cis-5-benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-pent-3-en-1-one

• 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: cis-5-benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-pent-3-en-1-one
• 英文别名: Piperidine, 1-[(3Z)-5-(1,3-benzodioxol-5-yl)-1-oxo-3-pentenyl]-；(Z)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpent-3-en-1-one
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: MJBOPSKIWRUIBB-IHWYPQMZSA-N

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

• 作为产物：
  描述：

  胡椒碱 在 (2,2'-联吡啶)二溴化镍(II) 1,2-二溴乙烷 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以80%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：

  Homogeneous electro-mediated reduction of unsaturated compounds using Ni and Fe as mediators in DMF

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.03.067

文献信息

• 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.
• 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.