(Z)-oct-3-ene-3,4-diyldibenzene | 1427179-75-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-oct-3-ene-3,4-diyldibenzene
• 英文别名: [(Z)-3-phenyloct-3-en-4-yl]benzene
• CAS: 1427179-75-6
• 化学式: C₂₀H₂₄
• 分子量: 264.411
• InChiKey: KSCVRUUQMZYQAF-VXPUYCOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-苯基丁酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 4-二甲氨基吡啶 、 正丁基锂 、 palladium diacetate 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 58.0h， 生成 (Z)-oct-3-ene-3,4-diyldibenzene
  参考文献：
  名称：

  Stereoselective Synthesis of All-Carbon Tetrasubstituted Alkenes from In Situ Generated Ketenes and Organometallic Reagents

  摘要：

  Stereoselective synthesis of tetrasubstituted alkenes is a challenging problem in chemical synthesis. New protocols to access this Important, yet simple, structural motif are of fundamental significance because they are found In many valuable molecules and can be utilized in a variety of Important complexity building chemical transformations. The two-step strategy presented herein involves stereoselective generation of an alkenyl pseudohalide followed by a stereospecific metal-catalyzed cross-coupling.

  DOI：

  10.1021/ol400392r

文献信息

• Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki–Miyaura Coupling
  作者：Beryl X. Li、Diane N. Le、Kyle A. Mack、Andrew McClory、Ngiap-Kie Lim、Theresa Cravillion、Scott Savage、Chong Han、David B. Collum、Haiming Zhang、Francis Gosselin

  DOI：10.1021/jacs.7b05071

  日期：2017.8.9

  A highly stereocontrolled synthesis of tetrasubstituted acyclic all-carbon olefins has been developed via a stereoselective enolization and tosylate formation, followed by a palladium-catalyzed Suzuki-Miyaura cross-coupling of the tosylates and pinacol boronic esters in the presence of a Pd(OAc)2/RuPhos catalytic system. Both the enol tosylation and Suzuki-Miyaura coupling reactions tolerate an array

  通过立体选择性烯醇化和甲苯磺酸酯形成，然后在 Pd(OAc)2 存在下对甲苯磺酸酯和频哪醇硼酯进行钯催化的 Suzuki-Miyaura 交叉偶联，开发了四取代无环全碳烯烃的高度立体控制合成2/RuPhos催化系统。烯醇甲苯磺酰化和铃木-宫浦偶联反应均可耐受一系列电子和空间上不同的取代基，并产生高产率和立体选择性的烯烃产物。明智地选择底物和偶联伙伴可以以优异的产率和立体化学保真度获得E-或Z-烯烃。在铃木-宫浦偶联过程中观察到烯烃异构化。然而，在优化的交叉偶联反应条件下，大多数情况下异构化被抑制到<5%。机理探针表明烯烃异构化是通过中间体发生的，该中间体可能是两性离子钯类胡萝卜素物质。
• Stereoselective Synthesis of All-Carbon Tetrasubstituted Alkenes from In Situ Generated Ketenes and Organometallic Reagents
  作者：Wei You、Yan Li、M. Kevin Brown

  DOI：10.1021/ol400392r

  日期：2013.4.5

  Stereoselective synthesis of tetrasubstituted alkenes is a challenging problem in chemical synthesis. New protocols to access this Important, yet simple, structural motif are of fundamental significance because they are found In many valuable molecules and can be utilized in a variety of Important complexity building chemical transformations. The two-step strategy presented herein involves stereoselective generation of an alkenyl pseudohalide followed by a stereospecific metal-catalyzed cross-coupling.