2,2-dimethyl-propionic acid 4-carbamoyl-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yl ester | 1141938-56-8

• 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: 2,2-dimethyl-propionic acid 4-carbamoyl-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yl ester
• CAS: 1141938-56-8
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: HOHRWHLDRRRLIG-XWIASGKRSA-N

物化性质

• 熔点：
  154-155 °C (decomp)
• 沸点：
  494.2±45.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  98.85
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-propionic acid 4-carbamoyl-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yl ester 、 乙酸酐 在 三乙胺 作用下， 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：

  2,2-dimethyl-propionic acid 4-cyano-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yl ester 在 hydrido(dimethylphosphinous acid-κP)[hydrogen bis(dimethylphosphinito-κP)]platinum(II) 、 水 作用下， 以 乙醇 为溶剂， 以87%的产率得到2,2-dimethyl-propionic acid 4-carbamoyl-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yl 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