Ethyl 2-(4-methylphenyl)sulfonyl-2-(4-phenylphenyl)acetate | 447465-00-1

• 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: Ethyl 2-(4-methylphenyl)sulfonyl-2-(4-phenylphenyl)acetate
• CAS: 447465-00-1
• 化学式: C₂₃H₂₂O₄S
• 分子量: 394.491
• InChiKey: YBNHRDXUDYEFBC-UHFFFAOYSA-N

物化性质

• 沸点：
  583.7±50.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  Ethyl 2-(4-methylphenyl)sulfonyl-2-(4-phenylphenyl)acetate 在 magnesium 、 mercury dichloride 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以30%的产率得到4-联苯乙酸
  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
• 作为产物：
  描述：

  对溴溴苄 在 di-μ-chlorobis{(acetophenone oxime)palladium(II)} 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 Ethyl 2-(4-methylphenyl)sulfonyl-2-(4-phenylphenyl)acetate
  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.