2-oxo-N-propylcyclopentanecarboxamide | 31917-27-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxo-N-propylcyclopentanecarboxamide
• 英文别名: 2-oxo-cyclopentanecarboxylic acid propylamide；2-Oxo-cyclopentancarbonsaeure-propylamid；2-oxo-N-propylcyclopentane-1-carboxamide
• CAS: 31917-27-8
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: HMTTUBNVQCGJRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-甲氧基儿茶酚 、 2-oxo-N-propylcyclopentanecarboxamide 在 polymer-supported 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine 、 polymer-supported periodate 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine

  摘要：

  Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (+/-)-powelline and (+/-)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.132

文献信息

• An Organocatalytic Oxidative Coupling Strategy for the Direct Synthesis of Arylated Quaternary Stereogenic Centers
  作者：Katherine M. Bogle、David J. Hirst、Darren J. Dixon

  DOI：10.1021/ol702277v

  日期：2007.11.1

  A broadly applicable oxidative coupling strategy of 3-substituted catechols and carbon-centered pro-nucleophiles for the construction of arylated quaternary stereogenic centers has been developed. Pivoting on a base-catalyzed addition of a carbon-centered acid to an in situ generated o-benzoquinone, the method is general and atom-economical and provides remarkably efficient access to one of the most challenging structural motifs. Furthermore, use of chiral bifunctional organocatalysts allows the process to be rendered asymmetric (up to 81% ee).
• US4985305A
  申请人：——

  公开号：US4985305A

  公开（公告）日：1991-01-15
• An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine
  作者：Katherine M. Bogle、David J. Hirst、Darren J. Dixon

  DOI：10.1016/j.tet.2010.04.132

  日期：2010.8

  Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (+/-)-powelline and (+/-)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. (C) 2010 Elsevier Ltd. All rights reserved.