1-benzyl-3,5-dicyclohex-1-enyl-1H-pyridin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-benzyl-3,5-dicyclohex-1-enyl-1H-pyridin-2-one
• 英文别名: 1-benzyl-4,6-dicyclohexenyl-2-pyridone；1-Benzyl-4,6-di(cyclohexen-1-yl)pyridin-2-one；1-benzyl-4,6-di(cyclohexen-1-yl)pyridin-2-one
• 化学式: C₂₄H₂₇NO
• 分子量: 345.484
• InChiKey: BXVJDVSLRNEZTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-乙炔基环己烷 、 异氰酸苄酯 在 chlorobis(ethylene)rhodium(I) dimer 、 4,8-bis(1,1-tert-butyl)-Ν,Ν,1,2,10,11-hexamethyldibenzo[df][1,3,2]-2-dioxaphospho-6-amine 作用下， 以 甲苯 为溶剂， 以92%的产率得到1-benzyl-3,5-dicyclohex-1-enyl-1H-pyridin-2-one
  参考文献：
  名称：

  Regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of alkynes and isocyanates to form pyridones

  摘要：

  A highly regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of terminal alkynes with a variety of isocyanates to provide 2- and 4-pyridones has been developed. This reaction proceeds in good to excellent yields and overcomes the problem of dimerization and trimerization through the use of phosphoramidite ligands. A CO migration in the metallacycle is proposed to account for the formation of 4-pyridone. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.021

文献信息

• Rhodium-Catalyzed Chemo-, Regio-, and Enantioselective [2 + 2 + 2] Cycloaddition of Alkynes with Isocyanates
  作者：Ken Tanaka、Azusa Wada、Keiichi Noguchi

  DOI：10.1021/ol052041b

  日期：2005.10.1

  chemoselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates leading to a wide range of 2-pyridones. This method was successfully applied to the chemo-, regio-, and enantioselective synthesis of axially chiral 2-pyridones from unsymmetrical alpha,omega-diynes, bearing an ortho-substituted phenyl at one terminal position, and alkyl isocyanates.

  [反应：见正文]我们已经开发出阳离子铑（I）/修饰的BINAP络合物催化的炔烃与异氰酸酯的化学选择性[2 + 2 + 2]环加成反应，从而制得各种2-吡啶酮。该方法已成功地用于由不对称的α，ω-二炔，在一个末端带有邻位取代的苯基和异氰酸烷基酯的轴向手性2-吡啶酮的化学，区域和对映选择性合成。
• Regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of alkynes and isocyanates to form pyridones
  作者：Kevin M. Oberg、Ernest E. Lee、Tomislav Rovis

  DOI：10.1016/j.tet.2009.02.021

  日期：2009.6

  A highly regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of terminal alkynes with a variety of isocyanates to provide 2- and 4-pyridones has been developed. This reaction proceeds in good to excellent yields and overcomes the problem of dimerization and trimerization through the use of phosphoramidite ligands. A CO migration in the metallacycle is proposed to account for the formation of 4-pyridone. (C) 2009 Elsevier Ltd. All rights reserved.