trans-1,2-dinitrospiropentane | 136476-35-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: trans-1,2-dinitrospiropentane
• CAS: 136476-35-2
• 化学式: C₅H₆N₂O₄
• 分子量: 158.114
• InChiKey: COASIVSTEZBVPU-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 trans-1,2-dinitrospiropentane 在 lithium diisopropyl amide 作用下， 生成 [(1S,2R)-2-(Hydroxy-phenyl-methyl)-1,2-dinitro-spiro[2.2]pent-1-yl]-phenyl-methanol
  参考文献：
  名称：

  Polynitro-substituted strained-ring compounds. 2. 1,2-Dinitrospiropentanes

  摘要：

  trans-1,2-Dinitrospiropentane was prepared in 43% yield from 1,1-bis(nitromethyl)cyclopropane, best obtained by dry-phase ozonolysis of the corresponding diamine. The structure of trans- 1,2-dinitrospiropentane was assigned on the basis of spectroscopic data, elemental analysis, and X-ray crystallographic data. The first pK(a) was determined to be 18.6-21.6 in DMSO solution with decomposition. Reaction of trans- 1,2-dinitrospiropentane with sodium methoxide and iodine gave a mixture of iodinated spiropentanes, from which, cis- and trans-1,2-diiodo-1,2-dinitrospiropentane could be isolated in pure form. These diiodides were stable at room temperature but gave off iodine upon melting at 150-160-degrees-C. Treatment with sodium thiosulfate in aqueous DMSO solution gave back the deiodinated dinitro compound. trans-1,2-Dinitrospiropentane reacted with lithium diisopropylamide and benzaldehyde in THF to afford a bis(nitroaldol) product in 59% yield.

  DOI：

  10.1021/ja00023a031
• 作为产物：
  描述：

  1,1-环丙基二羧酸 在 吡啶 、 sodium azide 、 硼烷四氢呋喃络合物 、 碘 、 silica gel 、 dimsyl sodium 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 48.82h， 生成 trans-1,2-dinitrospiropentane
  参考文献：
  名称：

  Polynitro-substituted strained-ring compounds. 2. 1,2-Dinitrospiropentanes

  摘要：

  trans-1,2-Dinitrospiropentane was prepared in 43% yield from 1,1-bis(nitromethyl)cyclopropane, best obtained by dry-phase ozonolysis of the corresponding diamine. The structure of trans- 1,2-dinitrospiropentane was assigned on the basis of spectroscopic data, elemental analysis, and X-ray crystallographic data. The first pK(a) was determined to be 18.6-21.6 in DMSO solution with decomposition. Reaction of trans- 1,2-dinitrospiropentane with sodium methoxide and iodine gave a mixture of iodinated spiropentanes, from which, cis- and trans-1,2-diiodo-1,2-dinitrospiropentane could be isolated in pure form. These diiodides were stable at room temperature but gave off iodine upon melting at 150-160-degrees-C. Treatment with sodium thiosulfate in aqueous DMSO solution gave back the deiodinated dinitro compound. trans-1,2-Dinitrospiropentane reacted with lithium diisopropylamide and benzaldehyde in THF to afford a bis(nitroaldol) product in 59% yield.

  DOI：

  10.1021/ja00023a031