1-甲基-3-(3-氧代-1,3-二苯基丙基)哌啶-4-酮 | 68164-52-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1-甲基-3-(3-氧代-1,3-二苯基丙基)哌啶-4-酮
• 英文名称: 1-methyl-3-(3-oxo-1,3-diphenylpropyl)piperidin-4-one
• CAS: 68164-52-3
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: PPDGTLXAPHOARD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-3-(3-氧代-1,3-二苯基丙基)哌啶-4-酮 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以60%的产率得到6-methyl-2,4-diphenyl-5,6,7,8-tetrahydro-1,6-naphthyridine
  参考文献：
  名称：

  5,6,7,8-四氢-1,6-萘啶新衍生物的合成及其药理特性

  摘要：

  摘要 研究了哌啶和托烷的1,5-二羰基衍生物与盐酸羟胺的杂环化反应。获得的所有 5,6,7,8-四氢-1,6-萘啶均表现出明显的镇痛作用。

  DOI：

  10.1007/s11172-005-0247-y
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 反式-查耳酮 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以24%的产率得到1-甲基-3-(3-氧代-1,3-二苯基丙基)哌啶-4-酮
  参考文献：
  名称：

  1,2,5-trimethylpiperidin-4-one 与查耳酮反应的区域和立体化学特征

  摘要：

  研究了 N-取代的哌啶-4-酮与亚苄基苯乙酮的反应，导致了许多杂环 1,5-二羰基化合物的合成。1,2,5-Trimethylpiperidin-4-one 进入级联型查耳酮加成，伴随分子内醛醇缩合产生 3-氮杂双环 [3.3.1] 壬烷系统。确定了合成的1,5-二羰基化合物和氮杂双环壬烷的构象；研究了 1,2,5-trimethylpiperidin-4-one 与查耳酮反应的区域和立体化学特征。

  DOI：

  10.1007/s11172-005-0194-7

文献信息

• Direct Asymmetric Michael Additions of Ketones to Nitroolefins and Chalcones Catalyzed by a Chiral C2-Symmetric Pyrrolidine-based Tetraamine
  作者：Shijun Ma、Lulu Wu、Ming Liu、Yongmei Wang

  DOI：10.1002/cjoc.201200214

  日期：2012.8.14

  C2‐Symmetric pyrrolidine‐based tetraamine, available from commercially starting materials, showed good catalytic activity for asymmetric Michael additions of ketones to nitroalkenes especially to chalcones. The reactions proceeded to give the corresponding products in good yields and in a highly selective manner.

  C 2对称的基于吡咯烷的四胺（可从商业原料获得）显示出良好的催化活性，可将酮不​​对称地迈克尔加成至硝基烯烃，特别是对查耳酮。反应进行以高收率和高度选择性的方式得到相应的产物。
• Pyrrolidine–pyridine base catalysts for the enantioselective Michael addition of ketones to chalcones
  作者：Da-Zhen Xu、Sen Shi、Yingjun Liu、Yongmei Wang

  DOI：10.1016/j.tet.2009.09.001

  日期：2009.11

  A series of pyrrolidine-pyridine base organocatalysts have been developed and 3a found to be a highly effective catalyst for the asymmetric Michael addition reactions of ketones to chalcones. The reaction generated the corresponding products 1, 5-diketones in excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 100% ee). (c) 2009 Elsevier Ltd. All rights reserved.
• Direct asymmetric Michael addition of ketones to chalcones catalyzed by a hydroxyphthalimide derived triazole–pyrrolidine
  作者：Togapur Pavan Kumar、Mohammad Abdul Sattar、Vanka Uma Maheshwara Sarma

  DOI：10.1016/j.tetasy.2013.11.002

  日期：2013.12

  An efficient protocol for the enantioselective Michael additions of ketones to chalcones catalyzed by a hydroxyphthalimide linked triazole-pyrrolidine derivative has been developed. The corresponding products, 1,5-dicarbonyl compounds, were obtained in good yields with high levels of stereoselectivities under mild reaction conditions employing benzoic acid as an additive. (C) 2013 Elsevier Ltd. All rights reserved.
• Regio- and stereochemical features of the reactions of 1,2,5-trimethylpiperidin-4-one with chalcone
  作者：S. Z. Vatsadze、M. L. Kostochka、V. P. Lezina、V. G. Vinokurov、N. V. Zyk

  DOI：10.1007/s11172-005-0194-7

  日期：2004.12

  The reactions of N-substituted piperidin-4-ones with benzylideneacetophenone, resulting in the synthesis of a number of heterocyclic 1,5-dicarbonyl compounds, were studied. 1,2,5-Trimethylpiperidin-4-one enters into cascade-type chalcone addition accompanied by intramolecular aldol condensation giving rise to the 3-azabicyclo[3.3.1]nonane system. The conformations of the 1,5-dicarbonyl compounds and

  研究了 N-取代的哌啶-4-酮与亚苄基苯乙酮的反应，导致了许多杂环 1,5-二羰基化合物的合成。1,2,5-Trimethylpiperidin-4-one 进入级联型查耳酮加成，伴随分子内醛醇缩合产生 3-氮杂双环 [3.3.1] 壬烷系统。确定了合成的1,5-二羰基化合物和氮杂双环壬烷的构象；研究了 1,2,5-trimethylpiperidin-4-one 与查耳酮反应的区域和立体化学特征。
• Synthesis of new derivatives of 5,6,7,8-tetrahydro-1,6-naphthyridines and their pharmacological properties
  作者：S. Z. Vatsadze、M. L. Kostochka、V. P. Lezina、V. G. Vinokurov、P. M. Klodt、N. V. Zyk

  DOI：10.1007/s11172-005-0247-y

  日期：2005.1

  Abstract1,5-Dicarbonyl derivatives of piperidine and tropane were studied in the heterocyclization with hydroxylamine hydrochloride. All the 5,6,7,8-tetrahydro-1,6-naphthyridines obtained exhibit a pronounced analgesic effect.

  摘要 研究了哌啶和托烷的1,5-二羰基衍生物与盐酸羟胺的杂环化反应。获得的所有 5,6,7,8-四氢-1,6-萘啶均表现出明显的镇痛作用。