(2S)-1-triisopropylsiloxy-2-((3S,6R)-6-methoxy-6-((4E,6E)-nona-4,6-dienyl)-1,2-dioxan-3-yl)propane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2S)-1-triisopropylsiloxy-2-((3S,6R)-6-methoxy-6-((4E,6E)-nona-4,6-dienyl)-1,2-dioxan-3-yl)propane
• 英文别名: [(2S)-2-[(3S,6R)-6-methoxy-6-[(4E,6E)-nona-4,6-dienyl]dioxan-3-yl]propoxy]-tri(propan-2-yl)silane
• 化学式: C₂₆H₅₀O₄Si
• 分子量: 454.766
• InChiKey: NVUMIDLDVQAKQK-NYLNDKJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.96
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-1-triisopropylsiloxy-2-((3S,6R)-6-methoxy-6-((4E,6E)-nona-4,6-dienyl)-1,2-dioxan-3-yl)propane 在 四丁基氟化铵 作用下， 生成 (2S)-2-((3S,6R)-6-methoxy-6-((4E,6E)-nona-4,6-dienyl)-1,2-dioxan-3-yl)propan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of 1,2-dioxanes: approaches to the peroxyplakoric acids

  摘要：

  The stereospecific intramolecular alkylation of a hydroperoxyacetal provides the basis for the first asymmetric synthesis of the dioxane propionate core of the peroxyplakorates. Chemoselective hydrometallation of an alkyne in the presence of a peroxide is used to introduce a synthon for the polyunsaturated side chains of the peroxyplakorates. The route suggests a general solution for the 1,2-dioxane unit in many peroxide natural products. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.068
• 作为产物：
  描述：

  1-丁炔 、 (2S)-1-triisopropylsiloxy-2-((3S,6R)-6-methoxy-6-((5E)-5-iodopent-4-enyl)-1,2-dioxan-3-yl)propane 在 Schwartz's reagent 、 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.75h， 以18%的产率得到(2S)-1-triisopropylsiloxy-2-((3S,6R)-6-methoxy-6-((4E,6E)-nona-4,6-dienyl)-1,2-dioxan-3-yl)propane
  参考文献：
  名称：

  Asymmetric synthesis of 1,2-dioxanes: approaches to the peroxyplakoric acids

  摘要：

  The stereospecific intramolecular alkylation of a hydroperoxyacetal provides the basis for the first asymmetric synthesis of the dioxane propionate core of the peroxyplakorates. Chemoselective hydrometallation of an alkyne in the presence of a peroxide is used to introduce a synthon for the polyunsaturated side chains of the peroxyplakorates. The route suggests a general solution for the 1,2-dioxane unit in many peroxide natural products. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.068

文献信息

• Asymmetric synthesis of 1,2-dioxanes: approaches to the peroxyplakoric acids
  作者：Chunping Xu、Chris Schwartz、Joseph Raible、Patrick H. Dussault

  DOI：10.1016/j.tet.2009.09.068

  日期：2009.11

  The stereospecific intramolecular alkylation of a hydroperoxyacetal provides the basis for the first asymmetric synthesis of the dioxane propionate core of the peroxyplakorates. Chemoselective hydrometallation of an alkyne in the presence of a peroxide is used to introduce a synthon for the polyunsaturated side chains of the peroxyplakorates. The route suggests a general solution for the 1,2-dioxane unit in many peroxide natural products. (C) 2009 Elsevier Ltd. All rights reserved.