(1S,5S)-bicyclo[3.3.1]non-3-ene-2,8-dione | 866327-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5S)-bicyclo[3.3.1]non-3-ene-2,8-dione
• CAS: 866327-28-8
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: PIBNDMAKULHYES-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,5S)-bicyclo[3.3.1]non-3-ene-2,8-dione 、 乙醇 在 sodium ethanolate 作用下， 反应 0.75h， 以88%的产率得到(R)-ethyl 3-(4-oxocyclohex-2-enyl)propionate
  参考文献：
  名称：

  Organocatalytic Entry to Chiral Bicyclo[3.n.1]alkanones via Direct Asymmetric Intramolecular Aldolization

  摘要：

  The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and endo-7-hydroxybicyclo[3.2.1]octan-2-one, featuring an alpha-amino acid catalyzed intramolecular aldolization of sigma-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaidehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1]nonan-2-one.

  DOI：

  10.1021/ol051569d
• 作为产物：
  描述：

  (1S,5R,8R)-8-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.3.1]nonan-2-one 在 四丁基氟化铵 、 戴斯-马丁氧化剂 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 38.0h， 生成 (1S,5S)-bicyclo[3.3.1]non-3-ene-2,8-dione
  参考文献：
  名称：

  Organocatalytic Entry to Chiral Bicyclo[3.n.1]alkanones via Direct Asymmetric Intramolecular Aldolization

  摘要：

  The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and endo-7-hydroxybicyclo[3.2.1]octan-2-one, featuring an alpha-amino acid catalyzed intramolecular aldolization of sigma-symmetric substrates, are described. A high enantioselectivity and a high catalytic efficiency have been exhibited by (4R,2S)-tetrabutylammonium 4-TBDPSoxy-prolinate in the aldolization of 3-(4-oxocyclohexyl)propionaidehyde to give highly enantiomerically enriched (1S,5R,8R)-8-hydroxybicyclo[3.3.1]nonan-2-one.

  DOI：

  10.1021/ol051569d