(E)-2,5-dimethyl-1-phenylhex-2-en-1-one

• 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: (E)-2,5-dimethyl-1-phenylhex-2-en-1-one
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: GZYVEZIBEBPNOS-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-1-丙炔 、 异戊醛 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以80%的产率得到(E)-2,5-dimethyl-1-phenylhex-2-en-1-one
  参考文献：
  名称：

  Fe（III）卤化物作为碳-碳键形成中的有效催化剂：1,5-二卤代-1,4-二烯，α，β-不饱和酮和环醚的合成

  摘要：

  卤化铁（III）被证明是乙炔和醛偶联的极好催化剂。当使用末端乙炔时，获得的主要产物是1,5-二卤代1,4,4-二烯，其中（E，Z）-立体化学在某些情况下被（E）-α，β-不饱和酮污染。当使用非末端芳烃时，前者的羰基衍生物是唯一分离出的产物。当使用高炔丙醇时，发生Prins型环化反应，生成2-烷基-4-卤代-5,6-二氢-2 H-pyrans。另外，无水卤化铁也被证明是用均烯丙基醇进行标准Prins环化的极佳催化剂。中间缩醛的分离，计算和炔烃水合研究为提出的机理提供了依据。

  DOI：

  10.1021/jo048410j

文献信息

• Fe(III) Halides as Effective Catalysts in Carbon−Carbon Bond Formation:  Synthesis of 1,5-Dihalo-1,4-dienes, α,β-Unsaturated Ketones, and Cyclic Ethers
  作者：Pedro O. Miranda、David D. Díaz、Juan I. Padrón、Miguel A. Ramírez、Víctor S. Martín

  DOI：10.1021/jo048410j

  日期：2005.1.1

  homopropargylic alcohols were used, a Prins-type cyclization occurred yielding 2-alkyl-4-halo-5,6-dihydro-2H-pyrans. In addition, anhydrous ferric halides are also shown to be excellent catalysts for the standard Prins cyclization with homoallylic alcohols. Isolation of an intermediate acetal, calculations, and alkyne hydration studies provide substantiation of a proposed mechanism.

  卤化铁（III）被证明是乙炔和醛偶联的极好催化剂。当使用末端乙炔时，获得的主要产物是1,5-二卤代1,4,4-二烯，其中（E，Z）-立体化学在某些情况下被（E）-α，β-不饱和酮污染。当使用非末端芳烃时，前者的羰基衍生物是唯一分离出的产物。当使用高炔丙醇时，发生Prins型环化反应，生成2-烷基-4-卤代-5,6-二氢-2 H-pyrans。另外，无水卤化铁也被证明是用均烯丙基醇进行标准Prins环化的极佳催化剂。中间缩醛的分离，计算和炔烃水合研究为提出的机理提供了依据。
• β′-Hydroxy-α,β-unsaturated ketones: A new pharmacophore for the design of anticancer drugs
  作者：José M. Padrón、Pedro O. Miranda、Juan I. Padrón、Víctor S. Martín

  DOI：10.1016/j.bmcl.2006.01.023

  日期：2006.4

  A series of beta'-hydroxy-alpha,beta-unsaturated ketones were prepared by means of an iron(III) catalyzed domino process. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, SW1573, and WiDr. The results showed that beta'-hydroxy-alpha,beta-unsaturated ketones were more potent than alpha,beta-unsaturated ketones. The best activity profiles were obtained for the derivatives bearing cyclic or branched substituents on the side chains. (C) 2006 Elsevier Ltd. All rights reserved.
• Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents:  Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF₃, and HBF₄
  作者：Jong Uk Rhee、Michael J. Krische

  DOI：10.1021/ol050838x

  日期：2005.6.1

  The first use of cationic silver (AgSbF4) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4) and Lewis acid (BF3) catalyst systems is made. Notably, intermolecular coupling proceeds stereoselectively to afford the corresponding trisubstituted enones as single geometrical isomers. This transformation represents a completely atom economical alternative to the use of stabilized Wittig reagents in carbonyl olefination and may be viewed as a formal alkyne-carbonyl metathesis.
• Barluenga's reagent with HBF₄as an efficient catalyst for alkyne-carbonyl metathesis of unactivated alkynes
  作者：Kosuke Murai、Keiichiro Tateishi、Akio Saito

  DOI：10.1039/c6ob02090a

  日期：——

  Barluenga's reagent (IPy2BF4, Py = pyridine) treated with HBF4 efficiently catalyzes the inter- and intramolecular alkyne-carbonyl metathesis of unactivated alkynes with aldehydes or ketones, most of which proceed at room temperature. This work represents the first catalytic application of the Barluenga's reagent.

  用HBF 4处理的Barluenga试剂（IPy 2 BF 4，Py =吡啶）可有效催化未活化炔烃与醛或酮的分子间和分子内炔烃羰基复分解反应，其中大部分在室温下进行。这项工作代表了Barluenga试剂的首次催化应用。