3,3-dimethyl-3,4-dihydroacridin-1(2H)-one | 72989-31-2

• 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-dimethyl-3,4-dihydroacridin-1(2H)-one
• 英文别名: 3,4-dihydro-3,3-dimethyl-1(2H)-acridinone；3,4-dihydro-3,3-dimethylacridin-1(2H)-one；3,3-dimethyl-3,4-dihydro-2H-acridin-1-one；3,3-Dimethyl-3,4-dihydro-2H-acridin-1-on；3,4-Dihydro-3,3-dimethyl-1(2H)-acridon；3,3-dimethyl-2,4-dihydroacridin-1-one
• CAS: 72989-31-2
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: NGIJYZXCLGHEKG-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  376.6±11.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-3,4-dihydroacridin-1(2H)-one 在 甲酸 、 sodium formate 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 以96%的产率得到3,3-Dimethyl-3,4,9,10-tetrahydro-2H-acridin-1-one
  参考文献：
  名称：

  使用固定在联吡啶周期中介孔有机硅上的可回收铑催化剂转移氮杂环的氢化作用†

  摘要：

  描述了使用固定在联吡啶-周期介孔有机二氧化硅（BPy-PMO）上的铑催化剂进行不饱和氮杂环的转移氢化。固定化的催化剂通过混合制备的[Cp *的RhCl 2 ] 2（CP * =η 5 -C 5我5）在60°C的DMF中使用BPy-PMO粉末，并通过氮气吸附测量，固态NMR光谱，X射线衍射，能量色散X射线光谱和透射电子显微镜进行表征。在催化剂的存在下，将各种不饱和氮杂环进行转移氢化，以高收率得到相应的产物。固定的催化剂可以很容易地通过离心回收，并在转移氢化过程中重复使用几次。

  DOI：

  10.1039/c7cy02167d
• 作为产物：
  描述：

  3,3-Dimethyl-3,4,9,10-tetrahydro-2H-acridin-1-one 在 对苯醌 作用下， 以100%的产率得到3,3-dimethyl-3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  One-Pot DBU-Promoted Synthesis of Hydroacridinones and Spirohexahydropyrimidines

  摘要：

  The potential hydroacridinone synthesis using simple and inexpensive starting materials, namely 1,3-dicarbonyl compounds, anilines, formaldehyde and DBU as a stoichiometric base was explored. As a result, from the reaction of 1,3-cyclohexanedione and dimedone tetrahydroacridinones were the main reaction products along with small yields of their oxidation products, the dihydroacridinones, whereas in the case of 2-acetylcyclohexanone spirohexahydropyrimidines were isolated in very good yields. Plausible mechanistic schemes for the formation of all products are proposed.

  DOI：

  10.1055/s-0033-1339922

文献信息

• An unexpected one-pot synthesis of multi-substituted quinolines via a cascade reaction of Michael/Staudinger/aza-Wittig/aromatization of ortho-azido-β-nitro-styrenes with various carbonyl compounds
  作者：Zhi-Hua Yu、Hu-Fei Zheng、Wei Yuan、Zi-Long Tang、Ai-Dong Zhang、De-Qing Shi

  DOI：10.1016/j.tet.2013.07.050

  日期：2013.9

  Multi-substituted quinolines 3 were unexpectedly prepared from a cascade reaction of ortho-azido-β-nitro-styrenes with various carbonyl compounds. This method takes advantages of mild condition, simple work-up, high yield as well as wide substrate scope, which makes this method powerful for one-pot synthesis of multi-substituted quinolines.

  由邻-叠氮基-β-硝基-苯乙烯与各种羰基化合物的级联反应出乎意料地制备了多取代的喹啉3。该方法具有条件温和，后处理简单，收率高，底物范围广等优点，可用于一锅法合成多取代喹啉。
• Iron/acetic acid mediated intermolecular tandem C–C and C–N bond formation: an easy access to acridinone and quinoline derivatives
  作者：R. R. Rajawinslin、Sachin D. Gawande、Veerababurao Kavala、Yi-Hsiang Huang、Chun-Wei Kuo、Ting-Shen Kuo、Mei-Ling Chen、Chiu-Hui He、Ching-Fa Yao

  DOI：10.1039/c4ra06410k

  日期：——

  An efficient iron/acetic acid mediated one pot reductive cyclization protocol was successfully developed for the synthesis of acridinone and quinoline derivatives.

