1-甲基哌啶-2,3-二酮 | 30932-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-甲基哌啶-2,3-二酮
• 英文名称: 1-methylpiperidine-2,3-dione
• 英文别名: 1-Methyl-2,3-piperidindion
• CAS: 30932-82-2
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: NNDFUMFEKPCADK-UHFFFAOYSA-N

物化性质

• 沸点：
  199.7±23.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基哌啶-2,3-二酮 在 甲酸 作用下， 反应 0.5h， 生成 2,3,4,9-四氢-2-甲基-1H-吡啶并[3,4-b]吲哚-1-酮
  参考文献：
  名称：

  Herdeis, Claus; Dimmerling, Anna, Heterocycles, 1984, vol. 22, # 10, p. 2277 - 2283

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基哌啶 在 碘苯二乙酸 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以62%的产率得到1-甲基哌啶-2,3-二酮
  参考文献：
  名称：

  PIDA/I₂-Mediated α- and β-C(sp³)–H Bond Dual Functionalization of Tertiary Amines

  摘要：

  The alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines is still a challenging task for both organic and medicinal chemists. Herein a direct, mild, metal-free, and site-specific method mediated by PIDA/I-2 was developed for alpha,beta-C(sp(3))-H bond dual functionalization of tertiary amines, and this method can provide facile access to alpha-keto lactams or rarely studied alpha,alpha-diiodo lactams. Moreover, this method was used for the effective syntheses of three natural products [obscurumine C (13), obscurumine O (17), and strychnocarpine (18)] and direct preparation of mimics of the in vivo metabolites of two FDA-approved drugs (imatinib and donepezil) in 36-60% overall yield. The method represents a promising protocol for the late-stage alpha,beta-C(sp(3))-H bond oxidative dual functionalization of tertiary amine-containing drugs and complex natural products.

  DOI：

  10.1021/acs.joc.8b01424

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE<br/>[FR] INHIBITEURS À PETITE MOLÉCULE DE KINASE INDUISANT NF-KB
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2020239999A1

  公开（公告）日：2020-12-03

  The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.

  本发明涉及抑制NIK的化合物，以及包含这些化合物的药物组合物和使用方法。这些化合物和药物组合物预期能用于预防或治疗癌症（如包括白血病、淋巴瘤和多发性骨髓瘤的B细胞恶性肿瘤）、炎症性疾病、自身免疫疾病、免疫皮肤病学疾病（如掌跖脓疱病和化脓性汗腺炎）以及代谢紊乱疾病（如肥胖和糖尿病）。
• 6,5-HETEROCYCLIC PROPARGYLIC ALCOHOL COMPOUNDS AND USES THEREFOR
  申请人：Staben Steven

  公开号：US20120214762A1

  公开（公告）日：2012-08-23

  The invention relates to novel compounds of Formula I: wherein A, Y, R 1 , R 2 and the subscript b each has the meaning as described herein and compounds of Formula I, and stereoisomers, geometric isomers, tautomers, solvates, metabolites, isotopes, pharmaceutically acceptable salts, or prodrugs thereof. Compounds of Formula I and pharmaceutical compositions thereof are useful in the treatment of disease and disorders in which undesired or over-activation of NF-kB signaling is observed.

  这项发明涉及公式I的新化合物： 其中A、Y、R1、R2和下标b各自具有如本文所述的含义，以及公式I的化合物、立体异构体、几何异构体、互变异构体、溶剂合物、代谢物、同位素、药学上可接受的盐或其前药。公式I的化合物及其药物组成物在治疗观察到NF-kB信号通路的不良或过度激活的疾病和紊乱中是有用的。
• [EN] SMALL MOLECULE INHIBITORS OF NF-KB INDUCING KINASE<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE KINASE INDUISANT NF-KB
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2022104348A1

  公开（公告）日：2022-05-19

  This invention relates to compounds of Formula I that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.

  本发明涉及公式I的化合物，其抑制NIK，以及包含这种化合物的制药组合物和使用它们的方法。这些化合物和制药组合物有助于预防或治疗癌症（如B细胞恶性肿瘤，包括白血病，淋巴瘤和骨髓瘤），炎症性疾病，自身免疫性疾病，免疫性皮肤病，如掌跖症和汗腺炎，以及代谢性疾病，如肥胖和糖尿病。
• 6,5-Heterocyclic Propargylic Alcohol Compounds and Uses Therefor
  申请人：Genentech, Inc.

  公开号：US20150038460A1

  公开（公告）日：2015-02-05

  The invention relates to novel compounds of Formula I: wherein A, Y, R 1 , R 2 and the subscript b each has the meaning as described herein and compounds of Formula I, and stereoisomers, geometric isomers, tautomers, solvates, metabolites, isotopes, pharmaceutically acceptable salts, or prodrugs thereof. Compounds of Formula I and pharmaceutical compositions thereof are useful in the treatment of disease and disorders in which undesired or over-activation of NF-kB signaling is observed.

  该发明涉及公式I的新化合物：其中A，Y，R1，R2和下标b各自具有如下所述的含义，以及公式I的化合物，立体异构体，几何异构体，互变异构体，溶剂化物，代谢物，同位素，药学上可接受的盐或其前药。公式I的化合物及其制药组合物在治疗疾病和障碍方面有用，其中观察到NF-kB信号不良或过度激活。
• 6,5-heterocyclic propargylic alcohol compounds and uses therefor
  申请人：Staben Steven

  公开号：US08901313B2

  公开（公告）日：2014-12-02

  The invention relates to novel compounds of Formula I: wherein A, Y, R1, R2 and the subscript b each has the meaning as described herein and compounds of Formula I, and stereoisomers, geometric isomers, tautomers, solvates, metabolites, isotopes, pharmaceutically acceptable salts, or prodrugs thereof. Compounds of Formula I and pharmaceutical compositions thereof are useful in the treatment of disease and disorders in which undesired or over-activation of NF-kB signaling is observed.

  本发明涉及一种新型化合物I的公式：其中A，Y，R1，R2和下标b具有如下所述的含义，以及化合物I的立体异构体，几何异构体，互变异构体，溶剂化物，代谢物，同位素，药学上可接受的盐或其前药。公式I化合物及其制药组合物在治疗疾病和障碍方面有用，其中观察到NF-kB信号的不良或过度激活。