8',8'-dichlorospiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octane] | 1021166-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8',8'-dichlorospiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octane]
• CAS: 1021166-15-3
• 化学式: C₁₁H₁₆Cl₂O₂
• 分子量: 251.153
• InChiKey: QVAHFBPOLNLHAU-DTORHVGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  15.0
• 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：

  8',8'-dichlorospiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octane] 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 288.0h， 以81%的产率得到(1R,2S)-rel-3,3-dichloro-1,2-cyclopropanedimethanol
  参考文献：
  名称：

  七元杂环的立体化学：XLVI。螺[环己烷-1,4'-[3,5]二恶双环[5.1.0]辛烷]的合成及13 C NMR动态光谱。结构相关的甲醛和丙酮缩醛的DFT计算

  摘要：

  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.

  DOI：

  10.1134/s1070428007120196
• 作为产物：
  描述：

  7,12-二氧杂-螺[5.6]十二碳-9-烯 、 氯仿 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 水 为溶剂， 反应 169.0h， 以81%的产率得到8',8'-dichlorospiro[cyclohexane-1,4'-[3,5]dioxabicyclo[5.1.0]octane]
  参考文献：
  名称：

  七元杂环的立体化学：XLVI。螺[环己烷-1,4'-[3,5]二恶双环[5.1.0]辛烷]的合成及13 C NMR动态光谱。结构相关的甲醛和丙酮缩醛的DFT计算

  摘要：

  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.

  DOI：

  10.1134/s1070428007120196