cyclohexanone ketal of cis-1,2-bis(hydroxymethyl)cyclopropane | 124200-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexanone ketal of cis-1,2-bis(hydroxymethyl)cyclopropane
• 英文别名: piro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octane]
• CAS: 124200-36-8
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: UKBKDRGDSWYWRS-AOOOYVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cyclohexanone ketal of cis-1,2-bis(hydroxymethyl)cyclopropane 在 水 、 溶剂黄146 作用下， 反应 24.0h， 以85%的产率得到[(1S,2R)-rel-2-(羟甲基)环丙基]甲醇
  参考文献：
  名称：

  Secondary deuterium kinetic isotope effects at the termini of cis-1,2-divinylcyclopropane and cis-1,2-divinylcyclobutane in their 3,3-sigmatropic shifts: evidence for different transition-state structures

  摘要：

  DOI：

  10.1021/jo00289a050
• 作为产物：
  描述：

  环丙烷-1,2-二羧酸二甲酯 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 20.0h， 生成 cyclohexanone ketal of cis-1,2-bis(hydroxymethyl)cyclopropane
  参考文献：
  名称：

  Secondary deuterium kinetic isotope effects at the termini of cis-1,2-divinylcyclopropane and cis-1,2-divinylcyclobutane in their 3,3-sigmatropic shifts: evidence for different transition-state structures

  摘要：

  DOI：

  10.1021/jo00289a050

文献信息

• Stereochemistry of seven-membered heterocycles: XLVI. Synthesis and dynamic 13C NMR spectroscopy of spiro[cyclohexane-1,4′-[3,5]dioxabicyclo[5.1.0]octanes]. DFT calculations of structurally related formaldehyde and acetone acetals
  作者：V. V. Gavrilov、M. N. Shamsutdinov、G. A. Chmutova、R. M. Vafina、Yu. G. Shtyrlin、V. V. Klochkov、E. N. Klimovitskii

  DOI：10.1134/s1070428007120196

  日期：2007.12

  Spiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octanes] were synthesized, and their conformational behavior was studied by dynamic C-13 NMR spectroscopy. Anancomeric displacement of conformational equilibrium toward two nonequivalent twist conformers with close energies was revealed. The relative Gibbs energies Delta G degrees and enthalpies of formation Delta H degrees of twist and chair-like conformers with endo and exo orientation of the three-membered ring of structurally related formaldehyde and acetone acetals were calculated in terms of the density functional theory at the B3LYP/6-31G(d,p) level. Like spiro-cyclohexane analogs, they were shown to have a non-chair conformation.