2-(1-金刚烷基)-1-乙烯基吡咯 | 1041846-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-(1-金刚烷基)-1-乙烯基吡咯
• 英文名称: 2-(1-adamantyl)-1-vinylpyrrole
• 英文别名: 2-(1-Adamantyl)-1-ethenylpyrrole；2-(1-adamantyl)-1-ethenylpyrrole
• CAS: 1041846-06-3
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: VDOQYDHBSJLKBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(1-金刚烷基)-1-乙烯基吡咯 在 mercury(II) diacetate 、 sodium tetrahydroborate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.67h， 以77%的产率得到2-(金刚烷-1-基)-1H-吡咯
  参考文献：
  名称：

  A short-cut from 1-acetyl adamantane to 2-(1-adamantyl)pyrroles

  摘要：

  The oxime of 1-acetyl adamantane 2 is added to acetylene (KOH/DMSO, 70 degrees C, initial acetylene pressure 13 atm, 30 min) to afford the Corresponding O-vinyl oxime 5 in 80% yield. The latter upon heating (DMSO, 120 degrees C, 1 h) gives 2-(1-adamantyl)pyrrole 3, 1-acetyl adamantane 1, and adamantane (6:31 mass ratio), the yield of the pyrrole 3 being 83% (based on 1-acetyl adamantane 1 consumed). Under harsher conditions (NaOH/DMSO, 130 degrees C, atmospheric pressure of acetylene, 4 h) oxime 2 reacts with acetylene to furnish pyrrole 3, 1-acetyl adamantane 1, 1-vinyl adamantane 9, and adamantane (6:7:3:1 mass ratio), with the isolated yield of pyrrole 3 reaching 34%. Under pressure (NaOH/DMSO, 120 degrees C, initial acetylene pressure 14 atm, 1 h) the same reaction leads to 2-(1-adamantyl)-1-vinylpyrrole 4 and ketone 1 in 48% (based on consumed ketone 1) and 24% yields, respectively. The pyrrole 4 is easily deprotected to the corresponding 1H-pyrrole 3 in 77% yield by treatment (aqueous MeCN) with Hg(OAc)(2) and NaBH4. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.023
• 作为产物：
  描述：

  1-adamantane methyl ketone oxime 、 乙炔 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 80.0~120.0 ℃ 、1.42 MPa 条件下， 反应 1.0h， 以0.44 g的产率得到2-(1-金刚烷基)-1-乙烯基吡咯
  参考文献：
  名称：

  A short-cut from 1-acetyl adamantane to 2-(1-adamantyl)pyrroles

  摘要：

  The oxime of 1-acetyl adamantane 2 is added to acetylene (KOH/DMSO, 70 degrees C, initial acetylene pressure 13 atm, 30 min) to afford the Corresponding O-vinyl oxime 5 in 80% yield. The latter upon heating (DMSO, 120 degrees C, 1 h) gives 2-(1-adamantyl)pyrrole 3, 1-acetyl adamantane 1, and adamantane (6:31 mass ratio), the yield of the pyrrole 3 being 83% (based on 1-acetyl adamantane 1 consumed). Under harsher conditions (NaOH/DMSO, 130 degrees C, atmospheric pressure of acetylene, 4 h) oxime 2 reacts with acetylene to furnish pyrrole 3, 1-acetyl adamantane 1, 1-vinyl adamantane 9, and adamantane (6:7:3:1 mass ratio), with the isolated yield of pyrrole 3 reaching 34%. Under pressure (NaOH/DMSO, 120 degrees C, initial acetylene pressure 14 atm, 1 h) the same reaction leads to 2-(1-adamantyl)-1-vinylpyrrole 4 and ketone 1 in 48% (based on consumed ketone 1) and 24% yields, respectively. The pyrrole 4 is easily deprotected to the corresponding 1H-pyrrole 3 in 77% yield by treatment (aqueous MeCN) with Hg(OAc)(2) and NaBH4. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.023

文献信息

• A short-cut from 1-acetyl adamantane to 2-(1-adamantyl)pyrroles
  作者：Boris A. Trofimov、Elena Yu. Schmidt、Nadezhda V. Zorina、Elena Yu. Senotrusova、Nadezhda I. Protsuk、Igor A. Ushakov、Al’bina I. Mikhaleva、Rachel Méallet-Renault、Gilles Clavier

  DOI：10.1016/j.tetlet.2008.05.023

  日期：2008.7

  The oxime of 1-acetyl adamantane 2 is added to acetylene (KOH/DMSO, 70 degrees C, initial acetylene pressure 13 atm, 30 min) to afford the Corresponding O-vinyl oxime 5 in 80% yield. The latter upon heating (DMSO, 120 degrees C, 1 h) gives 2-(1-adamantyl)pyrrole 3, 1-acetyl adamantane 1, and adamantane (6:31 mass ratio), the yield of the pyrrole 3 being 83% (based on 1-acetyl adamantane 1 consumed). Under harsher conditions (NaOH/DMSO, 130 degrees C, atmospheric pressure of acetylene, 4 h) oxime 2 reacts with acetylene to furnish pyrrole 3, 1-acetyl adamantane 1, 1-vinyl adamantane 9, and adamantane (6:7:3:1 mass ratio), with the isolated yield of pyrrole 3 reaching 34%. Under pressure (NaOH/DMSO, 120 degrees C, initial acetylene pressure 14 atm, 1 h) the same reaction leads to 2-(1-adamantyl)-1-vinylpyrrole 4 and ketone 1 in 48% (based on consumed ketone 1) and 24% yields, respectively. The pyrrole 4 is easily deprotected to the corresponding 1H-pyrrole 3 in 77% yield by treatment (aqueous MeCN) with Hg(OAc)(2) and NaBH4. (C) 2008 Elsevier Ltd. All rights reserved.