(E)-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one | 4875-89-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (E)-2-(pyridin-4-ylmethylene)-2,3-dihydroinden-1-one；(2E)-2-(pyridin-4-ylmethylidene)-3H-inden-1-one
• CAS: 4875-89-2
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: UFLITIQLRTXBDW-UKTHLTGXSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  417.8±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (E)-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one 以 乙醇 为溶剂， 反应 48.0h， 以22%的产率得到2-(Pyridin-4-yl)-methylene-indan-1-one
  参考文献：
  名称：

  Aromatase Inhibitors. Syntheses and Structure-Activity Studies of Novel Pyridyl-Substituted Indanones, Indans, and Tetralins

  摘要：

  The (E)-2-(4-pyridylmethylene)-1-indanones (E)-1-(E)-5[(E)-1, H; (E);2, 4-OCH3; (E)-3, 5-OCH3; (E)-4, 4-OH; (E)-5,5-OH] were obtained by aldol condensation of the corresponding 1-indanones with 4-pyridinecarboxaldehyde, and in case of the OH compound (E)-4 subsequent ether cleavage of (E)-2. The synthesis of the (Z)-isomers (Z)-1-(Z)-3 [(Z)-1, H; (Z)-2, 4-OCH3; (Z)-3, 5-OCH3] was accomplished by UV irradiation of the corresponding (E)-isomers. Catalytic hydrogenation of (E)-1-(E)-3 gave the 2-(4-pyridylmethyl)-1-indanones 6-8 (6, H; 7, 4-OCH3; 8, 5-OCH3). The 2-(4-pyridylmethyl)-substituted indans 11-13 (11, H; 12, 4-OCH3; 13, 5-OCH3) and the tetralins 16-19 (16, H; 17, 5-OCH3; 18, 6-OCH3; 19, 7-OCH3) were obtained by reduction of the corresponding ketones using N2H4/KOH. The 2-(4-pyridylmethyl)-substituted indanones 9 (4-OH) and 10 (5-OH), indans 14 (4-OH) and 15 (5-OH), and tetralins 20-22 (20, 5-OH; 21, 6-OH; 22, 7-OH) were synthesized by ether cleavage of the corresponding OCH3 compounds. All compounds showed inhibition of human placental aromatase exhibiting relative potencies from 0.9 [(E)-4] to 163 [18; aminoglutethimide (AC) potency E 1]. Compounds 13 and 18 showed competitive type of inhibition and a type II difference spectrum, indicating the interaction of the pyridyl-N with the central Fe(III) ion of the cytochrome P450 heme component. Only the OH-substituted indans and tetralins inhibited bovine adrenal desmolase with maximum activity shown by 20 and 22 (12% inhibition, 25 mu M; AG, 53 % inhibition, 25 mu M). In vivo, however, all tested aromatase inhibitors (6, 8, 10, 14, 15, 18 and 20) were less active than AG concerning the inhibition of the uterotrophic activity of androstenedione (6, 8, 10, 15), the reduction of the plasma estradiol concentration (14, 20), and the mammary carcinoma (MC) inhibiting properties (18, 20; androstenedione-stimulated juvenile rats, pregnant mares' serum gonadotropin-primed rats as well as dimethylbenzanthracene-induced MC of the Sprague-Dawley rat, postmenopausal experiment). Since no affinity to the estrogen receptor was demonstrated (20), estrogenic effects as a cause for the poor tumor inhibiting activity have to be excluded.

  DOI：

  10.1021/jm00035a007
• 作为产物：
  描述：

  4-吡啶甲醛 、 1-茚酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以95%的产率得到(E)-2-(pyridin-4-ylmethylene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  卤代芳基和杂环标记的2,3-二氢-1 H-茚满-1候选物的超快合成，抗菌和抗真菌研究

  摘要：

  我们描述了卤代芳基和杂环标记的2，3-二氢-1 H-茚满一酮衍生物的成功合成，以及它们的抗菌和抗真菌特性。通过研磨，搅拌和超声辐照方法合成了来自2，3-二氢-1 H-茚基-1-一的总共15种衍生物。这些发现表明，超声技术在时间和合成性能方面越来越令人满意。测试了合成的化合物对两种革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）和两种革兰氏阴性菌（大肠杆菌和寻常变形杆菌）以及两种真菌剂的抗菌活性。黑曲霉和白色念珠菌）。发现大多数化合物都具有强大的抗菌作用，并具有广谱抗菌活性。同样，几乎没有化合物显示出对黑曲霉和白色念珠菌具有有效的抗真菌特性。通过FT-IR，1 H NMR，13 C NMR和HRMS光谱技术对合成的化合物进行表征。 图形摘要

  DOI：

  10.1007/s00706-021-02772-0

文献信息

• Novel Series of Imidazolyl Substituted Steroidal and Indan-1-One Derivatives
  申请人：Bansal Ranju

  公开号：US20090137541A1

  公开（公告）日：2009-05-28

  The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)

