1-piperidin-1-ylbutane-1,2-dione | 175346-60-8

• 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: 1-piperidin-1-ylbutane-1,2-dione
• 英文别名: piperidinyl 2-oxobutyramide
• CAS: 175346-60-8
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: CHLFINZCIMNMHA-UHFFFAOYSA-N

物化性质

• 沸点：
  259.1±23.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  溴代异丁烷 、 1-piperidin-1-ylbutane-1,2-dione 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以62%的产率得到2-hydroxy-4-methyl-1-piperidin-1-yl-2-vinylpentan-1-one
  参考文献：
  名称：

  Efficient Synthesis of Quaternary α-Hydroxy Acids by Alkylation of α-Ketoamide-Derived Dienediolates

  摘要：

  α-酮酰胺的两次脱质子化生成二烯二醇盐，它们经历区域选择性的α-烷基化反应，生成α-取代-α-羟基-β,γ-不饱和酰胺。生成的1,2-二取代烯烃仅为E-异构体。1,1-二取代和1,1,2-三取代烯烃也可以制备。这些酰胺可以容易地转化为相应的酸。

  DOI：

  10.1055/s-2005-918481
• 作为产物：
  描述：

  1-<(哌啶-1-基羰基)羰基>哌啶 、 乙基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.0h， 以88%的产率得到1-piperidin-1-ylbutane-1,2-dione
  参考文献：
  名称：

  Efficient Synthesis of Quaternary α-Hydroxy Acids by Alkylation of α-Ketoamide-Derived Dienediolates

  摘要：

  α-酮酰胺的两次脱质子化生成二烯二醇盐，它们经历区域选择性的α-烷基化反应，生成α-取代-α-羟基-β,γ-不饱和酰胺。生成的1,2-二取代烯烃仅为E-异构体。1,1-二取代和1,1,2-三取代烯烃也可以制备。这些酰胺可以容易地转化为相应的酸。

  DOI：

  10.1055/s-2005-918481

文献信息

• Electrophile-Directed Diastereoselective Alkylation of Prochiral Enediolates
  作者：Stephen P. Marsden、Rebecca Newton

  DOI：10.1021/ja073624e

  日期：2007.10.1

  Prochiral substituted enediolates undergo diastereoselective alkylation with β-chiral primary iodohydrin derivatives, with selectivities up to 97:3. The most selective reactions occur with dienediolates, but reasonable selectivities can also be obtained with alkyl- and aryl-substituted enediolates. The presence of the lithioalkoxy substituent on the enolate is crucial for selectivity, as is the presence

  前手性取代的烯二醇与 β-手性伯碘醇衍生物进行非对映选择性烷基化，选择性高达 97:3。选择性最强的反应发生在二烯二醇酯上，但使用烷基和芳基取代的烯二醇酯也可以获得合理的选择性。烯醇化物上锂硫代烷氧基取代基的存在对选择性至关重要，正如亲电试剂中β-氧的存在一样，导致烷基化是通过亲核试剂和亲电试剂的锂配位组装发生的。该反应也适用于手性二级保护碘醇，从而有效构建连续的四级和三级不对称中心。
• C-Met Modulators and Method of Use
  申请人：Bannen Lynne Canne

  公开号：US20110077233A1

  公开（公告）日：2011-03-31

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. More specifically, the invention provides quinazolines and quinolines which inhibit, regulate, and/or modulate kinase receptor, particularly c-Met, KDF, c-Kit, flt-3 and flt-4, signal transduction pathways related to the changes in cellular activities as mentioned above, compositions which contain these compounds, and methods of using them to treat kinase-dependent diseases and conditions. The present invention also provides methods for making compounds as mentioned above, and compositions which contain these compounds.

