[(CH3)2Cu(2-cyclohexenone)Li] | 267219-61-4

• 英文名称: [(CH3)2Cu(2-cyclohexenone)Li]
• CAS: 267219-61-4
• 化学式: C₈H₁₄CuLiO
• 分子量: 196.686
• InChiKey: WBFLFJKICFFDCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
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• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  [(CH3)Cu(thienyl)Li] 、 [(CH3)Cu(thienyl)(2-cyclohexenone)Li] 以 氘代四氢呋喃 为溶剂， 生成 [(CH3)2Cu(2-cyclohexenone)Li]
  参考文献：
  名称：

  通过自组织使有机化合物的复杂性最小化：混合铜酸盐π络合物的显着取向效应

  摘要：

  他们“知道”去哪里：一个强大的取向效应在混合有机铜[R的复合物中观察到Ť ř NT CuLi]和底物使用C  C，C  N，和C  š双键（参见方案; TH =噻吩基）。中间配合物的优选几何形状建立了将R T容易地添加到双键中，而不是添加了“虚拟配体” R NT。

  DOI：

  10.1002/anie.201107060

文献信息

• Complexes of the Gilman Reagent with Double Bonds across the π–σ Continuum
  作者：Steven H. Bertz、Stephen K. Cope、Richard A. Hardin、Michael D. Murphy、Craig A. Ogle、David T. Smith、Andy A. Thomas、Tara N. Whaley

  DOI：10.1021/om300622c

  日期：2012.11.26

  By using rapid injection NMR at low temperatures, a variety of pi-complexes of lithium dimethylcuprate(I) with C-C, C-N, and C-S double bonds have been prepared and characterized. Complexation is generally accompanied by large upfield changes in chemical shift for the substrate carbon atoms bonded to copper. In the case of alpha,beta-unsaturated carbonyl compounds, the changes for the carbonyl carbons are much smaller in magnitude, which is consistent with the usual eta(2) representation of these structures. It is possible for one ligand to displace another, and in this way an order of stability can be elucidated. Treatment of selected pi-complexes with chlorosilanes or cyanosilanes gives Cu-III intermediates.
• Rapid-Injection NMR Study of Iodo- and Cyano-Gilman Reagents with 2-Cyclohexenone:  Observation of π-Complexes and Their Rates of Formation
  作者：Steven H. Bertz、Clifford M. Carlin、Daniel A. Deadwyler、Michael D. Murphy、Craig A. Ogle、Paul H. Seagle

  DOI：10.1021/ja027744s

  日期：2002.11.1

  Rapid-injection is a very useful technique for the preparation of temperature-sensitive and air-sensitive compounds in the cold, nitrogen-filled probe of an NMR spectrometer. We have used this method to prepare solutions of pi-complexes from 2-cyclohexenone and prototypical cuprates Me2CuLi.LiI and Me2CuLi.LiCN, and we have assigned structures on the basis of 1H and 13C NMR. In each case two pi-complexes were observed, and in the former, their rates of formation were measured by rapid-injection 1H NMR and EXSY spectroscopy. These results provide insights into the normal and anomalous conjugate addition reactions of organocuprates.