6-Nitro-1-trimethylsilanyl-decane-2,9-dione

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-Nitro-1-trimethylsilanyl-decane-2,9-dione
• 英文别名: 6-Nitro-1-trimethylsilyldecane-2,9-dione
• 化学式: C₁₃H₂₅NO₄Si
• 分子量: 287.431
• InChiKey: BKKKGADNRCUQFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (三甲基硅基)甲基氯化镁 、 2-nitro-2-(3'-oxobutyl)cyclopentanone 以 四氢呋喃 为溶剂， 以73%的产率得到6-Nitro-1-trimethylsilanyl-decane-2,9-dione
  参考文献：
  名称：

  Retro Claisen cleavage of α-nitrocycloalkanones using trimethylsilylmethylmagnesium chloride (Peterson reagent): Synthesis of functionalized β-keto-trimethylsilanes.

  摘要：

  Beta-ketosilanes, bearing a nitro functionality, can be prepared by nucleophilic ring cleavage of alpha-nitrocycloalkanones with the Peterson reagent. This high yielding process shows considerable chemoselectivity but fails with large rings (C(n)>7). This unusual reactivity is tentatively explained considering the silicon beta effect.

  DOI：

  10.1016/s0040-4039(00)73688-4

文献信息

• Retro Claisen cleavage of α-nitrocycloalkanones using trimethylsilylmethylmagnesium chloride (Peterson reagent): Synthesis of functionalized β-keto-trimethylsilanes.
  作者：Roberto Ballini、Giuseppe Bartoli、Riccardo Giovannini、Enrico Marcantoni、Marino Petrini

  DOI：10.1016/s0040-4039(00)73688-4

  日期：1993.5

  Beta-ketosilanes, bearing a nitro functionality, can be prepared by nucleophilic ring cleavage of alpha-nitrocycloalkanones with the Peterson reagent. This high yielding process shows considerable chemoselectivity but fails with large rings (C(n)>7). This unusual reactivity is tentatively explained considering the silicon beta effect.