((1E,4E)-1-chloropenta-1,4-diene-1,3,5-triyl)tribenzene | 1012582-51-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: ((1E,4E)-1-chloropenta-1,4-diene-1,3,5-triyl)tribenzene
• 英文别名: ((4E)-1-chloropenta-1,4-diene-1,3,5-triyl)tribenzene；(E,E)-1-chloro-1,3,5-triphenyl-1,4-pentadiene；[(1E,4E)-1-chloro-3,5-diphenylpenta-1,4-dienyl]benzene
• CAS: 1012582-51-2
• 化学式: C₂₃H₁₉Cl
• 分子量: 330.857
• InChiKey: CWIUCRZAVJCHMI-PNUIMDNNSA-N

物化性质

• 沸点：
  484.8±45.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  1,3-diphenylpropene 、 苯乙炔 在 iron(III) chloride 、 对苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 以70%的产率得到((1E,4E)-1-chloropenta-1,4-diene-1,3,5-triyl)tribenzene
  参考文献：
  名称：

  1,3-二芳基丙烯与乙炔基苯经sp 3 C-H键活化反应的铁促进合成1-Halo-1,4-pentadienes

  摘要：

  以BQ（苯醌）为氧化剂，实现了铁促进的sp 3 C-H键活化和1,3-二芳基丙烯与乙炔基苯之间的CC键形成反应。该反应在温和条件下以中等至良好的产率提供了1-卤代-1,4-戊二烯衍生物。

  DOI：

  10.1021/jo1006398

文献信息

• Boron Trihalide Mediated Alkyne-Aldehyde Coupling Reactions:  A Mechanistic Investigation
  作者：George W. Kabalka、Min-Liang Yao、Scott Borella、Zhongzhi Wu、Yu-Hong Ju、Travis Quick

  DOI：10.1021/jo702493j

  日期：2008.4.1

  A boron trihalide mediated alkyne-aldehyde coupling reaction leading to stereodefined 1,3,5-triaryl-1,5-dihalo-1,4-pentadienes is described. The study led to the discovery of a direct substitution of hydroxyl groups by stereodefined alkenyl moieties using alkenylboron dihalides. During the investigation, it was also discovered that, at low temperatures, the reaction of BCl3 with alkynes produces monovinylboron

  描述了导致立体确定的1,3,5-三芳基-1,5-二卤代-1,4-戊二烯的三卤化硼介导的炔-醛偶联反应。该研究导致发现使用烯基硼二卤化物被立体定义的烯基部分直接取代羟基的发现。在研究过程中，还发现，在低温下，BCl 3与炔烃的反应生成的是单乙烯基硼二氯化物，而不是所报道的二乙烯基硼氯化物。现在提出了改进的三氯化硼介导的炔-醛偶联反应的反应机理。已经发现反应温度和添加方式对二烯产物的立体化学有显着影响。
• Fe powder catalyzed highly efficient synthesis of alkenyl halides via direct coupling of alcohols and alkynes with aqueous HX as exogenous halide sources
  作者：Yong-Rong Yang、Qiang Zhang、Feng-Tian Du、Jian-Xin Ji

  DOI：10.1016/j.tet.2015.04.065

  日期：2015.6

  A simple and efficient catalytic method for the synthesis of alkenyl halides via direct coupling of alcohols and alkynes using aqueous HX (X=Cl, Br) as halide sources has been developed under mild conditions in the presence of Fe powder (1 mol %). In comparison with the high loading of FeX3 in previously reported protocols, the present approach provides a remarkable attractive methodology to a diverse

  已经在温和的条件下，在铁粉（1摩尔％）存在的条件下，开发了一种简单高效的催化方法，该方法通过使用HX水溶液（X = Cl，Br）作为卤化物源，通过醇和炔烃的直接偶联来合成烯基卤化物。与以前报道的方案中FeX 3的高负载相比，由于操作简单和金属污染程度低的优点，本方法为各种范围的烯基卤化物提供了引人注目的有吸引力的方法。
• New and Efficient Iron Halide Mediated Synthesis of Alkenyl Halides through Coupling of Alkynes and Alcohols
  作者：Srijit Biswas、Sukhendu Maiti、Umasish Jana

  DOI：10.1002/ejoc.200900104

  日期：2009.5

  simple, and straightforward one-pot reaction of alkynes with various alcohols in the presence of iron salts (FeCl3 and FeBr3) was described to yield the corresponding alkenyl halides with complete regioselectivity and highstereoselectivity. The reaction is high yielding and works under mild conditions. The iron salts act as Lewis acids and a source of halides. The reaction tolerates a wide variety of functional

  在铁盐（FeCl3 和 FeBr3）的存在下，炔烃与各种醇的新颖、简单和直接的一锅反应被描述为产生具有完全区域选择性和高立体选择性的相应烯基卤化物。该反应收率高，反应条件温和。铁盐充当路易斯酸和卤化物源。该反应耐受多种官能团。值得注意的是，这种方法便宜、高效且环保。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Titanium(IV) Halide Mediated Coupling of Alkoxides and Alkynes: An Efficient and Stereoselective Route to Trisubstituted (<i>E</i>)-Alkenyl Halides
  作者：Min-Liang Yao、Travis R. Quick、Zhongzhi Wu、Michael P. Quinn、George W. Kabalka

  DOI：10.1021/ol900669t

  日期：2009.6.18

  Alkoxide C-O bond cleavage occurs readily at room temperature in the presence of titanium(IV) halide. Capture of the resultant carbocation by alkynes provides an efficient route to trisubstituted (E)-alkenyl halides with high stereoselectivity.
• Iron-Promoted Synthesis of Substituted 1-Halo-1,4-pentadienes by Reaction of 1,3-Diarylpropenes with Ethynylbenzenes via sp³ C−H Bond Activation
  作者：Hanjie Mo、Weiliang Bao

  DOI：10.1021/jo1006398

  日期：2010.7.16

  An iron-promoted sp3 C−H bond activation and C−C bond formation reaction between 1,3-diarylpropenes and ethynylbenzenes was realized with BQ (benzoquinone) as an oxidant. The reaction afforded 1-halo-1,4-pentadiene derivatives in moderate to good yields under mild conditions.

  以BQ（苯醌）为氧化剂，实现了铁促进的sp 3 C-H键活化和1,3-二芳基丙烯与乙炔基苯之间的CC键形成反应。该反应在温和条件下以中等至良好的产率提供了1-卤代-1,4-戊二烯衍生物。