triisopropyl ((3-(((2S,3S)-3-vinyloxiran-2-yl)methyl)but-3-en-1-yl)oxy)silane | 1374123-45-1

• 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: triisopropyl ((3-(((2S,3S)-3-vinyloxiran-2-yl)methyl)but-3-en-1-yl)oxy)silane
• CAS: 1374123-45-1
• 化学式: C₁₈H₃₄O₂Si
• 分子量: 310.552
• InChiKey: YBXNPZKHCGFJMV-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  21.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  21.76
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三乙基硅烷 、 triisopropyl ((3-(((2S,3S)-3-vinyloxiran-2-yl)methyl)but-3-en-1-yl)oxy)silane 在 双(2,2,6,6,-四甲基-3,5-庚二酮酸)钴 、 氧气 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以62%的产率得到3,3-diethyl-10,10-diisopropyl-6,11-dimethyl-6-(((2S,3S)-3-vinyloxiran-2-yl)methyl)-4,5,9-trioxa-3,10-disiladodecane
  参考文献：
  名称：

  Exploratory studies toward the synthesis of the peroxylactone unit of plakortolides

  摘要：

  Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of beta-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the epoxide function. By this route, an advanced intermediate of plakortolides was obtained in six steps and 35% overall yield. The second approach featured a 1,2-dioxane ring forming by a double opening of bis-epoxides by ethereal hydrogen peroxide. This reaction did not proceed in the expected sense and exclusive formation of hydroperoxy tetrahydropyran derivatives was observed via a tandem oxacyclization-hydroperoxidation sequence. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.024
• 作为产物：
  描述：

  ((2S,3S)-3-(2-methylene-4-((triisopropylsilyl)oxy)butyl)oxiran-2-yl)methanol 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 triisopropyl ((3-(((2S,3S)-3-vinyloxiran-2-yl)methyl)but-3-en-1-yl)oxy)silane
  参考文献：
  名称：

  Exploratory studies toward the synthesis of the peroxylactone unit of plakortolides

  摘要：

  Our efforts in construction the 1,2-dioxane ring of plakortolides through two approaches are described. The first one involved as a key step an acid catalyzed 6-endo ring closure of beta-hydroperoxy trans-epoxides directed by a vinyl group adjacent to the epoxide function. By this route, an advanced intermediate of plakortolides was obtained in six steps and 35% overall yield. The second approach featured a 1,2-dioxane ring forming by a double opening of bis-epoxides by ethereal hydrogen peroxide. This reaction did not proceed in the expected sense and exclusive formation of hydroperoxy tetrahydropyran derivatives was observed via a tandem oxacyclization-hydroperoxidation sequence. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.024