trans 1,2,6-trimethyl-4-piperidone | 24506-51-2

• 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: trans 1,2,6-trimethyl-4-piperidone
• 英文别名: trans-1,2,6-trimethyl-4-piperidone；1,2,6-trimethylpiperidin-4-one；1,2,6-trimethylpiperid-4-one；(2R,6R)-1,2,6-trimethylpiperidin-4-one
• CAS: 24506-51-2；41248-68-4；114632-10-9
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: YHUNCTAOWLYFHG-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  trans 1,2,6-trimethyl-4-piperidone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以2.8 g的产率得到(2α,4β,6β)-1,2,6-trimethyl-4-piperidinol
  参考文献：
  名称：

  Structural analysis of 5-HT3 receptor antagonists: synthesis and pharmacological activity of various aromatic esters or amides derived from tropane and 1,2,6-trisubstituted piperidine

  摘要：

  Preliminary results of a structure-activity relationship in the field of 5-HT3 receptor antagonists on the influence of the aromatic ring and steric hindrance around the basic nitrogen atom are reported. The favorable role of the naphthalene moiety substituted by a carbonyl function in position 1 was demonstrated by measuring the biological activity using the inhibition of the specific binding of [H-3]BRL 43694 and the inhibition of the Bezold-Jarisch reflex. Several esters and amides of 1,2,6-trisubstituted piperidine derivatives with a suitable fit with the antagonist reference compounds were synthesized. The lack of biological activity of these compounds emphasizes the importance of steric hindrance for binding with the anionic receptor site. These data confirm the major role of the tropane and quinuclidine frameworks in the potency of a number of 5-HT3 antagonists.

  DOI：

  10.1016/0223-5234(93)90039-h
• 作为产物：
  描述：

  1,6-庚二烯-4-醇 在 chromium(VI) oxide 、 硫酸 、 叔丁胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 trans 1,2,6-trimethyl-4-piperidone
  参考文献：
  名称：

  Control of diastereoselectivity in the cyclization of dipropenyl ketone to 2,6-dimethyl-1-heterocyclo-hexan-4-one

  摘要：

  DOI：

  10.1007/bf01557515

文献信息

• [EN] TAM KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES TAM
  申请人：SYROS PHARMACEUTICALS INC

  公开号：WO2019014513A1

  公开（公告）日：2019-01-17

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions, and medicaments comprising such compounds, and methods of using such compounds to treat diseases, such as cancer.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物，以及利用这种化合物治疗疾病（如癌症）的方法。
• Studies on the stereochemistry of 1,2,6-trimethyl-4-piperidone
  作者：Florian Diwischek、Mario Arnone、Bernd Engels、Ulrike Holzgrabe

  DOI：10.1016/j.tet.2005.05.030

  日期：2005.7

  as well as conformational isomerism. Despite the symmetry of 1,2,6-trimethyl-4-piperidone two different sets of signals were present in the 1H and 13C NMR spectra. They were supposed to arise from a cis/trans mixture of 1,2,6-trimethyl-4-piperidone. In contrast to this explanation only two signals of the methyl groups and hydrogens at carbon atoms 2 and 6 were observed in the 1H and 13C NMR spectra,

  为了产生具有镇痛活性的螺哌啶的新衍生物，合成了1,2,6-三甲基-4-哌啶酮中间体。骨架的取代引起构型和构象异构现象。尽管1,2,6-三甲基-4-哌啶酮具有对称性，但在1 H和13 C NMR谱图中仍存在两组不同的信号。据推测它们是由1,2,6-三甲基-4-哌啶酮的顺式/反式混合物产生的。与该解释相反，在1 H和13 C NMR光谱中仅观察到碳原子2和6处的甲基和氢的两个信号，通常预期一个为顺式-另一个为两个反式异构体。为了解决这一差异，研究了导致1 H和13 C NMR光谱的1,2,6-三甲基-4-哌啶酮的异构体混合物。1,2,6-三甲基-4-哌啶酮的顺式和反式异构体的椅子构象之间的能量差与1,2,6-三甲基-反式异构体平衡过程的势能面通过量子化学计算确定其椅子构象异构体之间的4-哌啶酮。通过高温和低温NMR测量来测量平衡过程的势垒高度，以确认理论结果。所有调查的结果都很好地吻合，并证明是顺式的-/在室温下存在1
• Synthesis of Derivatives of 1, 2, 6-Trisubstttuted-4-Piperidones
  作者：Michel Langlois、Donglaï Yang、Jean-Louis Soulier、Claudie Florac

  DOI：10.1080/00397919209409262

  日期：1992.11

  Robinson-Schopf cyclisation was used to prepare several 1,2,6-trisubstituted-4-piperidones. 1,2,6-trimethyl-4-piperidone, tricyclic ketones 2 and 3 derivatives of coccinelline. In the case of 1,2,6-trimethyl-4-piperidone, a mixture of the trans and cis compounds 4 and 1 was obtained. The pure cis compound was prepared by another route.
• CASY A. F.; COATES J. E.; ROSTRON C., J. PHARM. AND PHARMACOL. <JPPM-AB>, 1976, 28, NO 2, 106-110
  作者：CASY A. F.、 COATES J. E.、 ROSTRON C.

  DOI：——

  日期：——
• KORSHEVETS I. A.; MISTRYUKOV EH. A., IZV. AN CCCP. CEP. XIM.,(1987) N 7, 1540-1545
  作者：KORSHEVETS I. A.、 MISTRYUKOV EH. A.

  DOI：——

  日期：——