(E)-5-styryl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene | 1286741-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: (E)-5-styryl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene
• 英文别名: (E)-5-styryl-10,11-dihydro-5H-dibenzo[a,d][7]annulene
• CAS: 1286741-52-3
• 化学式: C₂₃H₂₀
• 分子量: 296.412
• InChiKey: GJCZAQKFFXOMPF-SAPNQHFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  苯乙烯 、 二苯并噻唑 在 N-octadecyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到(E)-5-styryl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene
  参考文献：
  名称：

  通过磺酸或功能化离子液体催化的醇或烯烃与醇的直接脱水偶联，通过CC键构建无金属且可循环利用的途径来合成多取代的烯烃

  摘要：

  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

  DOI：

  10.1002/adsc.201301150

文献信息

• 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.