(E)-9-styryl-9H-fluorene | 5751-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (E)-9-styryl-9H-fluorene
• 英文别名: trans-9-Styrylfluorene；9-[(E)-2-phenylethenyl]-9H-fluorene
• CAS: 5751-43-9
• 化学式: C₂₁H₁₆
• 分子量: 268.358
• InChiKey: ASIPTEKJTVITFH-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-(9H-fluoren-9-yl)-1-phenylethan-1-one 在 sodium tetrahydroborate 作用下， 生成 (E)-9-styryl-9H-fluorene
  参考文献：
  名称：

  9-苯乙芴及其脱氢衍生物

  摘要：

  合成了9-苯乙芴，9-苯乙叉芴，β-9-芴苯乙烯和螺-1-（9-芴基）-2-苯基环丙烷。关于2-（9-芴基）-1,1-二苯乙烯和2-芴基-1,1-二苯乙烷的某些错误陈述已得到纠正，并且与9-苯基亚乙基芴和β-9-芴基苯乙烯相比，这些物质的异构化1,3,3-和1,1,3-三苯基丙烯

  DOI：

  10.1039/j39660001810

文献信息

• Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles
  作者：Chengxi Li、Yuanyuan Zhang、Qi Sun、Tongnian Gu、Henian Peng、Wenjun Tang

  DOI：10.1021/jacs.6b06285

  日期：2016.8.31

  We herein report a transition-metal-free cross-coupling between secondary alkyl halides/mesylates and aryl/alkenylboronic acid, providing expedited access to a series of nonchiral/chiral coupling products in moderate to good yields. Stereospecific SN2-type coupling is developed for the first time with alkenylboronic acids as pure nucleophiles, offering an attractive alternative to the stereospecific

  我们在此报告了仲烷基卤化物/甲磺酸盐和芳基/烯基硼酸之间的无过渡金属交叉偶联，以中等至良好的产率快速获得一系列非手性/手性偶联产物。首次使用烯基硼酸作为纯亲核试剂开发了立体特异性 SN2 型耦合，为立体特异性过渡金属催化的 C(sp(2))-C(sp(3)) 交叉耦合提供了一种有吸引力的替代方案。
• Metal-Free and Recyclable Route to Synthesize Polysubstituted Olefins<i>via</i>CC Bond Construction from Direct Dehydrative Coupling of Alcohols or Alkenes with Alcohols Catalyzed by Sulfonic Acid-Functionalized Ionic Liquids
  作者：Feng Han、Lei Yang、Zhen Li、Yingwei Zhao、Chungu Xia

  DOI：10.1002/adsc.201301150

  日期：2014.8.11

  AbstractA direct synthesis of polysubstituted olefins via construction of CC bonds, which involves the direct dehydrative coupling of alcohols or alkenes with alcohols, was realized using a series of alkanesulfonic acid group‐functionalized ionic liquids (SO3H‐functionlization ILs) without additives. The metal‐free and recyclable catalyst system avoided the disposal and neutralization of acidic catalysts after reaction and tolerated a broad range of substrates, including benzylic, allyl, propargylic, aliphatic and aromatic or aliphatic olefins. Additionally, the catalytic system was suitable for a gram‐scale preparation. Preliminary mechanistic studies indicated that the CH bond cleavage in this reaction might be involved in the rate‐determining step.magnified image
• Iron-Catalyzed Stereospecific Olefin Synthesis by Direct Coupling of Alcohols and Alkenes with Alcohols
  作者：Zhong-Quan Liu、Yuexia Zhang、Lixing Zhao、Zejiang Li、Jiantao Wang、Huajie Li、Long-Min Wu

  DOI：10.1021/ol200372y

  日期：2011.5.6

  An efficient Fe(III)-catalyzed direct coupling of alkenes with alcohols and cross-coupling of alcohols with alcohols to give the corresponding substituted (E)-alkenes stereospecifically is demonstrated. Additionally, this reaction could be scaled up. The kinetic isotope effect (KIE) experiments indicated a typical secondary isotope effect in this process. Although benzylic alcohols were effective substrates, mild conditions, atom efficiency, environmental soundness, and stereospecificity are features that make this procedure very attractive.