(6,6-dimethyl-3,4-heptadienyl)benzene | 67647-98-7

• 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: (6,6-dimethyl-3,4-heptadienyl)benzene
• 英文别名: (6,6-dimethylhepta-3,4-dienyl)benzene；2,2-Dimethyl-5-phenyl-3,4-heptadien
• CAS: 67647-98-7
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: IQCVXYALQRWIOV-UHFFFAOYSA-N

物化性质

• 沸点：
  276.5±10.0 °C(Predicted)
• 密度：
  0.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  diisopropyl (E)-1-(1-hydroxy-3-phenylpropyl)-3,3-dimethyl-1-butenylphosphonate 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以79%的产率得到(6,6-dimethyl-3,4-heptadienyl)benzene
  参考文献：
  名称：

  烯基膦酸酯通过 Horner-Wadsworth-Emmons 烯烃的烯化

  摘要：

  单取代和双取代的丙二烯 5 是通过从亚甲基双膦酸酯 1 和两个羰基化合物开始的连续霍纳-沃兹沃思-埃蒙斯烯化合成的。成功的关键是 KH 或 KH-18-crown-6 作为羟基烯基膦酸酯 4 的第二次 HWE 烯化的基础。

  DOI：

  10.1080/10426500212268

文献信息

• C(sp)–C(sp³) Bond Formation through Cu-Catalyzed Cross-Coupling of<i>N</i>-Tosylhydrazones and Trialkylsilylethynes
  作者：Fei Ye、Xiaoshen Ma、Qing Xiao、Huan Li、Yan Zhang、Jianbo Wang

  DOI：10.1021/ja3004792

  日期：2012.4.4

  Copper-catalyzed cross-coupling of N-tosylhydrazones with trialkylsilylethynes leads to the formation of C(sp)-C(sp(3)) bonds. Cu carbene migratory insertion is proposed to play the key role in this transformation.

  N-甲苯磺酰腙与三烷基甲硅烷基乙炔的铜催化交叉偶联导致形成 C(sp)-C(sp(3)) 键。提出Cu卡宾迁移插入在这种转变中起关键作用。
• The synthesis of allenes by Cu(i)-catalyzed regio- and stereoselective reduction of propargylic carbonates with hydrosilanes
  作者：Chongmin Zhong、Yusuke Sasaki、Hajime Ito、Masaya Sawamura

  DOI：10.1039/b910192f

  日期：——

  Cu(I)-catalyzed anti-SN2′-type reduction of internal propargylic carbonates with hydrosilanes affords various di- and trisubstituted allenes with high regioselectivities; the reactions are compatible with functional groups and work efficiently for the synthesis of optically-active allenes.

  铜(I)催化的反SN2'型内丙炔碳酸酯与氢硅烷的还原反应可以高选择性地产生多种二取代和三取代的烯烃；该反应与功能基团兼容，并且在合成光学活性烯烃方面表现出高效性。
• CuI-Catalyzed Cross-Coupling of <i>N</i>-Tosylhydrazones with Terminal Alkynes: Synthesis of 1,3-Disubstituted Allenes
  作者：Mohammad Lokman Hossain、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo3024686

  日期：2013.2.1

  A CuI-catalyzed synthesis of 1,3-disubstituted allenes from 1-alkynes by the reaction with various N-tosylhydrazones has been developed. This method, which uses readily available starting materials and is operationally simple, offers 1,3-disubstituted allenes in moderate to good yields. The reaction also tolerates various functional groups.

  通过与各种N-甲苯磺酰hydr的反应，由CuI催化从1-炔烃中合成1，3-二取代的烯丙基。该方法使用容易获得的起始原料并且操作简单，以中等至良好的产率提供了1，3-二取代的烯。该反应还容许各种官能团。
• A CONVENIENT METHOD FOR THE PREPARATION OF ALLENES FROM PROPARGYL ALCOHOLS USING 1-ETHYL-2-FLUORO-4,6-DIMETHYLPYRIDINIUM TETRAFLUOROBORATE
  作者：Teruaki Mukaiyama、Ken Kawata

  DOI：10.1246/cl.1978.785

  日期：1978.7.5

  In the presence of a catalytic amount of copper(I) iodide, Grignard reagents reacted with 2-propargyloxypyridinium salts, formed in situ from propargyl alcohols and 1-ethyl-2-fluoro-4,6-dimethylpyridinium tetrafluoroborate, to produce various substituted allenes in good yields.

  在一定量的碘化铜催化下，格氏试剂与由丙炔醇和 1-乙基-2-氟-4,6-二甲基吡啶鎓四氟硼酸盐就地生成的 2-丙炔氧基吡啶鎓盐发生反应，以良好的产率生成各种取代的烯烃。
• SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction
  作者：Abdallah B. Diagne、Shuheng Li、Gregory A. Perkowski、Milan Mrksich、Regan J. Thomson

  DOI：10.1021/acscombsci.5b00131

  日期：2015.11.9

  Development of the self-assembled monolayer/MALDI mass spectrometry (SAMDI) platform to enable a high-throughput optimization of a traceless Petasis reaction is described. More than 1800 unique reactions were conducted simultaneously on an array of self-assembled monolayers of alkanethiolates on gold to arrive at optimized conditions, which were then successfully transferred to the solution phase. The utility of this reaction was validated by the efficient synthesis of a variety of di- and trisubstituted allenes.