(+/-)-3-ethyl-3-allyl-2-piperidone | 381726-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+/-)-3-ethyl-3-allyl-2-piperidone
• 英文别名: 3-allyl-3-ethylpiperidin-2-one；3-Ethyl-3-prop-2-enylpiperidin-2-one
• CAS: 381726-11-0
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: IFOBDRGKVICYEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-3-ethyl-3-allyl-2-piperidone 在 镍 氢氧化钾 、 硼烷四氢呋喃络合物 、 五氯化磷 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 三氧化硫吡啶 、 silver nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 100.0 ℃ 、137.9 kPa 条件下， 反应 14.0h， 生成 rhazinilam
  参考文献：
  名称：

  Concise synthesis of (±)-rhazinilam

  摘要：

  2-Piperidone has been converted into (+/-)-rhazinilam in nine steps in 8% overall yield. The key transformation involves the conversion of the lactam 5 into the annulated pyrrole derivative 3 via the thiophenyl imine 8. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00859-6
• 作为产物：
  描述：

  3-Ethyl-1-[(4-nitrophenyl)methyl]-3-prop-2-enylpiperidin-2-one 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以55%的产率得到(+/-)-3-ethyl-3-allyl-2-piperidone
  参考文献：
  名称：

  A new method for the cleavage of nitrobenzyl amides and ethers

  摘要：

  A mild and efficient o- and p-nitrobenzyl cleavage protocol was developed. o- and p-nitrobenzyl groups were easily removed from a variety of substrates using 20% aqueous NaOH in methanol at 75 degrees C, presumably via oxidation at the benzylic position by oxygen dissolved in the solution. These easily introducible and removable nitrobenzyl groups can serve as valuable protecting groups for the synthesis of multifunctional, complex molecules. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.006

文献信息

• Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids
  作者：Marc Liniger、Yiyang Liu、Brian M. Stoltz

  DOI：10.1021/jacs.7b08496

  日期：2017.10.4

  How can you use a ruthenium isomerization catalyst twice? A ruthenium-catalyzed sequence for the formal two-carbon scission of allyl groups to carboxylic acids has been developed. The reaction includes an initial isomerization step using commercially available ruthenium catalysts followed by in situ transformation of the complex to a metal-oxo species, which is capable of catalyzing subsequent oxidation

  如何两次使用钌异构化催化剂？已经开发了一种钌催化的烯丙基正式两碳断裂成羧酸的序列。该反应包括使用市售钌催化剂的初始异构化步骤，然后将配合物原位转化为能够催化后续氧化反应的金属-氧类物质。该方法使具有挑战性的α-三取代和四取代α-氨基酸的对映选择性合成成为可能，包括抗癫痫药物左乙拉西坦的权宜之计全合成。
• Palladium(II)-Catalyzed Allylic CH Oxidation of Hindered Substrates Featuring Tunable Selectivity Over Extent of Oxidation
  作者：Xiangyou Xing、Nicholas R. O'Connor、Brian M. Stoltz

  DOI：10.1002/anie.201504007

  日期：2015.9.14

  use of Oxone and a palladium(II) catalyst enables the efficient allylic CH oxidation of sterically hindered α‐quaternary lactams which are unreactive under known conditions for similar transformations. This simple, safe, and effective system for CH activation allows for unusual tunable selectivity between a two‐electron oxidation to the allylic acetates and a four‐electron oxidation to the corresponding

  Oxone和钯（II）催化剂的使用可实现位阻α-季内酰胺的有效烯丙基CH氧化，这些胺在已知条件下无法发生类似转化。这种简单，安全，有效的CH活化系统可实现在对烯丙基乙酸酯的双电子氧化与对映体的四电子氧化之间不同寻常的可调节选择性，而主要产物取决于是否存在水。还证明了通过该方法可得到的乙酸烯丙酯和烯醛产品的通用合成效用。
• A new method for the cleavage of nitrobenzyl amides and ethers
  作者：Seo-Jung Han、Gabriel Fernando de Melo、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2014.10.006

  日期：2014.11

  A mild and efficient o- and p-nitrobenzyl cleavage protocol was developed. o- and p-nitrobenzyl groups were easily removed from a variety of substrates using 20% aqueous NaOH in methanol at 75 degrees C, presumably via oxidation at the benzylic position by oxygen dissolved in the solution. These easily introducible and removable nitrobenzyl groups can serve as valuable protecting groups for the synthesis of multifunctional, complex molecules. (C) 2014 Elsevier Ltd. All rights reserved.
• Concise synthesis of (±)-rhazinilam
  作者：Philip Magnus、Trevor Rainey

  DOI：10.1016/s0040-4020(01)00859-6

  日期：2001.10

  2-Piperidone has been converted into (+/-)-rhazinilam in nine steps in 8% overall yield. The key transformation involves the conversion of the lactam 5 into the annulated pyrrole derivative 3 via the thiophenyl imine 8. (C) 2001 Published by Elsevier Science Ltd.