4-(4-Azido-1-hydroxy-butyl)-3-methoxy-2-(1-methyl-2-oxo-propyl)-cyclopent-2-enone | 160626-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-Azido-1-hydroxy-butyl)-3-methoxy-2-(1-methyl-2-oxo-propyl)-cyclopent-2-enone
• CAS: 160626-99-3
• 化学式: C₁₄H₂₁N₃O₄
• 分子量: 295.338
• InChiKey: UDDOYQNKMFWSQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  112.36
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(4-Azido-1-hydroxy-butyl)-3-methoxy-2-(1-methyl-2-oxo-propyl)-cyclopent-2-enone 在 5%-palladium/activated carbon 吡啶 、 氨 、 氢气 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 、 乙腈 、 三氟乙酸 、 苯 为溶剂， 反应 50.0h， 生成 2,3-Dimethyl-6-pyrrolidin-(2Z)-ylidene-5,6-dihydro-1H-cyclopenta[b]pyrrol-4-one
  参考文献：
  名称：

  Dinoflagellate bioluminescence: The chromophore of dinoflagellate luciferin

  摘要：

  A concise synthesis of the chromophore proposed for dinoflagellate luciferin was accomplished. The chemical behavior towards molecular oxygen and spectroscopic characteristics of the synthetic chromophore were found to match well with those observed for dinoflagellate luciferin. Comparison of the C-13 chemical shifts observed for the E- and Z-isomers of the synthetic model with those observed for dinoflagellate luciferin suggested the natural luciferin to have an E-configuration about its C.15-C.16 olefinic bond.

  DOI：

  10.1016/s0040-4039(00)78538-8
• 作为产物：
  描述：

  3-羟基-2-环戊烯-1-酮 在 二甲基硫 、 臭氧 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 4-(4-Azido-1-hydroxy-butyl)-3-methoxy-2-(1-methyl-2-oxo-propyl)-cyclopent-2-enone
  参考文献：
  名称：

  Dinoflagellate bioluminescence: The chromophore of dinoflagellate luciferin

  摘要：

  A concise synthesis of the chromophore proposed for dinoflagellate luciferin was accomplished. The chemical behavior towards molecular oxygen and spectroscopic characteristics of the synthetic chromophore were found to match well with those observed for dinoflagellate luciferin. Comparison of the C-13 chemical shifts observed for the E- and Z-isomers of the synthetic model with those observed for dinoflagellate luciferin suggested the natural luciferin to have an E-configuration about its C.15-C.16 olefinic bond.

  DOI：

  10.1016/s0040-4039(00)78538-8