4-(3,5-二甲基苯基)丁-3-烯-2-酮 | 1356967-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 4-(3,5-二甲基苯基)丁-3-烯-2-酮
• 英文名称: 4-(3,5-dimethylphenyl)but-3-en-2-one
• CAS: 1356967-21-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: PCFYIQMDJNXXDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  294.9±9.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-(3,5-二甲基苯基)丁-3-烯-2-酮 在 甲醇 、 sodium tetrahydroborate 作用下， 生成
  参考文献：
  名称：

  通过串联硼烷和钯催化吡啶的对映选择性 C3-烯丙基化

  摘要：

  开发了一种用于吡啶的高度对映选择性 C3 烯丙基化反应的一锅三步方法。该方法包括硼烷催化的脱芳基吡啶硼氢化反应、钯催化的脱芳基中间体的对映选择性烯丙基化反应，以及最后的空气氧化反应。该方法适用于多种吡啶、N-杂芳烃和烯丙酯。

  DOI：

  10.1002/anie.202307697
• 作为产物：
  描述：

  3,5-二甲基苯甲醛 、 1-三苯基膦-2-丙酮 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 4-(3,5-二甲基苯基)丁-3-烯-2-酮
  参考文献：
  名称：

  Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

  摘要：

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.039

文献信息

• Enantioselective Aminocatalytic [2 + 2] Cycloaddition through Visible Light Excitation
  作者：Thomas Rigotti、Rubén Mas-Ballesté、José Alemán

  DOI：10.1021/acscatal.0c01413

  日期：2020.5.1

  to obtain enantioenriched cyclobutanes through [2 + 2] photocycloaddition under visible light irradiation is presented. This metal-free process does not require the use of any external photocatalyst, as it is catalyzed by a simple diamine which, upon condensation with an enone substrate, forms an iminium ion intermediate that absorbs in the visible light region. The direct excitation of such an intermediate

  提出了在可见光下通过[2 + 2]光环加成反应获得对映体富集的环丁烷的不对称氨基催化活化策略。这种无金属的方法不需要使用任何外部光催化剂，因为它是由简单的二胺催化的，该二胺与烯酮底物缩合后，形成在可见光区域吸收的亚胺离子中间体。这种中间体的直接激发导致电荷转移（CT）激发态，该态以良好的对映异构体和非对映异构体比率和高收率解锁立体控制的分子间光环加成反应。最后，进行了DFT计算和实验以支持电荷转移行为和机理建议。
• Electroreductive 4-Pyridylation of Electron-deficient Alkenes with Assistance of Ni(acac)₂
  作者：Sheng Zhang、Lijun Li、Xinru Li、Junqi Zhang、Kun Xu、Guigen Li、Michael Findlater

  DOI：10.1021/acs.orglett.0c01014

  日期：2020.5.1

  An electroreductive 4-pyridylation of activated alkenes was developed in an undivided cell with the assistance of Ni(acac)(2) (acac = acetylacetone). This novel protocol is compatible with a broad range of electron-poor alkenes, which are commonly regarded as challenging substrates in the previous conventional approaches. Moreover, a series of cyclic voltammetric experiments were conducted to reveal the unique role of Ni(acac)(2) differentiating reduction process of reaction partners.
• Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells
  作者：Wei Zhang、Radhia Benmohamed、Anthony C. Arvanites、Richard I. Morimoto、Robert J. Ferrante、Donald R. Kirsch、Richard B. Silverman

  DOI：10.1016/j.bmc.2011.11.039

  日期：2012.1

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.
• Enantioselective C3‐Allylation of Pyridines via Tandem Borane and Palladium Catalysis
  作者：Jun‐Jie Tian、Rui‐Rui Li、Gui‐Xiu Tian、Xiao‐Chen Wang

  DOI：10.1002/anie.202307697

  日期：2023.8.21

  A one-pot, three-step method for highly enantioselective C3-allylation reactions of pyridines was developed. The method involved borane-catalyzed dearomative pyridine hydroboration, palladium-catalyzed enantioselective allylation of the dearomatized intermediate, and finally oxidation by air. The method was applicable to a broad range of pyridines, N-heteroarenes, and allylic esters.

  开发了一种用于吡啶的高度对映选择性 C3 烯丙基化反应的一锅三步方法。该方法包括硼烷催化的脱芳基吡啶硼氢化反应、钯催化的脱芳基中间体的对映选择性烯丙基化反应，以及最后的空气氧化反应。该方法适用于多种吡啶、N-杂芳烃和烯丙酯。