(E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-3-en-1-one | 23512-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-3-en-1-one
• 英文别名: (E)-5-(benzo[1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-3-en-1-one；trans-5-benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-pent-3-en-1-one；dihydropiperine；trans-Δ^β,γ-Dihydro-piperidin；Piperidine, 1-[(3E)-5-(1,3-benzodioxol-5-yl)-1-oxo-3-pentenyl]-；(E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpent-3-en-1-one
• CAS: 23512-55-2
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: MJBOPSKIWRUIBB-NSCUHMNNSA-N

物化性质

• 沸点：
  475.4±34.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)
• 保留指数：
  2601.8

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-3-en-1-one 、 2,2,6,6-四甲基哌啶氧化物 在 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到(E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pent-2-en-1-one
  参考文献：
  名称：

  TEMPO对β,γ-不饱和酰胺的化学选择性γ-氧化

  摘要：

  报道了一种用于 β,γ-不饱和酰胺的 γ-氧化的化学选择性和稳健的方案。在这种方法中，亲电酰胺活化（在罕见的不饱和酰胺应用中）能够与 TEMPO 进行区域选择性反应，从而产生标题产物。合成产物的自由基环化反应和氧化突出了所得产物的合成效用。

  DOI：

  10.1002/anie.202104023
• 作为产物：
  描述：

  胡椒碱 在 甲醇 、 magnesium 作用下， 反应 2.0h， 以96%的产率得到(E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-3-en-1-one
  参考文献：
  名称：

  使用 Mg/MeOH 将一些天然二烯酰胺转化为相应的 β, γ - 不饱和酰胺

  摘要：

  摘要 通过使用Mg/MeOH 将天然存在的二酰胺、胡椒碱、胡椒龙胺、guineensine、brachystamide-B 和pergumidiene 转化为相应的β, γ-不饱和酰胺。

  DOI：

  10.1080/00397919908086019

文献信息

• Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis
  作者：Mikael Pedersen、Bjørn Metzler、Gary Stafford、Johannes Van Staden、Anna Jäger、Hasse Rasmussen

  DOI：10.3390/molecules14093833

  日期：——

  Piper capense L.f. (Piperaceae) is used traditionally in South Africa as a sleep inducing remedy. Bioassay-guided fractionation of the roots of P. capense led to the isolation of piperine (1) and 4,5-dihydropiperine (2), which showed moderate affinity for the benzodiazepine site on the GABAA receptor (IC50 values of 1.2 mM and 1.0 mM, respectively). The present study suggests that strict structural properties of the amides are essential for affinity. Taken together, these observations suggest that the carbon chain must contain not less than four carbons, and that a conjugated double bond, adjacent to the amide group, is necessary for binding to the receptor and that the amine part should be bulky.

  Piper capense L.f.（胡椒科）在南非传统上被用作催眠药。P. capense根部的生物测定引导分离出白胡椒碱（piperine，1）和4,5-二氢白胡椒碱（4,5-dihydropiperine，2），它们对GABAA受体的苯二氮平位点表现出中等亲和力（IC50值分别为1.2 mM和1.0 mM）。本研究表明，酰胺的严格结构特性对于亲和力至关重要。综合这些观察结果表明，碳链必须至少含有四个碳原子，并且靠近酰胺基团的共轭双键对于与受体结合是必要的，同时胺部分应较为庞大。
• Homogeneous electro-mediated reduction of unsaturated compounds using Ni and Fe as mediators in DMF
  作者：Aderivaldo P. da Silva、Saulo D.C. Mota、Lothar W. Bieber、Marcelo Navarro

  DOI：10.1016/j.tet.2006.03.067

  日期：2006.6

  The homogeneous electro-mediated reduction (HEMR) of several organic compounds (cyclohexene, cyclohexanone, acetophenone, benzaldehyde, styrene, linalool, 1,3-cyclohexadiene, citral, trans-4-phenyl-3-buten-2-one, and piperine) was carried out using Fe2+, Ni2+, and [Ni-II(bpy)]Br-2 (bpy=2,2'-bipyridine) as electron mediators. An electrochemical system composed of sacrificial anode (Fe, Ni or Zn), nickel cathode, NaI (0.2 M) as supporting electrolyte in DMF and an undivided cell, was used. A constant current <= 100 mA was applied with a maximum cell potential of 2.0 V. Non-conjugated olefins are not reactive, but ketones may be easily reduced to the respective alcohol. In the case of conjugated olefins and ketones, [Ni-II(bpy)]Br-2 or Ni2+ mediator presented good reactivity and selectivity in most cases. Fe2+ more efficiently mediates the reduction of carbonyl containing systems. Preliminary electroanalytical studies indicate the complexation of the organic substrate by Fe2+ and Ni2+ ions and [Ni-II(bpy)]Br-2 complex. (c) 2006 Elsevier Ltd. All rights reserved.
• Transformation of the conjugated dienamide system of some natural alkamides to the β,γ-unsaturated amide function using
  作者：Biswanath Das、P Madhusudhan

  DOI：10.1016/s0040-4039(98)02005-x

  日期：1998.12

  The naturally occurring dienamides, piperine, piperlonguminine, guineensine, brachystamide-B and pergumidiene were converted to the corresponding beta, gamma-unsaturated amides by using Zn/HOAc. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Chemoselective γ‐Oxidation of β,γ‐Unsaturated Amides with TEMPO
  作者：Sebastian Heindl、Margaux Riomet、Ján Matyasovsky、Miran Lemmerer、Nicolas Malzer、Nuno Maulide

  DOI：10.1002/anie.202104023

  日期：2021.8.23

  A chemoselective and robust protocol for the γ-oxidation of β,γ-unsaturated amides is reported. In this method, electrophilic amide activation, in a rare application to unsaturated amides, enables a regioselective reaction with TEMPO resulting in the title products. Radical cyclisation reactions and oxidation of the synthesised products highlight the synthetic utility of the products obtained.

  报道了一种用于 β,γ-不饱和酰胺的 γ-氧化的化学选择性和稳健的方案。在这种方法中，亲电酰胺活化（在罕见的不饱和酰胺应用中）能够与 TEMPO 进行区域选择性反应，从而产生标题产物。合成产物的自由基环化反应和氧化突出了所得产物的合成效用。
• Conversion of some Natural Dienamides to the Corresponding β, γ - Unsaturated Amides using Mg/MeOH
  作者：Biswanath Das、A. Kashinatham、B. Venkataiah

  DOI：10.1080/00397919908086019

  日期：1999.11

  Abstract The naturally occurring dienamides, piperine, piperlonguminine, guineensine, brachystamide-B and pergumidiene were converted to the corresponding β, γ-unsaturated amides by using Mg/MeOH.

  摘要 通过使用Mg/MeOH 将天然存在的二酰胺、胡椒碱、胡椒龙胺、guineensine、brachystamide-B 和pergumidiene 转化为相应的β, γ-不饱和酰胺。