o-</i> and <i>p</i>-Halobenzyl Sulfones as Zwitterionic Synthons:  Preparation of <i>O</i><i>rtho-</i>Substituted Cinnamates and Biarylacetic Acids
  作者：Ana Costa、Carmen Nájera、José M. Sansano

  DOI：10.1021/jo025620s

  日期：2002.7.1

  The synthetic applications of o-halobenzyl and p-halobenzyl sulfones as precursors of 1,3- and 1,5-zwitterionic synthons, respectively, are described. Their alpha-sulfonyl carbanions, generated by means of the phosphazene base P-2-Et or BuLi or K2CO3 under PTC conditions, reacted with different electrophiles such as alkyl halides, aldehydes, and electrophilic olefins. Palladium-catalyzed cross-coupling processes such as Heck, Suzuki, and Sonogashira reactions can be efficiently performed at the halogen atom. These two sequential functionalization processes are applied to the synthesis of ortho-substituted cinnamates and pharmaceuticals belonging to the family of p-biarylacetic acids such as 4-biphenylacetic acid, namoxyrate, xenyhexenic acid, and bipherylpropionic acid.
• P2-Et-Mediated Deprotonation of ortho-Halobenzyl Sulfones: Synthetic Applications as Zwitterionic Synthons
  作者：Ana Costa、Carmen Nájera、José M. Sansano

  DOI：10.1055/s-2001-18740

  日期：——

  α-Sulfonyl benzylic carbanions, derived from ortho-halobenzyl sulfones 5 (Hal = Br, I), can be easily generated by the phosphazene base P2-Et and react with different electrophiles such as alkyl halides, aldehydes and ethyl acrylate. Palladium catalysed cross-coupling reactions performed at the halogen atom, followed by P2-Et-mediated alkylation-dehydrosulfinylation process using bromoacetates as electrophiles allow the preparation of ortho-substituted cinnamates.

  α-磺酰基苄基碳负离子，源自邻卤代苄基砜 5 (Hal = Br, I)，可以很容易地由磷腈碱 P2-Et 生成，并与不同的亲电子试剂如烷基卤、醛和丙烯酸乙酯发生反应。在卤素原子上进行钯催化的交叉偶联反应，然后使用溴乙酸盐作为亲电子试剂进行 P2-Et 介导的烷基化-脱氢亚磺酰化过程，可以制备邻位取代的肉桂酸酯。