(R,R)-2,2-dideuterio-1,3-bis[(E)-2-ethoxycarbonylethenyl]cyclopropane | 883223-47-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,R)-2,2-dideuterio-1,3-bis[(E)-2-ethoxycarbonylethenyl]cyclopropane
• CAS: 883223-47-0
• 化学式: C₁₃H₁₈O₄
• 分子量: 240.268
• InChiKey: ZQLSQQRAFQKRAS-HIFADNSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R,R)-2,2-dideuterio-1,3-bis[(E)-2-ethoxycarbonylethenyl]cyclopropane 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(R,R)-2,2-dideuterio-1,3-bis[(E)-3-hydroxy-1-propen-1-yl]cyclopropane
  参考文献：
  名称：

  Helical Structure of Tercyclopropanedimethanol in Solution

  摘要：

  Oligocyclopropanes with repetitive stereochemistry occur in two unusual natural products with interesting bioactivity. X-ray crystal structures are available for these compounds but with partially contradicting results. Because the H-1 and C-13 NMR spectra of oligocycloproparies are far from trivial to be assigned even at highest magnetic fields, we have prepared a specifically deuterated sample and have applied high field NMR spectroscopy and DFr calculations to determine its conformation. The helix with equal handedness shown in the stereopicture was found for tercyclopropanedimethanol. A dihedral angle of around +40 degrees is the best representation of the experimental data and characterizes, therefore, the dominating helical conformation of tercyclopropanedimethanol with a single repetitive (+)-gauche interunit dihedral angle. This is in full agreement with the crystal structure of the all sun,trans-quinquecyclopropanedimethanol with an R configuration at the termini that also adopted an all (+)-gauche conformation. However, the crystal structure of the title compound and the solution structure are different.

  DOI：

  10.1021/jo0525985
• 作为产物：
  描述：

  (R,R)-2,2-dideuterio-1,3-cyclopropanedimethanol 、 乙氧甲酰基亚甲基三苯基膦 在 吡啶 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 二甲基亚砜 、 乙醚 为溶剂， 以60%的产率得到(R,R)-2,2-dideuterio-1,3-bis[(E)-2-ethoxycarbonylethenyl]cyclopropane
  参考文献：
  名称：

  Helical Structure of Tercyclopropanedimethanol in Solution

  摘要：

  Oligocyclopropanes with repetitive stereochemistry occur in two unusual natural products with interesting bioactivity. X-ray crystal structures are available for these compounds but with partially contradicting results. Because the H-1 and C-13 NMR spectra of oligocycloproparies are far from trivial to be assigned even at highest magnetic fields, we have prepared a specifically deuterated sample and have applied high field NMR spectroscopy and DFr calculations to determine its conformation. The helix with equal handedness shown in the stereopicture was found for tercyclopropanedimethanol. A dihedral angle of around +40 degrees is the best representation of the experimental data and characterizes, therefore, the dominating helical conformation of tercyclopropanedimethanol with a single repetitive (+)-gauche interunit dihedral angle. This is in full agreement with the crystal structure of the all sun,trans-quinquecyclopropanedimethanol with an R configuration at the termini that also adopted an all (+)-gauche conformation. However, the crystal structure of the title compound and the solution structure are different.

  DOI：

  10.1021/jo0525985