tert-butyl 5-oxo-3,4-Diphenyl-5,6-dihydropyridine-1(2H)-carboxylate | 1372173-56-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: tert-butyl 5-oxo-3,4-Diphenyl-5,6-dihydropyridine-1(2H)-carboxylate
• 英文别名: Tert-butyl 5-oxo-3,4-diphenyl-5,6-dihydropyridine-1(2H)-carboxylate；tert-butyl 3-oxo-4,5-diphenyl-2,6-dihydropyridine-1-carboxylate
• CAS: 1372173-56-2
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: OFJONGZAQBTUPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-Boc-3-氮杂环丁酮 、 二苯基乙炔 在 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以79%的产率得到tert-butyl 5-oxo-3,4-Diphenyl-5,6-dihydropyridine-1(2H)-carboxylate
  参考文献：
  名称：

  通过镍催化 β-碳消除一步制备哌啶的方法

  摘要：

  描述了一种简单快捷的取代哌啶路线。Ni-膦配合物用作3-氮杂环丁酮和炔烃的[4+2]环加成反应的催化剂。该反应具有广泛的底物范围，并以优异的产率和优异的区域选择性提供哌啶。在对映体纯氮杂环丁酮的反应中，观察到立体化学的完全保留。

  DOI：

  10.1021/ol300534j

文献信息

• Regioselective Cycloaddition of 3-Azetidinones and 3-Oxetanones with Alkynes through Nickel-Catalysed Carbon-Carbon Bond Activation
  作者：Kelvin Y. T. Ho、Christophe Aïssa

  DOI：10.1002/chem.201200167

  日期：2012.3.19

  Get in the ring! The first examples of transition‐metal‐catalysed CC bond activation of 3‐azetidinones and 3‐oxetanones are reported. In the presence of a nickel catalyst and alkynes, a regioselective and high‐yielding [4+2] cycloaddition occurs, leading to the formation of pyridinones, pyranones and eventually 4,5‐disubstituted 3‐hydroxypyridines (see scheme).

  加油！过渡金属催化的C的第一实施例报道C键活化的3-氮杂环丁酮和3-氧杂环丁烷酮。在镍催化剂和炔烃的存在下，会发生区域选择性和高产率的[4 + 2]环加成反应，导致形成吡啶酮，吡喃酮，并最终形成4,5-二取代的3-羟基吡啶（参见方案）。
• A Single Step Approach to Piperidines via Ni-Catalyzed β-Carbon Elimination
  作者：Puneet Kumar、Janis Louie

  DOI：10.1021/ol300534j

  日期：2012.4.20

  An easy and expeditious route to substituted piperidines is described. A Ni-phosphine complex was used as catalyst for [4 + 2] cycloaddition of 3-azetidinone and alkynes. The reaction has broad substrate scope and affords piperidines in excellent yields and excellent regioselectivity. In the reaction of an enantiopure azetidinone, complete retention of stereochemistry was observed.

  描述了一种简单快捷的取代哌啶路线。Ni-膦配合物用作3-氮杂环丁酮和炔烃的[4+2]环加成反应的催化剂。该反应具有广泛的底物范围，并以优异的产率和优异的区域选择性提供哌啶。在对映体纯氮杂环丁酮的反应中，观察到立体化学的完全保留。
• SUBSTITUTED 3-PIPERIDONE COMPOUNDS
  申请人：Louie Janis

  公开号：US20130053565A1

  公开（公告）日：2013-02-28

  Described herein are methods for synthesizing substituted 3-piperidone compounds. Notably, substituted 3-piperidones can also be prepared in enantiopure form. The methods may allow for preparation of highly substituted piperidine cores. Also disclosed are 3-piperidone compounds and pharmaceutical compositions comprising the compounds.

  本文描述了合成取代3-哌啶酮化合物的方法。值得注意的是，取代3-哌啶酮也可以以对映纯的形式制备。这些方法可能允许制备高度取代的哌啶核。还披露了3-哌啶酮化合物和包含这些化合物的药物组合物。
• An <i>in Situ</i> Approach to Nickel-Catalyzed Cycloaddition of Alkynes and 3-Azetidinones
  作者：Ashish Thakur、Judah L. Evangelista、Puneet Kumar、Janis Louie

  DOI：10.1021/acs.joc.5b01458

  日期：2015.10.16

  An efficient and convenient procedure that generates the active Ni(0) catalyst in situ from cheap, air stable Ni(II) precursors is developed for the [4 + 2]-cycloaddition of alkynes and 3-azetidinones. The reaction affords useful 3-dehydropiperidinones in comparable yields to the reported Ni(0) procedure. Additionally, the cycloaddition with 3-oxetanone afforded the 3-dehydropyranone product. Chiral 2-substituted azetidinones were also tolerated to form substituted dehydropiperidinones in high yield and enantiomeric excess.