1-(1-adamantyl)-N-ethenoxyethanimine | 1041846-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-adamantyl)-N-ethenoxyethanimine
• CAS: 1041846-07-4
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: QUIGUXUXFNPZMS-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  293.6±23.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(1-adamantyl)-N-ethenoxyethanimine 以 二甲基亚砜 为溶剂， 反应 1.0h， 以30%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 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 70.0 ℃ 、1.32 MPa 条件下， 反应 0.5h， 以80%的产率得到1-(1-adamantyl)-N-ethenoxyethanimine
  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