2-Piperidino-Δ¹-pyrrolin | 1196-64-1

• 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: 2-Piperidino-Δ¹-pyrrolin
• 英文别名: 1-(3,4-dihydro-2H-pyrrol-5-yl)piperidine
• CAS: 1196-64-1
• 化学式: C₉H₁₆N₂
• 分子量: 152.239
• InChiKey: HRDTWGFMDITAQB-UHFFFAOYSA-N

物化性质

• 沸点：
  90-91 °C(Press: 2.5 Torr)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Piperidino-Δ¹-pyrrolin 在 十二羰基三钌 频哪酮 、 溶剂黄146 、 肼 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 2-(4-甲氧基苯基)哌啶
  参考文献：
  名称：

  sp³ C−H Bond Arylation Directed by Amidine Protecting Group:  α-Arylation of Pyrrolidines and Piperidines

  摘要：

  A new ruthenium-catalyzed direct sp3 C-H to C-C bond transformation is disclosed. Specifically, a method for the alpha-arylation of cyclic amines, containing either permanent (pyridine, pyrimidine) or removable (amidine) directing groups, is described. This cross-coupling reaction involves heating amine substrates with arylboronate ester at 150 degrees C in a ketone solvent with a catalytic amount of ruthenium carbonyl [Ru3(CO)12]. Arylboronate esters containing either electron-withdrawing or electron-donating substituents could be efficiently coupled. Heteroarene boronates were also effective donors.

  DOI：

  10.1021/ja064481j
• 作为产物：
  描述：

  哌啶 、 2-甲氧基-1-吡咯烷 在 溶剂黄146 作用下， 反应 1.5h， 以96%的产率得到2-Piperidino-Δ¹-pyrrolin
  参考文献：
  名称：

  sp³ C−H Bond Arylation Directed by Amidine Protecting Group:  α-Arylation of Pyrrolidines and Piperidines

  摘要：

  A new ruthenium-catalyzed direct sp3 C-H to C-C bond transformation is disclosed. Specifically, a method for the alpha-arylation of cyclic amines, containing either permanent (pyridine, pyrimidine) or removable (amidine) directing groups, is described. This cross-coupling reaction involves heating amine substrates with arylboronate ester at 150 degrees C in a ketone solvent with a catalytic amount of ruthenium carbonyl [Ru3(CO)12]. Arylboronate esters containing either electron-withdrawing or electron-donating substituents could be efficiently coupled. Heteroarene boronates were also effective donors.

  DOI：

  10.1021/ja064481j

文献信息

• C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp³CH Activation
  作者：Hana Prokopcová、Sheba D. Bergman、Karel Aelvoet、Veerle Smout、Wouter Herrebout、Benjamin Van der Veken、Lieven Meerpoel、Bert U. W. Maes

  DOI：10.1002/chem.201001887

  日期：2010.11.22

  need is an open vial! The direct α arylation of cyclic alkylamines (see scheme) requires an open vial, as the hydrogen atom involved in the C(sp3)H‐activation process is ultimately released as hydrogen gas. Reports on the formation of hydrogen gas in direct transition‐metal‐catalyzed functionalizations are still rare. Open‐vial reactions proved crucial to this direct arylation procedure as, upon sealing

  您只需要一个开放的小瓶！环状烷基胺的直接α芳基化反应（请参见方案）需要一个开放的小瓶，因为参与C（sp 3）H活化过程的氢原子最终会以氢气的形式释放出来。关于在直接过渡金属催化的官能化反应中形成氢气的报道仍然很少。小瓶反应证明对这种直接芳构化过程至关重要，因为密封后会发生催化剂失活。
• Improved Synthesis of Dialkylaminopyrrolines
  作者：David A. Flosser、Roy A. Olofson

  DOI：10.1081/scc-120021030

  日期：2003.7

  The literature synthesis of 5-dialkylamino-3,4-dihydro-2H-pyrroles from 5-methoxy-3,4-dihydro-2H-pyrrole has been much improved. In initial assays, the pyrrolinium salts obtained on alkylation of the dibutylamino ami dine are excellent "naked halide" catalysts.
• sp³ C−H Bond Arylation Directed by Amidine Protecting Group:  α-Arylation of Pyrrolidines and Piperidines
  作者：Stefan J. Pastine、Denis V. Gribkov、Dalibor Sames

  DOI：10.1021/ja064481j

  日期：2006.11.1

  A new ruthenium-catalyzed direct sp3 C-H to C-C bond transformation is disclosed. Specifically, a method for the alpha-arylation of cyclic amines, containing either permanent (pyridine, pyrimidine) or removable (amidine) directing groups, is described. This cross-coupling reaction involves heating amine substrates with arylboronate ester at 150 degrees C in a ketone solvent with a catalytic amount of ruthenium carbonyl [Ru3(CO)12]. Arylboronate esters containing either electron-withdrawing or electron-donating substituents could be efficiently coupled. Heteroarene boronates were also effective donors.