3,3,6,6,9-pentamethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione | 3357-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,3,6,6,9-pentamethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
• 英文别名: 3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione；3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione；3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione；3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione；3,3,6,6,9-pentamethyl-2,4,5,7,9,10-hexahydroacridine-1,8-dione
• CAS: 3357-11-7
• 化学式: C₁₈H₂₅NO₂
• mdl: MFCD00469074
• 分子量: 287.402
• InChiKey: BZTGVBSTOUKXCI-UHFFFAOYSA-N

物化性质

• 熔点：
  258-260 °C
• 沸点：
  427.2±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3,6,6,9-pentamethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以90%的产率得到3,3,6,6,9-pentamethyl-1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione
  参考文献：
  名称：

  Shanmugasundaram; Ramakrishnan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 1, p. 17 - 20

  摘要：

  DOI：
• 作为产物：
  描述：

  5,5,5',5'-tetramethyl-2,2'-ethylidene-bis-cyclohexane-1,3-dione 在 乙酸铵 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以92%的产率得到3,3,6,6,9-pentamethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
  参考文献：
  名称：

  Synthesis, Characterization, and Electrochemistry of Some Acridine-1,8-dione Dyes

  摘要：

  The synthesis, characterization, and electrochemical behavior of some acridinedione derivatives are reported. Cyclic voltammetric studies show that all the dyes undergo irreversible oxidation irrespective of the substitution on the nitrogen. The product formed on oxidation is the aromatic derivative in the case of N-H compounds and the acridinium salt in the case of the N-substituted compounds, which have been isolated and characterized. Formation of an intermediate carbon-centered radical is observed as evidenced by ESR spin-trapping experiments. A mechanistic scheme for the electrochemical oxidation is proposed. On carrying out reduction after oxidation, different products are formed depending on the substitution on the nitrogen. There is no reduction of the oxidized product in the case of N-H compounds, and compounds with substitution on nitrogen undergo reduction consistent with the observation in N-alkylpyridinium salts.

  DOI：

  10.1021/jo9600316

文献信息

• Vinyl esters as effective acetaldehyde surrogates in [4 + 1] cycloaddition based multicomponent cascade
  作者：Manoj Kumar、Sourav Bagchi、Anuj Sharma

  DOI：10.1039/c5ra10073a

  日期：——

  A new multicomponent cascade has been designed by utilizing vinyl esters as effective acetaldehyde surrogate. While most of the cyclic α-ketoenols underwent a facile three component conversion to annulated furans, phenols such as naphthol and sesamol got simply acylated under the same reaction conditions. This microwave assisted method provides clean access to a wide range of functionalised furans

  通过利用乙烯基酯作为有效的乙醛替代物，设计了一种新的多组分级联反应。尽管大多数环状α-酮烯醇都容易地由三组分转化为环状呋喃，但在相同的反应条件下，酚（如萘酚和芝麻酚）却被简单地酰化了。这种微波辅助方法可在短时间内清洁范围广泛的功能化呋喃。
• Environmentally Friendly and Efficient Synthesis of Various 1,4-Dihydropyridines in Pure Water
  作者：Guan-Wu Wang、Jing-Jing Xia、Chun-Bao Miao、Xue-Liang Wu

  DOI：10.1246/bcsj.79.454

  日期：2006.3

  An environmentally friendly and efficient synthesis of a series of 1,4-dihydropyridines was developed by the practical one-pot reactions of aldehydes with ammonium acetate and 1,3-dicarbonyl compounds such as alkyl acetoacetate, 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, and 2,4-pentanedione in water without any additives under refluxing conditions.

  通过醛类与乙酸铵以及1,3-二羰基化合物（如乙基乙酰乙酸酯、5,5-二甲基-1,3-环己二酮、1,3-环己二酮和2,4-戊二酮）在水中的实际一步反应，无需任何添加剂并在回流条件下，开发了一系列1,4-二氢吡啶的环境友好且高效的合成方法。
• A facile biodegradable chitosan‐SO3H catalyzed acridine‐1,8‐dione synthesis with molecular docking, molecular dynamics simulation and density functional theory against human topoisomerase II beta and Staphylococcus aureus tyrosyl‐tRNA synthetase
  作者：Nusrat Sahiba、Ayushi Sethiya、Jay Soni、Pankaj Teli、Ankita Garg、Shikha Agarwal