  一种高效的铁/醋酸介导的一锅式还原环化方案成功开发，用于合成吖啶酮和喹啉衍生物。
• Palladium-Catalyzed Coupling of Vinylogous Amides with Aryl Halides:  Applications to the Synthesis of Heterocycles
  作者：Scott D. Edmondson、Anthony Mastracchio、Emma R. Parmee

  DOI：10.1021/ol000031z

  日期：2000.4.1

  of vinylogous amides with aryl bromides and chlorides. The scope of this reaction with respect to the aryl component is investigated. Additionally, a tandem reaction sequence in which the above coupling is followed by an intramolecular Heck reaction is presented. These reactions can be applied to high-yielding, one-pot syntheses of nitrogen-containing heterocycles.

  [式中：见正文]本文描述的是乙烯基催化剂与芳基溴化物和氯化物的钯催化偶联的第一个例子。研究了该反应相对于芳基组分的范围。另外，提出了串联反应序列，其中上述偶联之后是分子内Heck反应。这些反应可用于高产的一锅合成含氮杂环。
• Ruthenium-catalysed C-alkylation of 1,3-dicarbonyl compounds with primary alcohols and synthesis of 3-keto-quinolines
  作者：Elena Cini、Elena Petricci、Giuseppina I. Truglio、Marialaura Vecchio、Maurizio Taddei

  DOI：10.1039/c6ra03585j

  日期：——

  mono-alkylation of 1,3-diketones using alcohols is possible in the presence of catalytic amounts of Ru(CO)(PPh3)3HCl and 10% mol of the Hantzsch ester. The borrowing hydrogen process between the catalyst and the dihydropyridine/pyridine couple prevents the common double alkylation of the Knoevenagel adduct without the need of stoichiometric reducing agents or sacrificial nucleophiles. The reaction was applied to

  在催化量的Ru（CO）（PPh 3）3 HCl和10％摩尔的Hantzsch酯存在下，使用醇对1,3-二酮进行单烷基化是可能的。催化剂和二氢吡啶/吡啶对之间的借入氢过程可防止Knoevenagel加合物的常见双烷基化，而无需化学计量的还原剂或牺牲亲核试剂。该反应用于内酯中间体的合成，以制备抗肥胖药奥利司他。此外，在相同的Ru催化下，与邻氨基苄醇发生Friedländer反应，从而获得不同的3-酮取代的喹啉。
• Fe ₂ O ₃ @[proline]–CuMgAl–LDH: A magnetic bifunctional copper and organocatalyst system for one‐pot synthesis of quinolines and 2 <i>H</i> ‐indazoles in green media
  作者：Naghmeh Esfandiary、Akbar Heydari

  DOI：10.1002/aoc.5760

  日期：2020.9

  A novel magnetic core–shell Fe2O3@[proline]–CuMgAl–L(ayered)D(ouble)H(ydroxide) was designed as an efficient bifunctional catalytic system. To this end, Cu (II) was combined with Mg and Al in the LDH structure and l‐proline was intercalated between LDH layers in order to perform a straightforward synthesis of quinolines and 2H‐indazoles as two important pharmaceutical N‐aryl‐substituted heterocyclic

  设计了一种新型的磁性核-壳Fe 2 O 3 @ [脯氨酸] -CuMgAl-L（氧化）D（双）H（氢氧化物）作为有效的双功能催化体系。为此，在LDH结构中将Cu（II）与Mg和Al结合，并在LDH层之间插入l-脯氨酸，以进行喹啉和2H-吲唑的直接合成，这是两种重要的药物N芳基取代的杂环化合物。在这方面，通过在温和的条件下在叠氮化胆碱介质中连续缩合而采用的简便方法，其起试剂和溶剂的作用，避免有毒溶剂和有害的叠氮化试剂。这些技术在使用绿色介质，减少起始原料，达到更高的收率以及缩短反应时间和降低温度方面提供了可观的改进。总之，发现该催化剂可以重复使用五次而活性没有明显损失。