8-Trimethylsilyloct-6-ynal | 225376-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-Trimethylsilyloct-6-ynal
• CAS: 225376-10-3
• 化学式: C₁₁H₂₀OSi
• 分子量: 196.365
• InChiKey: FHRPBFJWZMDUJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-Trimethylsilyloct-6-ynal 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以66%的产率得到2-ethenylidene-1-cyclohexanol
  参考文献：
  名称：

  Formal Synthesis of d-myo-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol

  摘要：

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).

  DOI：

  10.1021/jo990086i
• 作为产物：
  描述：

  2H-吡喃,2-(6-庚炔-1-氧基)四氢 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 21.0h， 生成 8-Trimethylsilyloct-6-ynal
  参考文献：
  名称：

  Formal Synthesis of d-myo-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol

  摘要：

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).

  DOI：

  10.1021/jo990086i

文献信息

• Formal Synthesis of <scp>d</scp>-<i>myo</i>-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol
  作者：Derrick L. J. Clive、Xiao He、Maarten H. D. Postema、M. Jeffrey Mashimbye

  DOI：10.1021/jo990086i

  日期：1999.6.1

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).