1,1-bis(azidomethyl)cyclopropane | 136476-39-6

• 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: 1,1-bis(azidomethyl)cyclopropane
• 英文别名: 1,1-Di-(azidomethyl)-cyclopropan
• CAS: 136476-39-6
• 化学式: C₅H₈N₆
• 分子量: 152.159
• InChiKey: HJDGIJBUUNHCFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-bis(azidomethyl)cyclopropane 在 碘 、 sodium methylate 、 silica gel 、 dimsyl sodium 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.32h， 生成 (S)-1-Iodo-1,2-dinitro-spiro[2.2]pentane
  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 作用下， 以 二甲基亚砜 为溶剂， 反应 33.0h， 生成 1,1-bis(azidomethyl)cyclopropane
  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

• PYRIMIDINONE DERIVATIVES, PREPARATION THEREOF AND PHARMACEUTICAL USE THEREOF
  申请人：Arigon Jerome

  公开号：US20130289031A1

  公开（公告）日：2013-10-31

  The invention relates to novel products of formula (Ia) or (Ib): these products being in all the isomeric forms and salts as drugs, notably as anticancer drugs.

  这项发明涉及公式(Ia)或(Ib)的新产品：这些产品以所有同分异构体和盐的形式作为药物，特别是作为抗癌药物。