(5-Methoxymethoxy-4,4-dimethyl-octa-6,7-dien-1-ynyl)-trimethyl-silane | 214463-74-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5-Methoxymethoxy-4,4-dimethyl-octa-6,7-dien-1-ynyl)-trimethyl-silane
• CAS: 214463-74-8
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: LUIHVNGXHWIAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-Methoxymethoxy-4,4-dimethyl-octa-6,7-dien-1-ynyl)-trimethyl-silane 、 alkaline earth salt of/the/ methylsulfuric acid 在 二甲基亚砜 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (6S,6aS)-6-Methoxymethoxy-5,5-dimethyl-1-methylene-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one 、 (6R,6aS)-6-Methoxymethoxy-5,5-dimethyl-1-methylene-3-trimethylsilanyl-4,5,6,6a-tetrahydro-1H-pentalen-2-one
  参考文献：
  名称：

  An Intramolecular Allenic [2 + 2 + 1] Cycloaddition

  摘要：

  A new stereo- and regioselective method for the preparation of alpha-methylene and 4-alkylidene cyclopentenones is described. These substructures were achieved by an intramolecular [2 + 2 + 1] cycloaddition of an allene, alkyne, and carbon monoxide moieties to afford the target compounds stereoselectively and in good yields. In some cases, the target compounds were obtained as mixtures, but it is demonstrated that the formation of either the alpha-methylene or 4-alkylidene cyclopentenone can be controlled by the allene structure or reaction conditions. Monosubstituted allenes afford alpha-methylene cyclopentenones as the only cycloadduct. Disubstitution on the allene alters the course of the allenic [2 + 2 + 1] reaction. 3,3-Disubstituted allenes undergo cycloaddition with the least substituted pi-bond of the allene. This affords the bicyclo[4.3.0]nonane ring system. Cycloaddition of 1,3-disubstituted allenes afford mixtures of several possible cycloadducts. However, it has been shown that good control over the product ratio can be obtained by altering the cycloaddition conditions and that the regiochemistry can be directed depending upon the metal used.

  DOI：

  10.1021/jo980548c
• 作为产物：
  描述：

  5,5-Dimethyl-8-trimethylsilanyl-octa-2,7-diyn-4-ol 在 copper(l) iodide 、 聚合甲醛 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (5-Methoxymethoxy-4,4-dimethyl-octa-6,7-dien-1-ynyl)-trimethyl-silane
  参考文献：
  名称：

  An Intramolecular Allenic [2 + 2 + 1] Cycloaddition

  摘要：

  A new stereo- and regioselective method for the preparation of alpha-methylene and 4-alkylidene cyclopentenones is described. These substructures were achieved by an intramolecular [2 + 2 + 1] cycloaddition of an allene, alkyne, and carbon monoxide moieties to afford the target compounds stereoselectively and in good yields. In some cases, the target compounds were obtained as mixtures, but it is demonstrated that the formation of either the alpha-methylene or 4-alkylidene cyclopentenone can be controlled by the allene structure or reaction conditions. Monosubstituted allenes afford alpha-methylene cyclopentenones as the only cycloadduct. Disubstitution on the allene alters the course of the allenic [2 + 2 + 1] reaction. 3,3-Disubstituted allenes undergo cycloaddition with the least substituted pi-bond of the allene. This affords the bicyclo[4.3.0]nonane ring system. Cycloaddition of 1,3-disubstituted allenes afford mixtures of several possible cycloadducts. However, it has been shown that good control over the product ratio can be obtained by altering the cycloaddition conditions and that the regiochemistry can be directed depending upon the metal used.

  DOI：

  10.1021/jo980548c