4-(2',2'-dibromocyclopropyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane | 202720-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2',2'-dibromocyclopropyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane
• 英文别名: 4-(2,2-Dibromocyclopropyl)-5-ethenyl-2,2-dimethyl-1,3-dioxolane
• CAS: 202720-00-1
• 化学式: C₁₀H₁₄Br₂O₂
• 分子量: 326.028
• InChiKey: CLRLILDZTXBOSM-UHFFFAOYSA-N

物化性质

• 沸点：
  306.2±42.0 °C(Predicted)
• 密度：
  1.770±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2',2'-dibromocyclopropyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane 在 二甲基硫 、 甲基锂 、 臭氧 作用下， 生成 cis-tricyclo[4.1.0.0^1,3]heptane-4,5-diol acetonide
  参考文献：
  名称：

  Synthesis, Reactions, and Structural Studies of Two-Carbon Bridged Spiropentanes

  摘要：

  The syntheses of three 4,5-disubstituted derivatives of tricyclo[4.1.0.0(1,3)]heptane (3) are reported. The relative stereochemistry of the oxygen substituents in these compounds was deduced by C-13 NMR spectroscopy and unequivocally confirmed by single-crystal X-ray analysis of the thiocarbonate derivative 15, The experimental results obtained from reaction of the 2,4-diol 6 under Swern conditions and with TPAP were explained by the results of ab initio calculations at the MP2/6-31G* level of theory.

  DOI：

  10.1021/jo970972y
• 作为产物：
  描述：

  1,5-己二烯-3,4-二醇 在 sodium hydroxide 、 二苯并-18-冠醚-6 、 频哪醇 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 56.0h， 生成 4-(2',2'-dibromocyclopropyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis, Reactions, and Structural Studies of Two-Carbon Bridged Spiropentanes

  摘要：

  The syntheses of three 4,5-disubstituted derivatives of tricyclo[4.1.0.0(1,3)]heptane (3) are reported. The relative stereochemistry of the oxygen substituents in these compounds was deduced by C-13 NMR spectroscopy and unequivocally confirmed by single-crystal X-ray analysis of the thiocarbonate derivative 15, The experimental results obtained from reaction of the 2,4-diol 6 under Swern conditions and with TPAP were explained by the results of ab initio calculations at the MP2/6-31G* level of theory.

  DOI：

  10.1021/jo970972y

文献信息

• Synthesis, Reactions, and Structural Studies of Two-Carbon Bridged Spiropentanes
  作者：Kenneth B. Wiberg、John R. Snoonian

  DOI：10.1021/jo970972y

  日期：1998.3.1

  The syntheses of three 4,5-disubstituted derivatives of tricyclo[4.1.0.0(1,3)]heptane (3) are reported. The relative stereochemistry of the oxygen substituents in these compounds was deduced by C-13 NMR spectroscopy and unequivocally confirmed by single-crystal X-ray analysis of the thiocarbonate derivative 15, The experimental results obtained from reaction of the 2,4-diol 6 under Swern conditions and with TPAP were explained by the results of ab initio calculations at the MP2/6-31G* level of theory.