1-[2-(3-methyl-2-butenyl)oxyethyl]-4-(3-methyl-2-butenyl)oxycarbonylpiperazine | 648910-22-9

• 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-methyl-2-butenyl)oxyethyl]-4-(3-methyl-2-butenyl)oxycarbonylpiperazine
• 英文别名: 3-Methylbut-2-enyl 4-[2-(3-methylbut-2-enoxy)ethyl]piperazine-1-carboxylate；3-methylbut-2-enyl 4-[2-(3-methylbut-2-enoxy)ethyl]piperazine-1-carboxylate
• CAS: 648910-22-9
• 化学式: C₁₇H₃₀N₂O₃
• 分子量: 310.437
• InChiKey: GSIMBMKCQZKJAW-UHFFFAOYSA-N

物化性质

• 沸点：
  397.6±42.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N-羟乙基哌嗪 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-[2-(3-methyl-2-butenyl)oxyethyl]-4-(3-methyl-2-butenyl)oxycarbonylpiperazine
  参考文献：
  名称：

  Prenyl carbamates: preparation and deprotection

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.03.028

文献信息

• 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.