[(2S)-1-methylpiperidin-2-yl]methanone | 852324-34-6

• 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: [(2S)-1-methylpiperidin-2-yl]methanone
• 英文别名: (2S)-1-methylpiperidine-2-carbaldehyde
• CAS: 852324-34-6
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: HBQKERHWQDYYEM-ZETCQYMHSA-N

物化性质

• 沸点：
  173.1±33.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(2S)-1-methylpiperidin-2-yl]methanone 在 氢气 作用下， 生成 (S)-N-Methyl-2-(3'-phenylpropyl)piperidine
  参考文献：
  名称：

  Alkylation of 2-lithio-N-methylpiperidines and -pyrrolidines: scope, limitations, and stereochemistry

  摘要：

  The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating. With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases. Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products. A mechanistic interpretation is presented.

  DOI：

  10.1021/jo00123a008
• 作为产物：
  描述：

  (R)-N-Methyl-2-(tributylstannyl)piperidine 在 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 为溶剂， 反应 3.33h， 生成 [(2S)-1-methylpiperidin-2-yl]methanone
  参考文献：
  名称：

  Alkylation of 2-lithio-N-methylpiperidines and -pyrrolidines: scope, limitations, and stereochemistry

  摘要：

  The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating. With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases. Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products. A mechanistic interpretation is presented.

  DOI：

  10.1021/jo00123a008

文献信息

• COMPOUNDS AND METHODS FOR ANTIVIRAL TREATMENT
  申请人：GILEAD SCIENCES, INC.

  公开号：US20130273037A1

  公开（公告）日：2013-10-17

  Compounds and pharmaceutically acceptable salts and esters and compositions thereof, for treating viral infections are provided. The compounds and compositions are useful for treating Pneumovirinae virus infections. The compounds, compositions, and methods provided are particularly useful for the treatment of Human respiratory syncytial virus infections.

  提供用于治疗病毒感染的化合物、药用可接受的盐和酯及其组合物。这些化合物和组合物对于治疗Pneumovirinae病毒感染很有用。提供的化合物、组合物和方法特别适用于治疗人类呼吸道合胞病毒感染。
• Pyrrolopyridine kinase inhibiting compounds
  申请人：Dong Han-Qing

  公开号：US20070129364A1

  公开（公告）日：2007-06-07

  Compounds represented by Formula (I): or stereoisomers or pharmaceutically acceptable salts thereof, are inhibitors of least one of the Abl, Aurora-A, Blk, c-Raf, cSRC, Src, PRK2, FGFR3, Flt3, Lck, Mek1, PDK-1, GSK3β, EGFR, p70S6K, BMX, SGK, CaMKII, Tie-2, IGF-1R, Ron, Met, and KDR kinases in animals, including humans, for the treatment and/or prevention of various diseases and conditions such as cancer.

  由式（I）表示的化合物或其立体异构体或其药用可接受的盐，是对动物中至少一种Abl、Aurora-A、Blk、c-Raf、cSRC、Src、PRK2、FGFR3、Flt3、Lck、Mek1、PDK-1、GSK3β、EGFR、p70S6K、BMX、SGK、CaMKII、Tie-2、IGF-1R、Ron、Met和KDR激酶的抑制剂，包括人类，用于治疗和/或预防癌症等各种疾病和病况。
• INHIBITORS OF JNK
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2283009B1

  公开（公告）日：2012-08-29
• US8980878B2
  申请人：——

  公开号：US8980878B2

  公开（公告）日：2015-03-17
• US9504689B2
  申请人：——

  公开号：US9504689B2

  公开（公告）日：2016-11-29