4-(2,2-dibromovinyl)phenyl 4-methylbenzenesulfonate | 1430102-36-5

• 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: 4-(2,2-dibromovinyl)phenyl 4-methylbenzenesulfonate
• CAS: 1430102-36-5
• 化学式: C₁₅H₁₂Br₂O₃S
• 分子量: 432.132
• InChiKey: CRXRLQDEILSRTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(2,2-dibromovinyl)phenyl 4-methylbenzenesulfonate 在 四(二甲氨基)乙烯 、 nickel(II) bis(bromide) (3aR,3a’R,8aS,8a’S)-2,2’-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 、 三乙胺 、 亚磷酸二乙酯 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.17h， 生成 (S,E)-4-(3-phenylbut-1-en-1-yl)phenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

  摘要：

  An enantioselective Ni-catalyzed cross-coupling of NT-hyciroxyphthalimide esters with Vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetralds(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.

  DOI：

  10.1021/acs.orglett.7b00793
• 作为产物：
  描述：

  四溴化碳 、 4-tosyloxybenzaldehyde 在 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以77%的产率得到4-(2,2-dibromovinyl)phenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

  摘要：

  An enantioselective Ni-catalyzed cross-coupling of NT-hyciroxyphthalimide esters with Vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetralds(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.

  DOI：

  10.1021/acs.orglett.7b00793

文献信息

• A Highly Reduced Ni–Li–Olefin Complex for Catalytic Kumada–Corriu Cross-Couplings
  作者：Lukas Nattmann、Sigrid Lutz、Pascal Ortsack、Richard Goddard、Josep Cornella

  DOI：10.1021/jacs.8b09849

  日期：2018.10.24

  The catalytic activity of a highly reduced Ni catalyst in the context of a Kumada-Corriu cross coupling has been studied. This nickel complex is characterized by its high electron density, stabilized by simple olefin ligands in combination with two Li ions. Landmark reactivity has been found with this precatalyst which operates at cryogenic temperatures, thus allowing the presence of sensitive functionalities. Structural elucidation of oxidative addition intermediates and their reactivity suggest highly reduced species being operative in the C-C bond forming event.
• Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes
  作者：Zheng Huang、Rui Shang、Zi-Rong Zhang、Xiao-Dan Tan、Xiao Xiao、Yao Fu

  DOI：10.1021/jo400616r

  日期：2013.5.3

  A copper-catalyzed decarboxylative coupling reaction of potassium alkynyl carboxylates with 1,1-dibromo-1-alkenes was developed for the synthesis of unsymmetrical 1,3-diyne and 1,3,5-triyne derivatives. Diverse aryl, alkenyl, alkynyl, and alkyl substituted 1,1-dibromo-1-alkenes can react smoothly with aryl and alkyl substituted propiolates to produce unsymmetrical 1,3-diynes and 1,3,5-triynes with high selectivity and good functional group compatibility.