6-(benzyloxy)-1,1-dideuterio-3-ethyl-1,2-hexadiene

• 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: 6-(benzyloxy)-1,1-dideuterio-3-ethyl-1,2-hexadiene
• 化学式: C₁₅H₂₀O
• 分子量: 218.307
• InChiKey: FDSHJSJWRVXEBY-DICFDUPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-benzyloxy-1-pentyne 在 4-二甲氨基吡啶 、 copper(l) iodide 、 正丁基锂 、 三氯化铝 、 lithium aluminium deuteride 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 6-(benzyloxy)-1,1-dideuterio-3-ethyl-1,2-hexadiene
  参考文献：
  名称：

  Stereogenic Propargylic Centers via Base-Mediated Terminal Allene Isomerization

  摘要：

  A study of alkali metal amide-mediated isomerizations of terminal allenes is described. The isomerizations of substituted ethenylidenecyclohexanes to form diastereomeric mixtures of terminal alkynes have been conducted to determine factors which may influence the stereochemistry at the newly formed propargylic centers. An initial base screen revealed that potassium N-methylbutylamide (KMBA) exhibits the highest level of equatorial to axial alkyne diastereoselectivity. With the severely hindered terminal allene 26, the use of potassium 3-aminopropylamide is required to effect isomerization. A general synthesis of deuterated terminal allenes has also been achieved, and a mechanistic study using d(2)-allenes 18a,b has revealed the involvement of a propargylic anion in the course of the KMBA-mediated isomerizations.

  DOI：

  10.1021/jo960276i

文献信息

• Stereogenic Propargylic Centers <i>via</i> Base-Mediated Terminal Allene Isomerization
  作者：John D. Spence、Justin K. Wyatt、Daniel M. Bender、David K. Moss、Michael H. Nantz

  DOI：10.1021/jo960276i

  日期：1996.1.1

  A study of alkali metal amide-mediated isomerizations of terminal allenes is described. The isomerizations of substituted ethenylidenecyclohexanes to form diastereomeric mixtures of terminal alkynes have been conducted to determine factors which may influence the stereochemistry at the newly formed propargylic centers. An initial base screen revealed that potassium N-methylbutylamide (KMBA) exhibits the highest level of equatorial to axial alkyne diastereoselectivity. With the severely hindered terminal allene 26, the use of potassium 3-aminopropylamide is required to effect isomerization. A general synthesis of deuterated terminal allenes has also been achieved, and a mechanistic study using d(2)-allenes 18a,b has revealed the involvement of a propargylic anion in the course of the KMBA-mediated isomerizations.