  DOI：10.1016/j.molstruc.2022.133676

  日期：2022.11

  molecular dynamics simulations, protein-ligand interaction energy calculations and DFT studies. Among all, compounds 4e, 4f (– 11.8 kcal/mol), 4g, 4x and 4c (– 10.8 kcal/mol), 4d, 4i, 4s were the most potent against Human Topoisomerase II beta (3QX3) and Staphylococcus aureus (S. aureus) tyrosyl-tRNA synthetase (1JIJ), respectively and displayed good binding affinity and interaction pattern. Easy availability

  已经使用可生物降解的非均相催化剂壳聚糖-SO 3 H 在环境反应条件下研究了一种高效且环保的假一锅法合成吖啶-1,8-二酮。使用壳聚糖-SO 3 H 催化剂在室温下，二甲酮、醛和乙酸铵在乙醇水溶液中的高效反应显示出高产率，反应时间短。通过分子对接和分子动力学模拟、蛋白质-配体相互作用能计算和DFT研究，进一步研究了分子的生物活性。其中，化合物4e、4f (– 11.8 kcal/mol) 、4g、4x和4c (– 10.8 kcal/mol) 、4d、4i、4s分别对人拓扑异构酶 II β ( 3QX3) 和金黄色葡萄球菌( S. aureus)酪氨酰-tRNA 合成酶( 1JIJ) 最有效，并显示出良好的结合亲和力和相互作用模式。易于获得底物和催化剂，使用可生物降解和可回收的聚合固体酸催化剂，避免使用有毒和金属试剂，操作简单，无需柱层析，易于后处理，清洁反应曲线，高收率 (70–95%)
• Fe₃O₄@SiO₂ core/shell functionalized by gallic acid: a novel, robust, and water-compatible heterogeneous magnetic nanocatalyst for environmentally friendly synthesis of acridine-1,8-diones
  作者：Zahra Firoozi、Dariush Khalili、Ali Reza Sardarian

  DOI：10.1039/d4ra00629a

  日期：2024.4.3

  exploited in the multicomponent synthesis of acridine-1,8-dione derivatives by considering the green chemistry matrix and under mild conditions. Various aldehydes and amines were smoothly reacted with dimedone, affording the desired products in good to excellent yields. The introduction of sulfonic groups using gallic acid allowed the development of a water-compatible and highly recyclable catalytic

  在这项研究中，我们使用没食子酸稳定的 Fe 3 O 4 @SiO 2核/壳方便地制备了一种新型的坚固的非均相磁性纳米催化剂。通过各种物理化学技术对催化剂进行了全面表征，包括红外光谱（FT-IR）、X射线衍射（XRD）、动态光散射（DLS）、透射电子显微镜（TEM）、场发射扫描电子显微镜（FE-SEM） )、热重分析 (TGA)、电位滴定、能量色散 X 射线微量分析 (EDX)、振动样品磁力计 (VSM)、zeta 电位分析和 BET。然后，通过考虑绿色化学基质和在温和的条件下，新开发的磺化纳米催化剂的潜在能力被用于吖啶-1,8-二酮衍生物的多组分合成。各种醛和胺与双甲酮顺利反应，以良好至优异的产率提供所需的产物。使用没食子酸引入磺酸基团可以开发出水相容且高度可回收的催化系统，用于水环境中的反应。制备的催化剂可以很容易地磁分离并重复使用八次而不会显着损失活性。该催化体系的显着特点是合成效率高
• Carbon transfer reactions of functionalized oxazolidines and their open chain enamine tautomers to enamine nucleophiles. A facile synthesis of substituted pyridines and ring annulated derivatives
  作者：Kamaljit Singh、Jasbir Singh、Harjit Singh

  DOI：10.1016/s0040-4020(97)10349-0

  日期：1998.1

  Oxazolidines substituted at C-2 with -CH2-EW(-CO-, etc.) and capable of existing as ring-chain (enamine) tautomers' react with cyclic, acyclic and heterocyclic enamine derivatives in a 1:1 stoichiometric manner to provide a versatile synthesis of substituted pyridines and their ring annulated derivatives. (C) 1997 Elsevier Science Ltd. All rights reserved.