3,7-Dichloro-3,7-dinitrobicyclo<3.3.1>nonane | 131296-17-8

• 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: 3,7-Dichloro-3,7-dinitrobicyclo<3.3.1>nonane
• 英文别名: 3,7-Dichloro-3,7-dinitrobicyclo[3.3.1]nonane
• CAS: 131296-17-8
• 化学式: C₉H₁₂Cl₂N₂O₄
• 分子量: 283.111
• InChiKey: DBFKSLKIYVJTBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sode de l'acide trichloroisocyanurique 、 丙酮肟 、 3,7-Dichloro-3,7-dinitrobicyclo<3.3.1>nonane 、 碳酸氢钠 生成 2-硝基-2-氯丙烷
  参考文献：
  名称：

  WALTERS, THOMAS R.;ZAJAC, WALTER W. (JR);WOODS, JAMES M., J. ORG. CHEM., 56,(1991) N, C. 316-321

  摘要：

  DOI：
• 作为产物：
  描述：

  Bicyclo<3.3.1>nonan-3,7-dion-dioxim 在 sode de l'acide trichloroisocyanurique 、 碳酸氢钠 、 臭氧 作用下， 生成 3,7-Dichloro-3,7-dinitrobicyclo<3.3.1>nonane
  参考文献：
  名称：

  New reagents for the synthesis of gem-halonitro compounds from oximes

  摘要：

  The utility of the N-haloheterocycles 1-sodio-3,5-dichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (4), 1,3,5-trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (5), 1,3-dibromo-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (6), and 1,3-dibromo-5,5-dimethylhydantoin (7) for the halogenation-oxidation of oximes to gem-halonitro compounds is reported. The triazine derivatives 4, 5, and 6 provided satisfactory yields when employed either alone or in combination with ozone as a supplemental oxidant. Hydantoin 7 required the use of a supplemental oxidant. The yields for the reactions were consistently 70% for simple oximes and 50% for molecules possessing two oxime functions. Occasional difficulties were encountered in reproducing the yields of the products from the bromination-oxidation sequence. The formation of modest amounts (20-30%) of 3,7-dinitronoradamantane via cyclization was observed in the reactions of bicyclo[3.3.1]nonane-3,7-dione dioxime.

  DOI：

  10.1021/jo00001a059