1-(2,2-dimethyl-propionyloxy)-4-oxo-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-7-carboxylic acid ethyl ester | 1141938-49-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(2,2-dimethyl-propionyloxy)-4-oxo-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-7-carboxylic acid ethyl ester
• 英文别名: ethyl (1S,4aS,7aS)-1-(2,2-dimethylpropanoyloxy)-4-oxo-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-carboxylate
• CAS: 1141938-49-9
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: AIAINKMEBJSRBB-LQJRIPTKSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  417.5±45.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 1-(2,2-dimethyl-propionyloxy)-4-oxo-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-7-carboxylic acid ethyl ester 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Iridoid β-Glucoside (+)-Geniposide via Phosphine Organocatalysis

  摘要：

  Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2,3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the cis-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.

  DOI：

  10.1021/ol900360h
• 作为产物：
  描述：

  2,3-丁二烯酸乙酯 、 2,2-dimethyl-propionic acid 5-oxo-5,6-dihydro-2H-pyran-2-yl ester 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以63%的产率得到1-(2,2-dimethyl-propionyloxy)-4-oxo-1,3,4,4a,5,7a-hexahydro-cyclopenta[c]pyran-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Iridoid β-Glucoside (+)-Geniposide via Phosphine Organocatalysis

  摘要：

  Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2,3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the cis-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.

  DOI：

  10.1021/ol900360h

文献信息

• Asymmetric Total Synthesis of the Iridoid β-Glucoside (+)-Geniposide via Phosphine Organocatalysis
  作者：Regan A. Jones、Michael J. Krische

  DOI：10.1021/ol900360h

  日期：2009.4.16

  Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2,3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the cis-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.