7-acetoxymethyl-1-(2,2-dimethyl-propionyloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester | 1141938-57-9

• 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: 7-acetoxymethyl-1-(2,2-dimethyl-propionyloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
• CAS: 1141938-57-9
• 化学式: C₁₈H₂₄O₇
• 分子量: 352.384
• InChiKey: VURQNCHAAZEREI-XPKDYRNWSA-N

物化性质

• 熔点：
  71-72 °C
• 沸点：
  438.8±45.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  7-acetoxymethyl-1-(2,2-dimethyl-propionyloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 在 甲醇 、 1,3-dichloro-1,1,3,3-tetrabutylstannoxane 作用下， 以 甲苯 为溶剂， 以73%的产率得到7-(2,2-dimethyl-propionyloxymethyl)-1-hydroxy-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl 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
• 作为产物：
  描述：

  7-acetoxymethyl-1-(2,2-dimethyl-propionyloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 、 氯仿 为溶剂， 生成 7-acetoxymethyl-1-(2,2-dimethyl-propionyloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl 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