γ-tert-butyl-δ-valerolactone | 105592-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: γ-tert-butyl-δ-valerolactone
• 英文别名: 4-tert-Butyl-δ-valerolactone；4-tert-butyloxan-2-one
• CAS: 105592-09-4
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: YZRDCZCCRKJBPM-UHFFFAOYSA-N

物化性质

• 沸点：
  222.9±8.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,6-dihydro-pyran-2-one 、 叔丁基锂 生成 γ-tert-butyl-δ-valerolactone
  参考文献：
  名称：

  Iodotrimethylsilane-promoted additions of monoorganocopper compounds to .alpha.,.beta.-unsaturated ketones, esters, and lactones

  摘要：

  Conjugate additions with the efficient monoorganocopper-iodotrimethylsilane combination, exemplified plified mainly with methylcopper, butylcopper, and tert-butylcopper, proceed cleanly, smoothly, and rapidly to a variety of alpha,beta-unsaturated carbonyl compounds; cyclic and acyclic enones, beta-alkoxy enones, enoates and lactones in ether, THF, and dichloromethane, often at -78-degrees-C. The RCu-(LiI)-TMSI reagent gives a good economy of group transfer with good to excellent yields of conjugate adducts. Lithium iodide, present from preparation of the organocopper compounds, increases the rate of the reactions and is a favorable component. Additions are faster, but somewhat less selective, in THF than in ether. Careful workup after addition of triethylamine or pyridine at low temperature permits isolation of TMS enol ethers and TMS ketene acetals. Acyclic enones preferentially give the Z-silyl enol ethers. The RCu(LiI)-TMSI system is a most useful alternative to the conventional lithium diorganocuprates in conjugate additions.

  DOI：

  10.1021/jo00077a055

文献信息

• Russell, Glen A.; Shi, Bing Zhi; Jiang, Wan, Journal of the American Chemical Society, 1995, vol. 117, # 14, p. 3952 - 3962
  作者：Russell, Glen A.、Shi, Bing Zhi、Jiang, Wan、Hu, Shuiesheng、Kim, Byeong H.、Baik, Woonphil

  DOI：——

  日期：——
• Russell, Glen A.; Baik, Woonphil; Ngoviwatchai, Preecha, Acta Chemica Scandinavica, 1990, vol. 44, # 2, p. 170 - 177
  作者：Russell, Glen A.、Baik, Woonphil、Ngoviwatchai, Preecha、Kim, Byeong Hyo

  DOI：——

  日期：——
• Russell, Glen A.; Guo, Deliang; Baik, Woonphil, Heterocycles, 1989, vol. 28, # 1, p. 143 - 146
  作者：Russell, Glen A.、Guo, Deliang、Baik, Woonphil、Herron

  DOI：——

  日期：——
• SEYFERTH, D.;HUI, R. C., TETRAHEDRON LETT., 1986, 27, N 13, 1473-1476
  作者：SEYFERTH, D.、HUI, R. C.

  DOI：——

  日期：——