(E)-ethyl 5-methylene-7-((triisopropylsilyl)oxy)hept-2-enoate | 1374123-41-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 5-methylene-7-((triisopropylsilyl)oxy)hept-2-enoate
• CAS: 1374123-41-7
• 化学式: C₁₉H₃₆O₃Si
• 分子量: 340.579
• InChiKey: DMCWYIRSHUMZOJ-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  23.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 5-methylene-7-((triisopropylsilyl)oxy)hept-2-enoate 在 二异丁基氢化铝 、 rochelle salt 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以85%的产率得到(E)-5-methylene-7-((triisopropylsilyl)oxy)hept-2-en-1-ol
  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：

  triisopropyl((3-methylbut-3-en-1-yl)oxy)silane 、 丙炔酸乙酯 在 二氯乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以77%的产率得到(E)-ethyl 5-methylene-7-((triisopropylsilyl)oxy)hept-2-enoate
  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