1,4-diphenyl-but-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: 1,4-diphenyl-but-2-en-1-one
• 英文别名: 1,4-Diphenylbut-2-en-1-one
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: PUSJUCUWYXEGSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-diphenyl-but-2-en-1-one 在 potassium carbonate 、 对甲苯磺酰肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以51%的产率得到1,4-联苯基-1-丁酮
  参考文献：
  名称：

  以甲苯磺酰肼为氢源的无过渡金属的新型无过渡金属共轭还原的α，β-不饱和酮

  摘要：

  已开发出一种新颖有效的方法，以甲苯磺酰肼为氢源，将α，β-不饱和酮化学选择性共轭还原为相应的饱和酮，产率中等至良好。本协议不需要使用过渡金属，并且有效地适用于广泛的衬底（25个示例）。

  DOI：

  10.1016/j.tetlet.2014.07.063
• 作为产物：
  描述：

  (E)-β-chlorostyrene 在 iron(II) chloride 频哪酮 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.17h， 生成 1,4-diphenyl-but-2-en-1-one
  参考文献：
  名称：

  Competition of Mechanisms in Nucleophilic Substitution of Vinyl Halides. An Unequivocal Example of the Vinylic SRN1 Route1

  摘要：

  In a search for an unambiguous example of the vinylic S(RN)1 route, several vinyl bromides and iodides were reacted mostly with (-)CH(2)COCMe(3), and sometimes with (-)CH(2)COPh, (CH)-C--(Me)COEt, and (EtO)(2)PO- ions, under Fe2+- or photostimulation in Me(2)SO. Vinyl halides having vinylic hydrogens, such as beta-bromostyrene, gave acetylenic products, e.g., phenylacetylene or a tertiary PhC=C-substituted alcohol, whereas vinyl halides with allylic hydrogens, such as Me(2)C=C(I)CHMe(2), gave a substituted allene. Reduction products of the halogen, as well as substitution and rearranged substitution products, were also formed. The operation of ionic elimination-addition routes accounts for formation of most of the products, while the reduction products arise from an intermediate vinyl radical. Ph(2)C=C(Br)Ph (20) and Me(2)C=C(Br)Ph (25) gave both substitution and reduction products, but Me(2)C=C(Br)-t-Bu (23) gave only a reduction product. Formation of substitution products from the conjugated 20 and 25 was ascribed to a reaction via a vinylic S(RN)1 route, while lack of substitution in 23 is related to its nonconjugated system and to the consequent higher energy that the radical anion of the substitution product would have. The one here reported seems to be the first case of an exclusive genuine vinylic S(RN)1 process.

  DOI：

  10.1021/jo00101a045

文献信息

• Novel sequential 1,4-Brook rearrangement–Wittig reaction: new one-pot approach for silyl dienol ethers
  作者：Yuji Matsuya、Azusa Koiwai、Daishiro Minato、Kenji Sugimoto、Naoki Toyooka

  DOI：10.1016/j.tetlet.2012.08.114

  日期：2012.10

  method of silyl dienol ethers via 1,4-Brook rearrangement–Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.

  已开发出一种通过1,4-Brook重排-Wittig反应序列合成甲硅烷基二烯醇醚的新型一锅法。该串联反应通过分子内甲硅烷基迁移步骤进行，该步骤使得能够立体选择性地形成膦烷中间体。该反应操作简单且产率高，因此为甲硅烷基二烯醇醚的合成提供了新的有用的配方。
• [EN] A METHOD FOR PREPARING SULFUR-CONTAINING COMPOUNDS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS CONTENANT DU SOUFRE
  申请人：ROYAL COLLEGE OF SURGEONS IE

  公开号：WO2010066450A1

  公开（公告）日：2010-06-17

  The invention provides a method for preparing sulfur-containing compounds, the method comprising reacting a donor compound comprising at least one sulfur having at least one lone pair of electrons, with an acceptor compound; wherein the reaction occurs in the presence of an amine, optionally an amine catalyst, capable of activating the sulfur having at least one lone pair of electrons; and wherein the reaction occurs via the formation of an transient intermediate species, optionally a transient intermediate species, between the amine, optionally the amine catalyst and the donor compound; and wherein the donor compound is selected from the group consisting of a sulfurous acid, a sulfenic acid and a sulfinic acid or a salt, ester or amide of a sulfurous acid, a sulfenic acid and a sulfinic acid. The invention also provides sulfur-containing compounds of the formula: wherein R is selected from: (a) 1 -(4-Nitro-phenyl)-3-oxo-3-phenyl-propane; (b) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1 -phenyl-ethane; (c) 1-(4-Methoxy-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (d) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1-(4-nitro-phenyl)-ethane; (e) 1-(4-Fluoro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (f) 1 -(4-Chloro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; and (g) 3-Oxo-cyclohexane. Finally, the invention provides use of chiral sulfur-containing compounds obtainable by the above-mentioned method or chiral sulfur-containing compounds as mentioned above for the resolution of racemic mixtures of amines.

