8-benzyl-2,2-ethylenedioxy-8-azabicyclo<3.2.1>oct-3-en-6-one | 153172-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-benzyl-2,2-ethylenedioxy-8-azabicyclo<3.2.1>oct-3-en-6-one
• CAS: 153172-86-2
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: UFZCDCKRZBVKDD-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  8-benzyl-2,2-ethylenedioxy-8-azabicyclo<3.2.1>oct-3-en-6-one 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 78.0h， 生成 8-benzyl-6α-acetoxy-8-azabicyclo<3.2.1>octan-2-one
  参考文献：
  名称：

  Synthesis of (±)-2b-Hydroxy-6a-acetoxynortropane

  摘要：

  8-Benzyl-6alpha-chloro-6beta-carbonitrile-2,2-ethylgnedioxy-8-azabicyclo[3.2.1]oct-3-ene (8) and its C(6) epimer (9) were hydrolyzed to afford 6-ketone (10). Reduction of the ketone (10) with sodium borohydride gave predominantly 6alpha-ol (14). 2-Ketone (20), obtained from 14 by deprotection followed by hydrogenation and acetylation, was reduced with sodium borohydride to give 2beta-ol a as the major epimer. Nortropane (24) was prepared from 21 by debenzylation.

  DOI：

  10.3987/com-93-6480
• 作为产物：
  描述：

  8-benzyl-6β-chloro-6α-carbonitrile-2,2-ethylenedioxy-8-azabicyclo<3.2.1>oct-3-ene 在 氢氧化钾 作用下， 以 水 、 叔丁醇 为溶剂， 反应 8.0h， 以41.3%的产率得到8-benzyl-2,2-ethylenedioxy-6β-chloro-8-azabicyclo<3.2.1>oct-3-en-6α-amide
  参考文献：
  名称：

  Synthesis of (±)-2b-Hydroxy-6a-acetoxynortropane

  摘要：

  8-Benzyl-6alpha-chloro-6beta-carbonitrile-2,2-ethylgnedioxy-8-azabicyclo[3.2.1]oct-3-ene (8) and its C(6) epimer (9) were hydrolyzed to afford 6-ketone (10). Reduction of the ketone (10) with sodium borohydride gave predominantly 6alpha-ol (14). 2-Ketone (20), obtained from 14 by deprotection followed by hydrogenation and acetylation, was reduced with sodium borohydride to give 2beta-ol a as the major epimer. Nortropane (24) was prepared from 21 by debenzylation.

  DOI：

  10.3987/com-93-6480