4-((E)-3-Oxo-3-phenyl-propenyl)-piperidine-1-carboxylic acid tert-butyl ester | 291289-27-5

• 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: 4-((E)-3-Oxo-3-phenyl-propenyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: 1-(Tert-butoxycarbonyl)-4-(3-oxo-3-phenylprop-1-enyl)piperidine；tert-butyl 4-(3-oxo-3-phenylprop-1-enyl)piperidine-1-carboxylate
• CAS: 291289-27-5
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: XYJDXZJRFHANJE-UHFFFAOYSA-N

物化性质

• 沸点：
  429.6±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((E)-3-Oxo-3-phenyl-propenyl)-piperidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢氧化钾 、 草酰氯 、 氢气 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 生成 Methyl 2-{[3-({1-[(1,1-Dimethylethoxy)carbonyl]piperidin-4-yl}methyl)-2-phenylquinolin-4-yl]carbonyl}-1-phenylhydrazinecarboxylate
  参考文献：
  名称：

  N′,2-Diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists II

  摘要：

  Introduction of selected amine containing side chains into the 3-position of N',2-diphenylquinoline-4-carbohydrazide based NK3 antagonists abolishes unwanted hPXR activation. Introduction of a fluorine at the 8-position is necessary to minimize unwanted hIK(r) affinity and a piperazine N-tert-butyl group is necessary for metabolic stability. The lead compound (8m) occupies receptors within the CNS following oral dosing (Occ(90) 7 mg/kg po; plasma Occgo 0.4 mu M) and has good selectivity and excellent PK properties. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.085
• 作为产物：
  描述：

  在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-((E)-3-Oxo-3-phenyl-propenyl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  N′,2-Diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists II

  摘要：

  Introduction of selected amine containing side chains into the 3-position of N',2-diphenylquinoline-4-carbohydrazide based NK3 antagonists abolishes unwanted hPXR activation. Introduction of a fluorine at the 8-position is necessary to minimize unwanted hIK(r) affinity and a piperazine N-tert-butyl group is necessary for metabolic stability. The lead compound (8m) occupies receptors within the CNS following oral dosing (Occ(90) 7 mg/kg po; plasma Occgo 0.4 mu M) and has good selectivity and excellent PK properties. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.085

文献信息

• Quinoline derivatives as neurokinin receptor antagonists
  申请人：Carling William Robert

  公开号：US20090054440A1

  公开（公告）日：2009-02-26

  The present invention relates to substituted quinoline hydrazides of Formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , X, Y and Z are defined herein, pharmaceutical compositions comprising them and their use in treating diseases mediated by neurokinin-2 and/or neurokinin-3 (NK-3) receptors. These compounds can thus be used in methods of treatment to suppress and treat such disorders.

  本发明涉及式(I)所示的取代喹啉酰肼：其中R1、R2、R3、R4、R5、X、Y和Z在此定义，包含它们的药物组合物及其在治疗由神经激肽-2和/或神经激肽-3 (NK-3)受体介导的疾病中的用途。因此，这些化合物可用于治疗方法，以抑制和治疗这些疾病。
• Asymmetric Synthesis of P-Stereogenic Secondary Phosphine-Boranes by an Unsymmetric Bisphosphine Pincer-Nickel Complex
  作者：Chuanyong Wang、Kesheng Huang、Jie Ye、Wei-Liang Duan

  DOI：10.1021/jacs.1c02772

  日期：2021.4.21

  The first highly enantioselective catalytic synthesis of P-stereogenic secondary phosphine-boranes was realized by the asymmetric addition of primary phosphine to electron-deficient alkenes with a newly developed unsymmetric bisphosphine (PCP′) pincer-nickel complex. Various P-stereogenic secondary phosphine-boranes were obtained in 57–92% yields with up to 99% ee and >20:1 dr. The follow-up alkylation

  通过使用新开发的不对称双膦（PCP'）钳-镍络合物将伯膦不对称加成至缺电子烯烃中，实现了P-立体生成仲膦-硼烷的第一个高对映选择性催化合成。以57-92％的收率获得了各种P-立体异构仲膦-硼烷，ee高达99％，dr> 20：1。与烷基卤形成P–C键后的后续烷基化为获得具有不同官能团的P-手性化合物提供了一种实用的方法。
• Pyrrolidine modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US06399619B1

  公开（公告）日：2002-06-04

  The present invention is directed to pyrrolidine compounds of the formula I: (wherein R1, R2, R3, R4, R5, R6 and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及公式I的吡咯烷化合物：（其中R1，R2，R3，R4，R5，R6和n在此定义），该化合物可用作趋化因子受体活性的调节剂。特别地，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。
• US6399619B1
  申请人：——

  公开号：US6399619B1

  公开（公告）日：2002-06-04
• N′,2-Diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists II
  作者：Jason M. Elliott、Robert W. Carling、Gary G. Chicchi、James Crawforth、Peter H. Hutson、A. Brian Jones、Sarah Kelly、Rose Marwood、Georgina Meneses-Lorente、Elena Mezzogori、Fraser Murray、Michael Rigby、Inmaculada Royo、Michael G.N. Russell、Duncan Shaw、Bindi Sohal、Kwei Lan Tsao、Brian Williams

  DOI：10.1016/j.bmcl.2006.08.085

  日期：2006.11

  Introduction of selected amine containing side chains into the 3-position of N',2-diphenylquinoline-4-carbohydrazide based NK3 antagonists abolishes unwanted hPXR activation. Introduction of a fluorine at the 8-position is necessary to minimize unwanted hIK(r) affinity and a piperazine N-tert-butyl group is necessary for metabolic stability. The lead compound (8m) occupies receptors within the CNS following oral dosing (Occ(90) 7 mg/kg po; plasma Occgo 0.4 mu M) and has good selectivity and excellent PK properties. (c) 2006 Elsevier Ltd. All rights reserved.