(E)-2,5-dimethyl-1,3-nonadiene | 132592-72-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (E)-2,5-dimethyl-1,3-nonadiene
• 英文别名: (3E)-2,5-dimethylnona-1,3-diene
• CAS: 132592-72-4
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: OMSORCARHLCDTO-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (E)-2-methyl-1,4-hexadien-3-ol 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 生成 (E)-2,5-dimethyl-1,3-nonadiene
  参考文献：
  名称：

  Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents

  摘要：

  Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph gives only the fully conjugated gamma-coupling product. With LiCuBu2, substantial loss of double-bond configuration occurs to give primarily the all-trans coupling product. With other cuprates, no detectable loss of double-bond configuration was observed. Cross coupling (Z)-3-(2-phenylethenyl)2-cyclohexen-1-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN) ph gives only alpha-coupling product; with LiCu(CN)Bu, a mixture of alpha, gamma, and epsilon coupling product was obtained. Cross coupling with LiCuBu2, results in loss of double-bond configuration in the alpha-alkylation product. With the other cuprates, no loss of double-bond configuration was detected in the alpha and gamma coupling product. These results have profound mechanistic implications, which are discussed. The relationship between structure and reactivity was also investigated. A variety of diallylic pivalates (1-5 OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph. Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.

  DOI：

  10.1021/jo00007a055

文献信息

• UNDERINER, TED L.;GOERING, HARLAN L., J. ORG. CHEM., 56,(1991) N, C. 2563-2572
  作者：UNDERINER, TED L.、GOERING, HARLAN L.

  DOI：——

  日期：——
• Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents
  作者：Ted L. Underiner、Harlan L. Goering

  DOI：10.1021/jo00007a055

  日期：1991.3

  Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph gives only the fully conjugated gamma-coupling product. With LiCuBu2, substantial loss of double-bond configuration occurs to give primarily the all-trans coupling product. With other cuprates, no detectable loss of double-bond configuration was observed. Cross coupling (Z)-3-(2-phenylethenyl)2-cyclohexen-1-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN) ph gives only alpha-coupling product; with LiCu(CN)Bu, a mixture of alpha, gamma, and epsilon coupling product was obtained. Cross coupling with LiCuBu2, results in loss of double-bond configuration in the alpha-alkylation product. With the other cuprates, no loss of double-bond configuration was detected in the alpha and gamma coupling product. These results have profound mechanistic implications, which are discussed. The relationship between structure and reactivity was also investigated. A variety of diallylic pivalates (1-5 OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph. Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.