ethyl 2-(2-piperidinylidene)acetate | 25654-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl 2-(2-piperidinylidene)acetate
• 英文别名: piperidin-2-ylidene-acetic acid ethyl ester；Ethyl (piperidin-2-ylidene)acetate；ethyl 2-piperidin-2-ylideneacetate
• CAS: 25654-24-4；108139-97-5；50796-18-4
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: VTIIQRXRYKVQEA-UHFFFAOYSA-N

物化性质

• 沸点：
  271.7±29.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-piperidinylidene)acetate 在 硼酸 作用下， 反应 0.75h， 以70%的产率得到6-methyl-2,3,4,5-tetrahydro-pyridine
  参考文献：
  名称：

  Cyclic β-enaminoesters decarboxylation with boric acid: A convenient synthesis of cyclic imines

  摘要：

  DOI：

  10.1016/s0040-4039(00)96122-7
• 作为产物：
  描述：

  ethyl 7-azido-3-oxoheptanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 反应 1.0h， 生成 ethyl 2-(2-piperidinylidene)acetate
  参考文献：
  名称：

  2-(N-甲酸甲酯-1,4,5,6-四氢吡啶-2-基)乙酸乙酯的高区域选择性合成及其通过不对称氢化转化为相应的(R)-乙基高吡啶甲酸酯

  摘要：

  摘要 以高区域选择性制备了具有内环双键的 2-(N-甲基甲酸-1,4,5,6-四氢吡啶-2-基)乙酸乙酯，并进一步还原成 (R)-N-保护的高哌啶酸，对映选择性良好。手性钌催化剂。

  DOI：

  10.1080/00397911003629457

文献信息

• Design, synthesis and cytotoxicity of the antitumor agent 1-azabicycles for chemoresistant glioblastoma cells
  作者：Mona Oliveira、Lourenço Luis Botelho de Santana、José Claudio Serafim、Airam Oliveira Santos、Michelle Pereira Quintino、José Tiago Menezes Correia、Fabiano Damasceno、José Ricardo Sabino、Thiago Rubens Cardim Pires、Paulo Lucas Cerqueira Coelho、Giselle Pinto de Faria Lopes、Henning Ulrich、Silvia Lima Costa、Silvio Cunha

  DOI：10.1007/s10637-019-00877-2

  日期：2020.10

  Twelve multi-functional pyrrolizidinones, indolizidinones and pyrroliazepinones were prepared from formal aza-[3 + 2] and aza-[3 + 3] cycloadditions of five- to seven-membered heterocyclic enaminones as diverse ambident electrophiles. The antitumor activity of these alkaloid-like compounds was investigated through an initial screening performed on human glioblastoma multiform (GBM) cell lines (GL-15, U251), on murine glioma cells line (C6) and on normal glial cells. Of the compounds tested, the new pyrrolo[1,2a]azepinone, [ethyl (3-oxo-1,2-diphenyl-6,7,8,9-tetrahydro-3H-pyrrolo[1,2a]azepin-9a(5H)-yl)acetate] or (Compound-13) exhibited selective cytotoxic effects on GBM-temozolomide resistant cells. Compound-13 exerted dose-dependent cytotoxic activity by promoting arrest of cells in the G0/G1 phase of the cell cycle in the first 24 h. The apoptotic effect observed was in a time-dependent manner. Anti-migratory effect promoted by the treatment with compound-13 was also observed. Moreover, healthy mixed glial cell cultures from rat brain exhibited no cytotoxicity effect upon exposure to compound-13. Thus, the present study paves the way for the use of compound-13 as novel antitumor scaffold candidate for glioma cell therapy.

  以五元至七元杂环烯酮作为不同的暧昧亲电体，通过正式的氮杂环合-[3 + 2]和氮杂环合-[3 + 3]环加成反应，制备了 12 种多功能吡咯烷酮、吲哚利嗪酮和吡咯并氮杂卓酮。通过对人类多形性胶质母细胞瘤（GBM）细胞系（GL-15、U251）、鼠胶质瘤细胞系（C6）和正常胶质细胞进行初步筛选，研究了这些生物碱类化合物的抗肿瘤活性。在测试的化合物中，新的吡咯并[1,2a]氮杂环庚酮[(3-氧代-1,2-二苯基-6,7,8,9-四氢-3H-吡咯并[1,2a]氮杂环庚-9a(5H)-基)乙酸乙酯]或（化合物-13）对 GBM-替莫唑胺耐药细胞具有选择性细胞毒性作用。化合物-13 具有剂量依赖性的细胞毒性活性，在细胞周期的前 24 h 促进细胞停滞在 G0/G1 期。观察到的凋亡效应与时间有关。化合物-13 还具有抗迁移作用。此外，来自大鼠大脑的健康混合胶质细胞培养物在暴露于化合物-13 后没有表现出细胞毒性效应。因此，本研究为将化合物-13 用作胶质瘤细胞治疗的新型抗肿瘤支架候选物铺平了道路。
• Tandem Transformations of Nitriles into N-Heterocyclic Compounds by Electrophilic Trapping of Blaise Reaction Intermediates
  作者：Hyunik Shin、Sang-gi Lee、Ju Kim、Yu Chun

  DOI：10.1055/s-0031-1290814

  日期：2012.6

  Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of omega-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of omega-chloroalkyl nitriles give N-fused indoles.
• Delbecq, Philippe; Bacos, Daniel; Celerier, Jean Pierre, Canadian Journal of Chemistry, 1991, vol. 69, # 8, p. 1201 - 1206
  作者：Delbecq, Philippe、Bacos, Daniel、Celerier, Jean Pierre、Lhommet, Gerard

  DOI：——

  日期：——
• Bacos, D.; Celerier, J. P.; Marx, E., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1387 - 1392
  作者：Bacos, D.、Celerier, J. P.、Marx, E.、Rosset, S.、Lhommet, G.

  DOI：——

  日期：——
• Brunerie, Pascal; Celerier, Jean-Pierre; Lhommet, Gerard, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 447 - 448
  作者：Brunerie, Pascal、Celerier, Jean-Pierre、Lhommet, Gerard

  DOI：——

  日期：——