(2R,3S)-3-(2-methylene-4-((triisopropylsilyl)oxy)butyl)oxirane-2-carbaldehyde | 1374123-56-4

• 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: (2R,3S)-3-(2-methylene-4-((triisopropylsilyl)oxy)butyl)oxirane-2-carbaldehyde
• CAS: 1374123-56-4
• 化学式: C₁₇H₃₂O₃Si
• 分子量: 312.525
• InChiKey: WYJSIXLTKLQAPI-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 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：
  0.82
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(2-methylene-4-((triisopropylsilyl)oxy)butyl)oxirane-2-carbaldehyde 在 双(2,2,6,6,-四甲基-3,5-庚二酮酸)钴 、 氧气 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 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：

  (E)-ethyl 5-methylene-7-((triisopropylsilyl)oxy)hept-2-enoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 2,2,6,6-四甲基哌啶氧化物 、 L-(+)-酒石酸二乙酯 、 碘苯二乙酸 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 为溶剂， 反应 56.5h， 生成 (2R,3S)-3-(2-methylene-4-((triisopropylsilyl)oxy)butyl)oxirane-2-carbaldehyde
  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