(-)-4-(4-nitrophenyl)-hexan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-4-(4-nitrophenyl)-hexan-2-one
• 英文别名: 4-(p-nitro-phenyl)-hexan-2-one；(4R)-4-(4-nitrophenyl)hexan-2-one
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: AKGFMGPTPJIQGE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(p-nitrophenyl)-3-butene-2-one 、 diethylzinc 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 1,4-bis(2-((S)-4-phenyl-4,5-dihydrooxazol-2-yl)propan-2-yl)phthalazine 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (-)-4-(4-nitrophenyl)-hexan-2-one 、 (+)-4-(4-nitrophenyl)-hexan-2-one
  参考文献：
  名称：

  Chiral dinuclear phthalazine bridged bisoxazoline ligands: synthesis and application in enantioselective Cu-catalyzed conjugate addition of ZnEt2 to enones

  摘要：

  A new class of chiral dinuclear ligands with phthalazine bridged bisoxazoline scaffold was designed and prepared in convenient synthetic routes. H-1 NMR analysis showed that this class of ligands could coordinate with two metal ions, either same or different. These ligands afforded good to excellent yields and enantioselectivities in Cu-catalyzed conjugate addition of ZnEt2 to enones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.098

文献信息

• Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Acyclic Aliphatic Enones
  作者：Hirotake Mizutani、Sylvia J. Degrado、Amir H. Hoveyda

  DOI：10.1021/ja0122849

  日期：2002.2.1

  Cu-catalyzed enantioselective conjugate additions to acyclic aliphatic enones are reported. The resulting enolates may be functionalized intra- and intermolecularly, leading to the formation of an additional C-C bond. The utility of the present method is not limited to reactions involving Et2Zn; a variety of alkylzincs may be used. Moreover, many of the requisite substrates can be easily accessed through

  报道了铜催化的对映选择性共轭添加到无环脂肪族烯酮。所得的烯醇可以在分子内和分子间进行功能化，从而形成额外的 CC 键。本方法的用途不限于涉及 Et2Zn 的反应；可以使用多种烷基锌。此外，许多必需的底物可以通过催化烯烃交叉复分解轻松获得。
• Chiral dinuclear phthalazine bridged bisoxazoline ligands: synthesis and application in enantioselective Cu-catalyzed conjugate addition of ZnEt2 to enones
  作者：Liang Zhang、Guoqiang Yang、Chaoren Shen、Sabah Arghib、Wanbin Zhang

  DOI：10.1016/j.tetlet.2011.02.098

  日期：2011.5

  A new class of chiral dinuclear ligands with phthalazine bridged bisoxazoline scaffold was designed and prepared in convenient synthetic routes. H-1 NMR analysis showed that this class of ligands could coordinate with two metal ions, either same or different. These ligands afforded good to excellent yields and enantioselectivities in Cu-catalyzed conjugate addition of ZnEt2 to enones. (C) 2011 Elsevier Ltd. All rights reserved.