  本发明提供了用于调节蛋白激酶酶活性以调节细胞活动（如增殖、分化、程序性细胞死亡、迁移和化学侵袭）的化合物。更具体地，本发明提供了能够抑制、调节和/或调节激酶受体（特别是c-Met、KDF、c-Kit、flt-3和flt-4）信号转导通路的喹唑啉和喹啉，这些信号转导通路与上述细胞活动的变化有关，以及包含这些化合物的组合物和使用它们治疗激酶依赖性疾病和病况的方法。本发明还提供了制备上述化合物的方法和包含这些化合物的组合物。
• Nitrogen and Sulfur-Containing Heterocycle Derivatives
  申请人：Armilli Murty N.

  公开号：US20110269953A1

  公开（公告）日：2011-11-03

  The present invention provides nitrogen and sulfur-containing heterocycle compounds to be used as scaffolds and, in particular, nitrogen and sulfur-containing heterocycle compounds having a thiomorpholine core. The compounds herein described may be useful in treating diseases such as diabetes, obesity, cancer, cardiovascular, Alzheimer's, inflammatory, antidepressant, rheumatoid arthritis, multiple sclerosis, allergic rhinitis, asthma as well as viral and bacterial infections. The compounds herein described may also be useful in treating CNS disorders such as but not limited to Schizophrenia, Alzheimer's disease (AD).

  本发明提供了氮和硫含杂环化合物，用作支架，特别是具有硫代吗啉核心的氮和硫含杂环化合物。所述化合物可用于治疗糖尿病、肥胖症、癌症、心血管疾病、阿尔茨海默病、炎症、抗抑郁症、类风湿性关节炎、多发性硬化症、过敏性鼻炎、哮喘以及病毒和细菌感染等疾病。所述化合物还可用于治疗中枢神经系统疾病，例如但不限于精神分裂症、阿尔茨海默病（AD）。
• c-Met Modulators and Method of Use
  申请人：Exelixis, Inc.

  公开号：US20140155378A9

  公开（公告）日：2014-06-05

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. More specifically, the invention provides quinazolines and quinolines which inhibit, regulate, and/or modulate kinase receptor, particularly c-Met, KDF, c-Kit, flt-3 and flt-4, signal transduction pathways related to the changes in cellular activities as mentioned above, compositions which contain these compounds, and methods of using them to treat kinase-dependent diseases and conditions. The present invention also provides methods for making compounds as mentioned above, and compositions which contain these compounds.

  本发明提供了用于调节蛋白激酶酶活性以调节细胞活动（如增殖、分化、程序性细胞死亡、迁移和化学入侵）的化合物。更具体地，本发明提供了能够抑制、调节和/或调节激酶受体（特别是c-Met、KDF、c-Kit、flt-3和flt-4）信号转导通路的喹唑啉和喹啉，这些通路与上述细胞活动的变化有关，以及含有这些化合物的组合物和使用它们治疗激酶依赖性疾病和病况的方法。本发明还提供了制备上述化合物的方法和含有这些化合物的组合物。
• C-Met Modulators and Methods of Use
  申请人：Exelixis, Inc.

  公开号：US20150376133A1

  公开（公告）日：2015-12-31

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. More specifically, the invention provides quinazolines and quinolines which inhibit, regulate and/or modulate kinase receptor, particularly c-Met, KDR, c-Kit, flt-3 and flt-4, signal transduction pathways related to the changes in cellular activities as mentioned above, compositions which contain these compounds, and methods of using them to treat kinase-dependent diseases and conditions. The present invention also provides methods for making compounds as mentioned above, and compositions which contain these compounds.

  本发明提供了一种调节蛋白激酶酶活性以调节细胞活动（如增殖、分化、程序性细胞死亡、迁移和化学侵袭）的化合物。更具体地，本发明提供了能够抑制、调节和/或调节激酶受体（特别是c-Met、KDR、c-Kit、flt-3和flt-4）信号转导通路，从而影响上述细胞活动变化的喹唑啉和喹啉，以及含有这些化合物的组合物和使用它们治疗激酶依赖性疾病和病况的方法。本发明还提供了制备上述化合物的方法和含有这些化合物的组合物。