  本发明提供了一种新的咪唑基取代类固醇和茚环-1-酮衍生物及其盐，其具有以下一般结构式（A和B）。
• Synthesis of benzylidenecycloalkan-1-ones and 1,5-diketones under Claisen–Schmidt reaction: Influence of the temperature and electronic nature of arylaldehydes
  作者：Beatriz Lantaño、José M. Aguirre、Eleonora V. Drago、Mariela Bollini、Diego J. de la Faba、Jorge D. Mufato

  DOI：10.1080/00397911.2017.1367819

  日期：2017.12.2

  involves Michael addition reaction, which is also dependent on the temperature. Theoretical studies using density-functional theory allowed understanding the chemical reactivity and the site selectivity of α,β-enones used in this work through the calculation of global and local electrophilicity on C–β. Both the electrophilicity of C-β and the temperature led the course of reaction toward the formation of

  摘要 在此，我们展示了在经典 Claisen-Schmidt 缩合条件下苯并环烷-1-酮和芳醛反应中反应温度和芳醛电子性质的影响结果。通过多组分反应获得的苯并环烷烃-1-酮和/或螺多环-1,5-二酮的2-亚芳基衍生物取决于芳醛的电子性质和反应温度。此外，在相同条件下，2-亚芳基茚满-1-酮通过涉及迈克尔加成反应的过程提供双-茚满-1,5-二酮，该过程也取决于温度。使用密度泛函理论的理论研究可以理解 α 的化学反应性和位点选择性，通过计算 C-β 上的全局和局部亲电性，本工作中使用的 β-烯酮。C-β 的亲电性和温度导致反应过程朝着形成羟醛缩合、羟醛缩合/迈克尔加成和羟醛缩合/二聚产物的方向发展。这项工作是第一个对双茚满 1,5-二酮进行结构和构型分配的工作。图形概要
• [EN] PROCESS FOR THE PREPARATION OF DONEPEZIL AND DERIVATIVES THEREOF<br/>[FR] PROCEDE DE PREPARATION DE DONEPEZIL ET DE SES DERIVES
  申请人：RANBAXY LAB LTD

  公开号：WO2004082685A1

  公开（公告）日：2004-09-30

  The invention relates to processes for the preparation of piperidylmethyl-indanones, and to the use of these compounds as intermediates for the preparation of benzyl-piperidylmethyl-indanones which are active compounds for the treatment of CNS disorders. The invention also relates to a process for the preparation of donepezil or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions that include the donepezil or a pharmaceutically acceptable salt thereof.

  本发明涉及制备哌啶甲基-茚烷酮的方法，以及使用这些化合物作为中间体制备苯甲基-哌啶甲基-茚烷酮，后者是治疗中枢神经系统疾病的活性化合物。本发明还涉及制备多奈哌齐或其药学上可接受的盐的方法，以及包括多奈哌齐或其药学上可接受的盐的制药组合物。
• Novel process for preparing dopenzil and its derivatives
  申请人：Zhang Hesheng

  公开号：US20070072905A1

  公开（公告）日：2007-03-29

  A process for producing a Donepezil derivative represented by the formula (I), wherein R 1 , R 2 , R 3 , and R 4 each independently represents H, F, an alkyl having from 1 to 4 carbon atoms, or an alkoxy having from 1 to 4 carbon atoms; R 5 represents a phenyl or a substituted phenyl; and n is an integer from 0 to 2, characterized in that the process comprises: (a) a reaction of 4-pyridinecarboxaldehyde with a compound of formula (II) in the presence of a strong acid HX to form a compound of formula (III); (b) a catalytic hydrogenation of a compound of formula (III) or a compound of formula (V) to yield a compound of formula (IV); and (c) an alkylation reaction of a compound of formula (IV) to yield a compound of formula (I).

  一种生产Donepezil衍生物的方法，该衍生物由式（I）表示，其中R1，R2，R3和R4分别独立地表示H，F，具有1至4个碳原子的烷基或具有1至4个碳原子的烷氧基; R5表示苯或取代苯; n是0至2的整数，其特征在于该方法包括：（a）4-吡啶甲醛与式（II）化合物在强酸HX存在下反应，形成式（III）化合物; （b）式（III）化合物或式（V）化合物的催化氢化，得到式（IV）化合物; （c）式（IV）化合物的烷基化反应，得到式（I）化合物。
• Stable lamotrigine pharmaceutical compositions and processes for their preparation
  申请人：Kumar Yatendra

  公开号：US20070129549A1

  公开（公告）日：2007-06-07

  The invention relates to processes for the preparation of piperidylmethyl-indanones, and to the use of these compounds as intermediates for the preparation of benzyl-piperidylmethyl-indanones which are active compounds for the treatment of CNS disorders. The invention also relates to a process for the preparation of donepezil or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions that include the donepezil or a pharmaceutically acceptable salt thereof.

  本发明涉及制备哌啶基甲基-茚酮类化合物的方法，以及将这些化合物用作制备苯基-哌啶基甲基-茚酮类活性化合物（用于治疗中枢神经系统疾病）的中间体的用途。本发明还涉及制备多奈哌齐或其药学上可接受的盐的方法，以及包括多奈哌齐或其药学上可接受的盐的制药组合物。