2,3-Dihydrodarlingine | 72362-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,3-Dihydrodarlingine
• 英文别名: 4,5,12-trimethyl-6-oxa-12-azatricyclo[7.2.1.02,7]dodec-2(7)-en-3-one
• CAS: 72362-48-2
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: NFKOVCVVWNXFIF-UHFFFAOYSA-N

物化性质

• 沸点：
  327.9±41.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-Dihydrodarlingine 在 ammonium hydroxide 、 copper(ll) bromide 作用下， 生成 (+/-)-darlingine
  参考文献：
  名称：

  Synthesis of pyranotropanes via enantioselective deprotonation strategy

  摘要：

  Synthesis of tropane alkaloids darlingine, chalcostrobamine and isobellendine both in the racemic form and as unnatural enantiomers is described. Enantioselective deprotonation of tropinone, which proceeded with ca 90% ee, was the key step in each of the syntheses. Enantioselectivity was increased in the presence of LiCl.

  DOI：

  10.1016/s0040-4039(00)73063-2
• 作为产物：
  描述：

  托品酮 、 tigloyl cyanide 在 sodium carbonate 、 lithium diisopropyl amide 作用下， 生成 2,3-Dihydrodarlingine
  参考文献：
  名称：

  Synthesis of pyranotropanes via enantioselective deprotonation strategy

  摘要：

  Synthesis of tropane alkaloids darlingine, chalcostrobamine and isobellendine both in the racemic form and as unnatural enantiomers is described. Enantioselective deprotonation of tropinone, which proceeded with ca 90% ee, was the key step in each of the syntheses. Enantioselectivity was increased in the presence of LiCl.

  DOI：

  10.1016/s0040-4039(00)73063-2

文献信息

• Synthesis of pyranotropanes via enantioselective deprotonation strategy
  作者：Marek Majewski、Ryszard Lazny

  DOI：10.1016/s0040-4039(00)73063-2

  日期：1994.5

  Synthesis of tropane alkaloids darlingine, chalcostrobamine and isobellendine both in the racemic form and as unnatural enantiomers is described. Enantioselective deprotonation of tropinone, which proceeded with ca 90% ee, was the key step in each of the syntheses. Enantioselectivity was increased in the presence of LiCl.