  该发明提供了一种制备含硫化合物的方法，该方法包括将包含至少一个硫原子且至少一个孤对电子的给体化合物与受体化合物反应；其中，在胺的存在下进行反应，可选地，在能够激活至少一个硫原子具有至少一个孤对电子的胺的存在下进行反应；反应通过形成瞬态中间体物种进行，可选地，通过胺、可选地胺催化剂和给体化合物之间的瞬态中间体物种进行反应；给体化合物选自包括亚硫酸、亚硫酸和亚砜酸或亚硫酸、亚硫酸和亚砜酸的盐、酯或酰胺的群；该发明还提供了符合以下公式的含硫化合物：其中R选自：(a) 1-(4-硝基苯基)-3-氧代-3-苯基-丙烷；(b) 2-(3-甲基-4-硝基异噁唑-5-基)-1-苯基-乙烷；(c) 1-(4-甲氧基苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(d) 2-(3-甲基-4-硝基异噁唑-5-基)-1-(4-硝基苯基)-乙烷；(e) 1-(4-氟苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(f) 1-(4-氯苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；和(g) 3-氧代环己烷。最后，该发明提供了通过上述方法获得的手性含硫化合物或上述提到的手性含硫化合物用于分离胺的外消旋混合物。
• Preparation of a Bi2WO6 catalyst and its catalytic performance in an alpha alkylation reaction under visible light irradiation
  作者：Xiaoling Liu、Haiying Li、Jingjing Ma、Xiujuan Yu、Yan Wang、Jingyi Li

  DOI：10.1016/j.mcat.2019.01.018

  日期：2019.4

  valence states of the catalysts. Then, the catalysts were used to catalyze the alpha alkylation reaction of benzyl alcohol and acetophenone to obtain 1,3-diphenyl-1-propenone under visible light irradiation, and the photocatalytic reaction conditions were optimized. To expand the applicable range of alpha alkylation, the influence of different alcohols and different ketone derivatives on the photocatalytic

  在这项研究中，使用Bi（NO 3）3 •5H 2 O和Na 2 WO 4 •2H 2通过水热法合成了不同类型的Bi 2 WO 6催化剂。以O为前体，以及各种表征方法，例如X射线衍射（XRD），X射线光电子能谱（XPS），扫描电子显微镜（SEM），透射电子显微镜（TEM），紫外-可见漫反射光谱（UV） –vis DRS），Brunauer-Emmett-Teller（BET）比表面积测量和光致发光（PL）分析，用于表征催化剂的形态，结构和价态。然后，在可见光照射下，用该催化剂催化苯甲醇与苯乙酮的α烷基化反应，得到1，3-二苯基-1-丙烯酮，并优化了光催化反应条件。为了扩大α烷基化的适用范围，确定了不同的醇和不同的酮衍生物对光催化反应的影响。Ò 2 - ），空穴（h +）和电子（e -的反应过程中产生的））进行了测试。
• Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N-Heterocyclic-Carbene/Thiourea/Tertiary-Amine Multicatalysis
  作者：Zhichao Jin、Jianfeng Xu、Song Yang、Bao-An Song、Yonggui Robin Chi

  DOI：10.1002/anie.201305023

  日期：2013.11.18

  make light work: In an organocatalytic asymmetric sulfonation of enones, the activation of a sulfonyl imine by an N‐heterocyclic carbene (NHC) catalyst led to the release of a sulfinic anion, which underwent nucleophilic addition to the enone. The enantioselectivity of the process was controlled by a chiral thiourea/amine co‐catalyst through anion recognition and hydrogen‐bonding interactions. Tol=p‐tolyl

  许多手轻而易举：在烯酮的有机催化不对称磺化中，N-杂环卡宾（NHC）催化剂对磺酰基亚胺的活化导致亚砜阴离子的释放，该亚砜阴离子经过亲核加成后成为烯酮。该过程的对映选择性是通过手性硫脲/胺助催化剂通过阴离子识别和氢键相互作用来控制的。Tol = p-甲苯基。
• Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst
  作者：Liang Li、Yidong Liu、Yang Peng、Lei Yu、Xiaoyan Wu、Hailong Yan

  DOI：10.1002/anie.201508127

  日期：2016.1.4

  Reported herein is the first enantioselective β‐elimination reaction catalyzed by a chiral cation‐binding polyether. By using this catalytic protocol, a wide range of β‐sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate

  本文报道的是手性阳离子结合聚醚催化的第一个对映选择性β-消除反应。通过使用这种催化方案，可以以高的立体选择性（S高达> 300）有效地分离各种β-磺酰基酮。该方法成功的关键是催化剂与砜基质上的路易斯碱性基团之间有利的二次相互作用。该方法的烯酮产物可轻松转化为外消旋原料，并可以高收率和出色的对映选择性有效地循环利用和全面合成手性β-磺酰基酮。