5-(4-tert-butylphenyl)cyclohexane-1,3-dione | 946686-29-9

• 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: 5-(4-tert-butylphenyl)cyclohexane-1,3-dione
• 英文别名: 5-(4-t-butylphenyl)-1,3-cyclohexanedione
• CAS: 946686-29-9
• 化学式: C₁₆H₂₀O₂
• mdl: MFCD13873932
• 分子量: 244.334
• InChiKey: DOBCYMOHKDQMLM-UHFFFAOYSA-N

物化性质

• 沸点：
  394.6±42.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  三羟甲基丙烷 、 5-(4-tert-butylphenyl)cyclohexane-1,3-dione 在 phosphotungstic acid 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以14.8 g的产率得到5-(4-t-butylphenyl)-1,3-cyclohexanedione trimethylolpropane diacetal
  参考文献：
  名称：

  [EN] CYCLIC DIOL COMPOUND, PRODUCTION METHOD FOR SAID COMPOUND, AND USE OF SAID COMPOUND
  [FR] COMPOSÉ DIOL CYCLIQUE, PROCÉDÉ DE PRODUCTION ET UTILISATION DUDIT COMPOSÉ
  [JA] 環式ジオール化合物、該化合物の製造方法及び該化合物の用途

  摘要：

  本发明提供了一种环式二元醇化合物或其制备方法，其作为树脂原料和树脂改性剂对聚酯树脂，聚碳酸酯树脂，环氧树脂，聚氨酯树脂，聚丙烯酸酯树脂，聚甲基丙烯酸酯树脂，聚酯多元醇树脂等都很有用。本发明涉及化合物表示为通式（1）[其中，R1分别表示相同或不同的氢原子，具有6-12个碳原子的芳基或具有1-4个直链或支链烷基；X表示由通式（a），通式（b），通式（c）或通式（d）表示的基团。 （在式（a）-（d）中，波浪线表示连接部分。R2分别表示相同或不同的氢原子，氟原子，氯原子，溴原子，具有1-4个直链或支链烷基或具有1-7个直链或支链的烷氧基。]，以及其制备方法和用途。

  公开号：

  WO2022091990A1
• 作为产物：
  描述：

  对叔丁基苯甲醛 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 36.0h， 生成 5-(4-tert-butylphenyl)cyclohexane-1,3-dione
  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

• Cinchona Squaramide‐Catalyzed Intermolecular Desymmetrization of 1,3‐Diketones Leading to Chiral 1,4‐Dihydropyridines
  作者：Maciej Dajek、Agnieszka Pruszczyńska、Krzysztof A. Konieczny、Rafał Kowalczyk

  DOI：10.1002/adsc.202000455

  日期：2020.9.8

  Addition of prochiral cyclic 1,3‐diketones to Michael acceptors applying bifunctional Cinchona‐derived squaramides resulted in chiral adducts with stereoselectivities of up to 99% ee and allowed for desymmetrization of the nucleophile. These labile hemiacetal intermediates were transformed to new 1,4‐dihydropyridines with high diastereoselectivities and no erosion of optical purity. Their further oxidation

  在使用双官能金鸡纳衍生的方酰胺的迈克尔受体上添加前手性环状1,3-二酮会导致手性加合物的立体选择性高达99％ee，并允许亲核试剂脱对称。这些不稳定的半缩醛中间体被转化为新的1,4-二氢吡啶，具有高非对映选择性，且不会破坏光学纯度。它们进一步氧化为吡啶，然后进行费舍尔吲哚化，提供了手性吡啶吲哚。
• Cyclohexane-1,3-Diones for Use in the Treatment of Amyotrophic Lateral Sclerosis
  申请人：Kirsch Donald R.

  公开号：US20120264765A1

  公开（公告）日：2012-10-18

  The present invention relates to the identification of provided cyclohexane-1,3-diones (CHD compounds) and pharmaceutical compositions thereof for treating subjects with amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. The invention also provides methods of preparing the provided CHD compounds.

  本发明涉及提供的环己烷-1,3-二酮（CHD化合物）的鉴定及其制备的药物组合物，用于治疗患有肌萎缩侧索硬化症（ALS）和其他神经退行性疾病的受试者。本发明还提供了制备所述CHD化合物的方法。
• Copper-catalyzed one-pot [3 + 2] cycloadditions of ethynyl indoloxazolidones with 1,3-cyclohexanediones
  作者：Qing-Qiang Su、Ruo-Nan Wang、Yong-Zheng Lv、Ya-Xin Fan、Shan Li、Hong-Li Huang、Ji-Yuan Du

  DOI：10.1039/d3ob00332a

  日期：——

  units in natural products and medicinal molecules, and methods for their introduction are of fundamental importance. Here we report one-pot cycloadditions of ethynyl indoloxazolidones with 1,3-cyclohexanediones enabled by copper catalysis, leading to a series of functionalized furan derivatives in good yields. This method features mild reaction conditions, high efficiency, and wide substrate scope

  稠合呋喃是天然产物和药用分子中常见的单元，引入它们的方法至关重要。在这里，我们报告了通过铜催化实现的乙炔基吲哚恶唑烷酮与 1,3-环己二酮的一锅法环加成，从而以良好的收率生成了一系列功能化的呋喃衍生物。该方法反应条件温和、效率高、底物适用范围广。
• US8722939B2
  申请人：——

  公开号：US8722939B2

  公开（公告）日：2014-05-13
• US9162968B2
  申请人：——

  公开号：US9162968B2

  公开（公告）日：2015-10-20