1-[2-(3-methylbut-2-enyloxy)ethyl]piperazine | 648910-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-[2-(3-methylbut-2-enyloxy)ethyl]piperazine
• 英文别名: 1-[2-(3-methyl-2-butenyl)oxyethyl]piperazine；1-{2-[(3-Methylbut-2-en-1-yl)oxy]ethyl}piperazine；1-[2-(3-methylbut-2-enoxy)ethyl]piperazine
• CAS: 648910-29-6
• 化学式: C₁₁H₂₂N₂O
• 分子量: 198.308
• InChiKey: IUZKMLXVJOVLKY-UHFFFAOYSA-N

物化性质

• 沸点：
  283.2±25.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[2-(3-methyl-2-butenyl)oxyethyl]-4-(3-methyl-2-butenyl)oxycarbonylpiperazine 在 碘 、 锌 作用下， 以 甲醇 为溶剂， 反应 7.5h， 以63%的产率得到1-[2-(3-methylbut-2-enyloxy)ethyl]piperazine
  参考文献：
  名称：

  One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc

  摘要：

  The prenyloxycarbonyl (Preoc) moiety was efficiently removed from carbamates to provide the corresponding amines in good to excellent yields (63-88%) by using iodine in methanol followed by treatment of the resulting beta-methoxyiodides by zinc powder. The reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic methyl ethers. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.058

文献信息

• Thiyl Radical-Mediated Cleavage of Allylic C−N Bonds: Scope, Limitations, and Theoretical Support to the Mechanism
  作者：Stéphanie Escoubet、Stéphane Gastaldi、Vitaliy I. Timokhin、Michèle P. Bertrand、Didier Siri

  DOI：10.1021/ja049859x

  日期：2004.10.1

  Thiols mediate the radical isomerization of allylic amines into enamines. The reaction results in the cleavage of the allylic C-N bond, after treatment with aqueous HCl. The mechanism involves the abstraction of an allylic hydrogen alpha to nitrogen by thiyl radical, followed by a return hydrogen transfer from the thiol to the carbon gamma to nitrogen in the intermediate allylic radical. The scope and

  硫醇介导烯丙胺自由基异构化为烯胺。在用 HCl 水溶液处理后，该反应导致烯丙基 CN 键断裂。该机制涉及通过硫基自由基将氮的烯丙基氢 α 提取出来，然后将氢从硫醇返回到碳 γ 到中间烯丙基中的氮。研究了与硫醇的性质、烯丙基链的结构和氮上取代基的性质有关的反应范围和限制。实验结果的解释依据是起始烯丙胺中 C-Halpha BDE 和所得烯胺中 C-Hgamma BDE 的 DFT 计算。初始氢转移的效率是反应进行的首要条件。必须在 SH BDE 和上述两种 CH BDE 之间找到平衡。通过对起始烯丙基胺的优化几何形状进行的 NBO 计算来分析立体电子因素的发生率。为了通过 p-TolS(*) 从烯丙基和异戊二烯衍生物中提取 Halpha，进行了过渡结构的额外计算和随后的反应曲线追踪。后者使我们能够估计硫自由基从 N-异戊二烯胺和 N-烯丙胺中提取氢的速率常数。通过对起始烯丙基胺的优化几何形状进行的
• One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tetlet.2003.10.058

  日期：2003.12

  The prenyloxycarbonyl (Preoc) moiety was efficiently removed from carbamates to provide the corresponding amines in good to excellent yields (63-88%) by using iodine in methanol followed by treatment of the resulting beta-methoxyiodides by zinc powder. The reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic methyl ethers. (C) 2003 Elsevier Ltd. All rights reserved.
• Prenyl carbamates: preparation and deprotection
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tet.2004.03.028

  日期：2004.5

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.