1-butyl-3,5,5-trimethylcyclohex-2-en-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-butyl-3,5,5-trimethylcyclohex-2-en-1-ol
• 化学式: C₁₃H₂₄O
• 分子量: 196.333
• InChiKey: LKKQJYXYCDPRPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 异佛尔酮 在 copper(l) iodide 、 lithium 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以52%的产率得到1-butyl-3,5,5-trimethylcyclohex-2-en-1-ol
  参考文献：
  名称：

  The Copper Mediated Barbier Reactions of α,β-Unsaturated Ketones: Regioselective Conjugate and 1,2-Addition

  摘要：

  The one-pot reaction of isophorone and other alpha,beta-unsaturated ketones with alkyl and aryl halides in the presence of magnesium and a copper salt ("Barbier" conditions) leads to the regiospecific formation of 1,4-addition products; the use of lithium leads to regioselective 1,2-addition.

  DOI：

  10.1080/00397919908085932

文献信息

• Some Observations on the Mechanism of Diorganocuprate 1,4-Addition Reactions with α,β-Unsaturated Ketones:  Effects of Diethyl Ether in Reactions of Butylcoppers in Toluene
  作者：Celia L. Kingsbury、Robin A. J. Smith

  DOI：10.1021/jo970316y

  日期：1997.7.1

  Mixtures of butyllithium and copper iodide prepared in toluene react with alpha,beta-unsaturated ketones predominantly in a 1,2-fashion. Addition of 2 equiv of diethyl ether to the system results in a dramatic preference for the 1,4-product, as found normally with diorganocuprates in ethereal solvents. These results are in accordance with the theoretical predictions that a suitable ligand is required to facilitate the stabilization of a formally copper(III) reaction intermediate on the 1,4-addition mechanistic pathway.
• The Copper Mediated Barbier Reactions of α,β-Unsaturated Ketones: Regioselective Conjugate and 1,2-Addition
  作者：Declan P. Costello、Niall W. A. Geraghty

  DOI：10.1080/00397919908085932

  日期：1999.9

  The one-pot reaction of isophorone and other alpha,beta-unsaturated ketones with alkyl and aryl halides in the presence of magnesium and a copper salt ("Barbier" conditions) leads to the regiospecific formation of 1,4-addition products; the use of lithium leads to regioselective 1,2-addition.