(E)-3-cyclohexyl-2-methyl-1-phenylprop-2-en-1-one | 67615-43-4

• 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)-3-cyclohexyl-2-methyl-1-phenylprop-2-en-1-one
• CAS: 67615-43-4
• 化学式: C₁₆H₂₀O
• 分子量: 228.334
• InChiKey: VVXXUVBOCSGNPH-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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 、 环己烷基甲醛 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以65%的产率得到(E)-3-cyclohexyl-2-methyl-1-phenylprop-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

• Indium(III)-catalyzed Coupling between Alkynes and Aldehydes to α,β-Unsaturated Ketones
  作者：Katsukiyo Miura、Kiyomi Yamamoto、Aya Yamanobe、Keisuke Ito、Hidenori Kinoshita、Junji Ichikawa、Akira Hosomi

  DOI：10.1246/cl.2010.766

  日期：2010.7.5

  The combined use of a catalytic amount of InX3 (X = OTf and NTf2) and 1-butanol was found to be effective in formal alkyne–aldehyde metathesis. With this catalytic system, aromatic alkynes reacted with aromatic aldehydes to give chalcones in moderate to good yields. Alkynals were efficiently converted into 5- to 7-membered cyclic compounds by intramolecular alkyne–aldehyde coupling.

  研究发现，InX3（X = OTf 和 NTf2）与1-丁醇联合使用在形式炔烃-醛交叉偶联反应中具有很好的效果。在该催化体系下，芳香炔烃与芳香醛反应生成查尔酮，产率中等至良好。炔醛通过分子内炔烃-醛偶联高效转化为5至7元环状化合物。
• Palladium-catalyzed formal hydroacylation of allenes employing carboxylic anhydrides and hydrosilanes
  作者：Tetsuaki Fujihara、Takuro Hosomi、Cong Cong、Tomoya Hosoki、Jun Terao、Yasushi Tsuji

  DOI：10.1016/j.tet.2015.01.066

  日期：2015.7

  The formal hydroacylation reaction of allenes has been developed employing carboxylic anhydrides as acyl sources and hydrosilanes as reducing reagents in the presence of a commercially available palladium complex as a catalyst. The reaction affords α,β-unsaturated ketones regio- and stereoselectively. The similar catalyst system is also effective for the reduction of carboxylic anhydrides to the corresponding

  在市售的钯配合物作为催化剂的存在下，已经开发了使用羧酸酐作为酰基源和氢化硅烷作为还原剂的丙二烯的正式加氢酰化反应。该反应区域和立体选择性地提供α，β-不饱和酮。相似的催化剂体系对于使用氢化硅烷将羧酸酐还原为相应的醛也是有效的。
• 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.
• Palladium-Catalyzed Formal Hydroacylation of Allenes Employing Acid Chlorides and Hydrosilanes
  作者：Tetsuaki Fujihara、Kenta Tatsumi、Jun Terao、Yasushi Tsuji

  DOI：10.1021/ol400862k

  日期：2013.5.3

  The palladium-catalyzed formal hydroacylation of allenes employing acid chlorides and hydrosilanes has been achieved. The reactions proceed with commercially available Pd(OAc)(2) as a catalyst and HSi(iPr)(3) as a reducing reagent, giving the corresponding alpha,beta-unsaturated ketones regio- and stereoselectively.
• 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。