(E)-(3-(4-chlorophenyl)prop-2-ene-1,1-diyl)dibenzene | 1104997-38-7

• 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-2-ene-1,1-diyl)dibenzene
• 英文别名: 1-chloro-4-[(E)-3,3-diphenylprop-1-enyl]benzene
• CAS: 1104997-38-7
• 化学式: C₂₁H₁₇Cl
• 分子量: 304.819
• InChiKey: DWTSRHBHFMJAMA-DTQAZKPQSA-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

• 作为反应物：
  描述：

  (E)-(3-(4-chlorophenyl)prop-2-ene-1,1-diyl)dibenzene 在 亚硝酸特丁酯 、 氧气 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以75%的产率得到1-(4-chlorophenyl)-2-nitro-3,3-diphenylpropyl nitrate
  参考文献：
  名称：

  亚硝酸叔丁酯介导内部烯烃的硝化

  摘要：

  在氧气气氛中，亚硝酸叔丁酯（TBN）与不对称的内部苄基烯烃反应，生成硝基硝化反应产物，而α，β-不饱和羧酸则生成硝基链烯。在两种情况下，即使其他自由基共存于介质中，NO 2基团也仅攻击β碳。

  DOI：

  10.1002/ejoc.202000149
• 作为产物：
  描述：

  4-氯苯乙烯 、 二苯甲醇 在 三氟甲磺酸 作用下， 以 1,2-二溴乙烷 为溶剂， 以99%的产率得到(E)-(3-(4-chlorophenyl)prop-2-ene-1,1-diyl)dibenzene
  参考文献：
  名称：

  SP 3 - SP 2 CC键的形成通过醇和烯的质子酸三氟甲磺酸催化直接偶联

  摘要：

  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。

  DOI：

  10.1002/adsc.201100262

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。
• Copper(I) Catalyzed Differential Peroxidation of Terminal and Internal Alkenes Using TBHP
  作者：Bilal Ahmad Mir、Suresh Rajamanickam、Pakiza Begum、Bhisma K. Patel

  DOI：10.1002/ejoc.201901689

  日期：2020.1.16

  A TBHP mediated carbonylation–peroxidation of styrene, α‐peroxidation of α‐substituted unsymmetrical internal alkenes and concurrent peroxidation–carbonylation–cycloalkylation/cycloetherifiction of internal cyclic alkene (indene) have been developed.

  已经开发出TBHP介导的苯乙烯的羰基化-过氧化，α-取代的不对称内部烯烃的α-过氧化以及内部环状烯烃（茚）的同时过氧化-羰基化-环烷基化/环醚化。
• Ionic Liquid‐Catalyzed C−C Bond Formation for the Synthesis of Polysubstituted Olefins
  作者：Haotian Lv、Feng Han、Ning Wang、Nan Lu、Zenghong Song、Jian Zhang、Chengxia Miao

  DOI：10.1002/ejoc.202201222

  日期：2022.12.6

  Acidic ionic liquid was used as a metal-free and recyclable catalyst for the synthesis of polysubstituted olefins by activating of ethers in dimethyl carbonate as a green solvent. Density functional theory (DFT) calculations showed a hydrogen bonding effect during the reaction.

  酸性离子液体被用作无金属和可回收催化剂，通过在碳酸二甲酯作为绿色溶剂中活化醚来合成多取代烯烃。密度泛函理论 (DFT) 计算表明在反应过程中存在氢键效应。
• 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.