1-benzyloxycarbonyl-4-(3-phenylpropyl)piperazine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyloxycarbonyl-4-(3-phenylpropyl)piperazine
• 英文别名: Benzyl 4-(3-phenylpropyl)piperazine-1-carboxylate；benzyl 4-(3-phenylpropyl)piperazine-1-carboxylate
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: BQCMXWDJQFXKBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  肉桂基哌嗪 在 palladium on activated charcoal 、 乙二胺 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 24.0h， 生成 1-benzyloxycarbonyl-4-(3-phenylpropyl)piperazine
  参考文献：
  名称：

  Pd/C(en)-Catalyzed Chemoselective Hydrogenation with Retention of the N-Cbz Protective Group and its Scope and Limitations

  摘要：

  A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chemistry, especially in peptide synthesis (C) 2000 Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4020(00)00771-7

文献信息

• The Formation of a Novel Pd/C−Ethylenediamine Complex Catalyst:  Chemoselective Hydrogenation without Deprotection of the <i>O</i>-Benzyl and<i> N</i>-Cbz Groups
  作者：Hironao Sajiki、Kazuyuki Hattori、Kosaku Hirota

  DOI：10.1021/jo9814694

  日期：1998.10.1

  A Pd/C catalyst formed an isolable complex with ethylenediamine employed as the catalytic poison via one-to-one interaction between Pd metal and ethylenediamine, and this complex catalyst [Pd/C(en)] chemoselectively hydrogenated a variety of reducible functionalities such as olefin, acetylene, nitro, benzyl ester, and azido in the presence of an O-benzyl or N-Cbz protective group. These findings reinforce the versatility potential of O-benzyl and N-Cbz as protective groups in organic synthesis, and the Pd/C(en) catalyst has been identified as a novel and chemoselective catalyst for the hydrogenation.