2,4-dichlorophenyl vinyl ketone | 63198-77-6

• 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: 2,4-dichlorophenyl vinyl ketone
• 英文别名: 1-(2,4-dichlorophenyl)propenone；1-(2,4-dichlorophenyl)prop-2-en-1-one
• CAS: 63198-77-6
• 化学式: C₉H₆Cl₂O
• 分子量: 201.052
• InChiKey: GHMVIYIMUFPEHN-UHFFFAOYSA-N

物化性质

• 沸点：
  297.8±40.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,4-dichlorophenyl vinyl ketone 、 辅酶 A 以 水 为溶剂， 反应 2.0h， 生成 3-CoA-1-(2,4-dichlorophenyl)propan-1-one
  参考文献：
  名称：

  CoA Adducts of 4-Oxo-4-phenylbut-2-enoates: Inhibitors of MenB from the M. tuberculosis Menaquinone Biosynthesis Pathway

  摘要：

  A high-throughput screen led to the discovery of 2-amino-4-oxo-4-phenylbutanoate inhibitors of the 1,4-dihydroxy-2-naphthoyl-CoA synthase (MenB) from the menaquinone biosynthesis pathway in Mycobacterium tuberculosis. However, these compounds are unstable in solution and eliminate to form the corresponding 4-oxo-4-phenylbut-2-enoates that then react with CoA in situ to form nanomolar inhibitors of MenB. The potency of these compounds results from interaction of the CoA adduct carboxylate with the MenB oxyanion hole, a conserved structural motif in the crotonase superfamily. 4-Oxo-4-chlorophenylbutenoyl methyl ester has minimum inhibitory concentrations of 0.6 and 1.5 mu g/mL against replicating and nonreplicating M. tuberculosis, respectively, and it is proposed that the methyl ester penetrates the cell where it is hydrolyzed and reacts with CoA to generate the active antibacterial. The CoA adducts thus represent an important foundation for the development of novel MenB inhibitors and suggest a general approach to the development of potent inhibitors of acyl-CoA binding enzymes.

  DOI：

  10.1021/ml200141e
• 作为产物：
  描述：

  β-Dimethylamino-2,4-dichlorophenylpropiophenone hydrochloride 在 N,N-二异丙基乙胺 作用下， 以77 %的产率得到2,4-dichlorophenyl vinyl ketone
  参考文献：
  名称：

  芳基乙烯基酮的高效合成方法及其在含羞草醇的 DFT 和自动对接研究中的合成应用

  摘要：

  使用低成本且市售的氯甲酸乙酯和二异丙基乙胺作为试剂，开发了一种高效且优雅的方法来制备取代的苯基乙烯基酮。该方法还应用于含羞草醇和喹啉等天然产物的合成。对含羞草醇进行前沿分子轨道（FMO）研究，以了解其化学反应性。电子定位函数（ELF）和局域轨道定位器（LOL）分析提供了有关局域和离域电子的信息。降低密度梯度 (RDG) 分析提供了空间、范德华和氢键相互作用的信息。分子静电势 (MEP) 和 Fukui 函数提供了有关亲核和亲电攻击的信息。非线性光学（NLO）分析代表了含羞草醇良好的 NLO 材料。分子对接表明含羞草醇化合物能有效抑制aspulvinone二甲基烯丙基转移酶。

  DOI：

  10.3390/molecules28176214

文献信息

• SUBSTITUTED 7-SULFANYLMETHYL-, 7-SULFINYLMETHYL- AND 7-SULFONYLMETHYLINDOLES AND THE USE THEREOF
  申请人：Kolkhof Peter

  公开号：US20100105744A1

  公开（公告）日：2010-04-29

  The present application relates to novel 7-sulfanylmethyl-, 7-sulfinylmethyl- and 7-sulfonylmethylindole derivatives, processes for the preparation thereof, the use thereof alone or in combinations for the treatment and/or prevention of diseases, and the use thereof for the manufacture of medicaments for the treatment and/or prevention of diseases, especially for the treatment and/or prevention of cardiovascular disorders.

