(E)-(3-(4-chlorophenyl)prop-1-ene-1,3-diyl)dibenzene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-(3-(4-chlorophenyl)prop-1-ene-1,3-diyl)dibenzene
• 英文别名: (E)-[3-(4-chlorophenyl)prop-1-ene-1,3-diyl]dibenzene；rac-(E)-1,3-diphenyl-3-(4-chlorophenyl)prop-1-ene；1-chloro-4-[(E)-1,3-diphenylprop-2-enyl]benzene
• 化学式: C₂₁H₁₇Cl
• 分子量: 304.819
• InChiKey: YCDPQRKWQNSVGY-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• 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：

  苏合香醇 、 4-氯二苯甲醇 在 iron(III) chloride hexahydrate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 以59%的产率得到(E)-(3-(4-chlorophenyl)prop-1-ene-1,3-diyl)dibenzene
  参考文献：
  名称：

  Iron-Catalyzed Stereospecific Olefin Synthesis by Direct Coupling of Alcohols and Alkenes with Alcohols

  摘要：

  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.

  DOI：

  10.1021/ol200372y

文献信息

• Direct coupling of alcohols with alkenylsilanes catalyzed by indium trichloride or bismuth tribromide
  作者：Yoshihiro Nishimoto、Masayuki Kajioka、Takahiro Saito、Makoto Yasuda、Akio Baba

  DOI：10.1039/b816072d

  日期：——

  Indium halides or bismuth halides catalyzed the coupling of various alcohols with alkenylsilanes to give the corresponding alkenes stereospecifically without any other activators.

  铟或铋的卤化物催化各种醇与烯丙基硅烷的偶联反应，立体选择性地生成相应的烯烃，过程中无需其他活化剂。
• sp3-sp2 C-C Bond Formation via Brønsted Acid Trifluoromethanesulfonic Acid-Catalyzed Direct Coupling Reaction of Alcohols and Alkenes
  作者：Hui-Lan Yue、Wei Wei、Ming-Ming Li、Yong-Rong Yang、Jian-Xin Ji

  DOI：10.1002/adsc.201100262

  日期：2011.11

  A novel and efficient trifluoromethanesulfonic acid-catalyzed sp3-sp2 CC bond formation reaction through the direct coupling of alcohols with alkenes has been realized under mild conditions. The present protocol provides an attractive approach to a diverse range of polysubstituted olefins in good to excellent yields with high stereo- and regioselectivities.

  一种新颖的和有效的三氟甲磺酸催化的SP 3 - SP 2 CC键形成通过醇与链烯烃的直接偶联反应已经温和的条件下实现的。本方案提供了一种吸引人的方法，可用于多种多样的多取代烯烃，具有良好的收率和优异的收率，并具有较高的立体选择性和区域选择性。
• 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.
• Microwave-assisted arylation of rac-(E)-3-acetoxy-1,3-diphenylprop-1-ene with arylboronic acids
  作者：Viera Poláčková、Štefan Toma、C. Oliver Kappe

  DOI：10.1016/j.tet.2007.06.045

  日期：2007.9

  The palladium-catalyzed arylation of rac-(E)-3-acetoxy-1,3-diphenylprop-1-ene with arylboronic acids was studied under controlled microwave irradiation conditions. A variety of different catalysts, bases, and solvents were explored in order to achieve optimum yields in the shortest possible reaction times. The best isolated yields were obtained using Pd-2(dba)(3)center dot CHCl3/PPh3 as the catalytic system, potassium phosphate monohydrate as the base, and toluene/H2O as a solvent system. Microwave irradiation using 5 mol% of the palladium catalyst for 90 s (max. temp 170 degrees C) generally afforded the cross-coupling products in good to excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.
• 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