3-(4-chloro-phenyl)-2-methanesulfonyl-pent-4-enoic acid ethyl ester | 1164111-57-2

• 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: 3-(4-chloro-phenyl)-2-methanesulfonyl-pent-4-enoic acid ethyl ester
• 英文别名: Ethyl 3-(4-chlorophenyl)-2-methylsulfonylpent-4-enoate；ethyl 3-(4-chlorophenyl)-2-methylsulfonylpent-4-enoate
• CAS: 1164111-57-2
• 化学式: C₁₄H₁₇ClO₄S
• 分子量: 316.806
• InChiKey: OOXJPCXVCLYART-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-(4-chloro-phenyl)-2-methanesulfonyl-pent-4-enoic acid ethyl ester 、 dithiocarbonic acid S-[2-(4-bromo-phenyl)-2-oxo-ethyl] ester O-ethyl ester 在 过氧化双月桂酰 作用下， 以 氯苯 为溶剂， 反应 2.5h， 以59%的产率得到(E)-7-(4-bromo-phenyl)-4-(4-chloro-phenyl)-7-oxo-hept-2-enoic acid ethyl ester
  参考文献：
  名称：

  A Convergent Radical-Based Route to Biaryls

  摘要：

  A route to biaryl-3-carboxylate esters involving a radical 1,2-aryl migration has been developed. This strategy hinges on the radical addition of xanthate 2 to olefin 1 causing a 1,2-aryl shift leading to alpha,beta-unsaturated ester 5, which is then converted into biaryl 10 by treatment with DBU under microwave heating.

  DOI：

  10.1021/ol9010294
• 作为产物：
  描述：

  乙烯基溴化镁 、 2-methanesulfonyl-3-(4-chlorophenyl)-acrylic acid ethyl ester 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到3-(4-chloro-phenyl)-2-methanesulfonyl-pent-4-enoic acid ethyl ester
  参考文献：
  名称：

  A Convergent Radical-Based Route to Biaryls

  摘要：

  A route to biaryl-3-carboxylate esters involving a radical 1,2-aryl migration has been developed. This strategy hinges on the radical addition of xanthate 2 to olefin 1 causing a 1,2-aryl shift leading to alpha,beta-unsaturated ester 5, which is then converted into biaryl 10 by treatment with DBU under microwave heating.

  DOI：

  10.1021/ol9010294

文献信息

• Radical-Based Route to 2-(Trifluoromethyl)-1,3,4-oxadiazoles and Trifluoromethyl-Substituted Polycyclic 1,2,4-Triazoles and Dihydrofurans
  作者：Ling Qin、Samir Z. Zard

  DOI：10.1021/acs.orglett.5b00457

  日期：2015.3.20

  O-Ethyl S-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl xanthate was readily prepared on a large scale and shown to undergo very efficient intermolecular radical additions to unactivated alkenes. The products were further elaborated by exploiting both radical and ionic processes to provide a variety of trifluoromethyl-substituted derivatives, including medicinally relevant triazoles. In particular, the application of a radical allylation on the initial adducts leads to structures that are able to undergo intramolecular [4 + 2] cycloaddition reactions.
• A Convergent Radical-Based Route to Biaryls
  作者：Béatrice Quiclet-Sire、Guillaume Revol、Samir Z. Zard

  DOI：10.1021/ol9010294

  日期：2009.7.2

  A route to biaryl-3-carboxylate esters involving a radical 1,2-aryl migration has been developed. This strategy hinges on the radical addition of xanthate 2 to olefin 1 causing a 1,2-aryl shift leading to alpha,beta-unsaturated ester 5, which is then converted into biaryl 10 by treatment with DBU under microwave heating.