cis-1,2-diiodo-1,2-dinitrospiropentane | 136476-42-1

• 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: cis-1,2-diiodo-1,2-dinitrospiropentane
• 英文别名: (1R,2S)-1,2-diiodo-1,2-dinitrospiro[2.2]pentane
• CAS: 136476-42-1
• 化学式: C₅H₄I₂N₂O₄
• 分子量: 409.907
• InChiKey: LSCQPAUFNVJLCR-SYDPRGILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13.0
• 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：

  cis-1,2-diiodo-1,2-dinitrospiropentane 在 sodium thiosulfate 、 lithium diisopropyl amide 作用下， 以 二甲基亚砜 为溶剂， 反应 4.11h， 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 、 三丁基膦 、 碘 、 sodium methylate 、 dimsyl sodium 、 臭氧 作用下， 以 二甲基亚砜 为溶剂， 反应 35.15h， 生成 cis-1,2-diiodo-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

文献信息

• Trapping evidence for 1,2-dinitrospiropentene
  作者：Peter A. Wade、Paul A. Kondracki

  DOI：10.1039/c39940001263

  日期：——

  Photolysis of 1,2-diiodo-1,2-dinitrospiropentanes 1a and/or 1b in the presence of furan afforded the formal Diels–Alder adduct 2 of 1,2-dinitrospiropentene.

  在呋喃存在下，1,2-二碘-1,2-二硝基螺戊烷1a和/或1b的光解反应产生了1,2-二硝基螺戊烯的Diels-Alder加成物2。
• Wade Peter A., Kondracki Paul A., J. Chem. Soc. Chem. Commun, (1994) N 10, S 1263-1264
  作者：Wade Peter A., Kondracki Paul A.

  DOI：——

  日期：——