8-(bromomethylsulfonyl)-3-methylidene-8-azabicyclo[3.2.1]octane | 303184-39-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 8-(bromomethylsulfonyl)-3-methylidene-8-azabicyclo[3.2.1]octane
• CAS: 303184-39-6
• 化学式: C₉H₁₄BrNO₂S
• 分子量: 280.186
• InChiKey: UJESDWWSBNDMKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-(bromomethylsulfonyl)-3-methylidene-8-azabicyclo[3.2.1]octane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 5.0h， 以55%的产率得到3-methylidene-8-methylsulfonyl-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Radical and Anionic Response of N-(Bromomethanesulfonyl)-Substituted α,α‘-Bridged Piperidine Substrates

  摘要：

  The N-(bromomethanesulfonyl) azabicyclic ketones 2a-c and their exo-methylene analogues 1a-c were prepared. Our examination of the radical-induced behavior of the latter triad provided experimental evidence for the propensity of the b and c systems to engage in 7-endo cyclization. For 1a, only reductive debromination was observed. In no instance was ring closure by the B-exo radical mode seen. As concerns ketones 2a-c, all three showed a remarkable facility for engaging in intramolecular S(N)2 displacement in the presence of KHMDS. Yields at the mid-80% level were realized irrespective of the value of it. Molecular mechanics calculations of the Monte Carlo type were performed on several conformational isomers and product classes in an effort to provide support for the explanatory conclusions offered as rationale-for the collective experimental observations.

  DOI：

  10.1021/jo000873b
• 作为产物：
  描述：

  去甲托品酮盐酸盐 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.75h， 生成 8-(bromomethylsulfonyl)-3-methylidene-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Radical and Anionic Response of N-(Bromomethanesulfonyl)-Substituted α,α‘-Bridged Piperidine Substrates

  摘要：

  The N-(bromomethanesulfonyl) azabicyclic ketones 2a-c and their exo-methylene analogues 1a-c were prepared. Our examination of the radical-induced behavior of the latter triad provided experimental evidence for the propensity of the b and c systems to engage in 7-endo cyclization. For 1a, only reductive debromination was observed. In no instance was ring closure by the B-exo radical mode seen. As concerns ketones 2a-c, all three showed a remarkable facility for engaging in intramolecular S(N)2 displacement in the presence of KHMDS. Yields at the mid-80% level were realized irrespective of the value of it. Molecular mechanics calculations of the Monte Carlo type were performed on several conformational isomers and product classes in an effort to provide support for the explanatory conclusions offered as rationale-for the collective experimental observations.

  DOI：

  10.1021/jo000873b