  本申请涉及新颖的7-硫代甲基、7-亚砜基甲基和7-磺酰基甲基吲哚衍生物，其制备方法，单独或组合使用以治疗和/或预防疾病，以及用于制造用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病。
• A novel metal-free synthesis of thiazole-substituted α-hydroxy carbonyl compounds and 2-alkenylthiazoles from thiazole N-oxides and olefins
  作者：Hui Li、Juan Zhang、Yanqiu Zhang、Jiayi Wang、Gonghua Song

  DOI：10.1016/j.tetlet.2019.05.053

  日期：2019.12

  A metal-free and highly atom-economic synthesis of thiazole-substituted α-hydroxy carbonyl compounds has been developed. Catalyzed by 5 mol% of p-toluenesulfonic acid (TsOH), a variety of thiazole-substituted α-hydroxy carbonyl compounds were obtained in moderate to good yields via 1,3-dipolar cycloaddition of thiazole N-oxides with olefins, followed by a ring-opening reaction. Furthermore, the corresponding

  已经开发了无金属且高度原子经济的噻唑取代的α-羟基羰基化合物的合成方法。在5摩尔％的对甲苯磺酸（TsOH）的催化下，通过噻唑N-氧化物与烯烃的1,3-偶极环加成反应，以中等至良好的产率获得了多种噻唑取代的α-羟基羰基化合物。开环反应。此外，可以通过一锅，两步脱水过程从合成的α-羟基羰基化合物以优异的产率生产相应的2-烯基噻唑。
• Derivatives of substituted N-alkyl imidazoles
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04078071A1

  公开（公告）日：1978-03-07

  Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl or one of the above substituted in the phenyl ring with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from 1 to 8 with the proviso that n is not 1 when R.sup.1 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.

  该式的化合物 ##STR1## 中，其中 R.sup.1 和 R.sup.2 分别独立地为苯基、苯基直链低碳烷基或苯基直链低碳烯基，或上述之一在苯环中被一个或多个取代基取代，所述取代基独立地选自由一至四个碳原子的低碳烷基、卤素和三氟甲基；X 为氧或硫；n 为1至8的整数，但当 R.sup.1 为苯基或取代苯基时，n 不为1；其抗菌酸盐酸盐可用作抗真菌、抗细菌和抗原虫剂。
• Highly Enantioselective Intermolecular Cross Rauhut-Currier Reaction Catalyzed by a Multifunctional Lewis Base Catalyst
  作者：Xuelin Dong、Ling Liang、Erqing Li、You Huang

  DOI：10.1002/anie.201409744

  日期：2015.1.26

  The highly enantioselective intermolecular cross Rauhut–Currier reaction of different active olefins catalyzed by a multifunctional chiral Lewis base was reported. The RC products were obtained in excellent yields (up to 98 %), high chemo‐ and enantioselectivity (up to 96 % ee). The reaction could be performed on a gram scale using 1 mol % of the multifunctional phosphine catalyst.

  据报道，多功能手性路易斯碱可催化不同活性烯烃的高度对映选择性分子间交叉Rauhut-Currier反应。获得的RC产品收率极高（高达98％），化学和对映体选择性高（ee高达96％  ）。该反应可以使用1mol％的多官能膦催化剂以克为单位进行。
• Direct Catalytic Enantioselective Vinylogous Aldol Reaction of Allyl Ketones to Pyrazole-4,5-diones
  作者：Bidisha Ray、Santanu Mukherjee

  DOI：10.1021/acs.joc.8b01566

  日期：2018.9.21

  The first catalytic enantioselective vinylogous nucleophilic addition to pyrazole-4,5-diones is reported. Using quinine-derived bifunctional tertiary amino-amide as the catalyst, this direct aldol reaction of allyl ketones is shown to proceed exclusively in γ- and E-selective manner to generate pyrazolone derivatives, bearing an oxygen-containing quaternary stereogenic center, in good yields with moderate

  据报道，向吡唑-4，5-二酮的第一催化对映选择性乙烯基亲核加成反应。使用奎宁衍生的双官能叔氨基酰胺作为催化剂，表明烯丙基酮的直接醛醇缩合反应仅以γ和E选择性方式进行，生成吡唑烷酮衍生物，并带有含氧的季立体中心，收率高。具有中等至高对映选择性（高达97：3 er）。