1,4-dinitrocubane | 87830-30-6

• 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: 1,4-dinitrocubane
• CAS: 87830-30-6
• 化学式: C₈H₆N₂O₄
• 分子量: 194.147
• InChiKey: XNUFROJSYUVDEM-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C (decomp)
• 沸点：
  376.3±32.0 °C(Predicted)
• 密度：
  2.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  6.0
• 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：

  1,4-dinitrocubane 在 甲烷磺酸 作用下， 反应 18.0h， 生成 甲基2,7-二硝基立方烷-1-羧酸酯
  参考文献：
  名称：

  Photochemical Functionalization of Cubanes

  摘要：

  A wide range of cubanecarboxylic acids has been prepared by a simple and efficient photochemical process. Chlorocarbonylation of cubanecarboxylic acid with oxalyl chloride under UV irradiation produced polysubstituted cubanes with chlorocarbonyl groups predominantly on the remote sites (beta or gamma). The T-d-tetraacid chloride 6b, in which chlorocarbonyl groups are in alternate positions, was the major product. Irradiation of 1,2,3,7-tetrasubstituted cubane 9 with oxalyl chloride gave pentasubstituted cubane 10. Other isomers, 1,3,5,7-tetrasubstituted cubane 6 and 1,2,4,7-tetrasubstituted cubane 8, in which chlorocarbonylation would occur at positions ortho to three or two carbonyl groups, gave only chlorinated products. Photochemical reaction of oxalyl chloride with nitrocubanes gave chlorocarbonylated and chlorinated nitrocubanes. Ab initio calculations show carbon-hydrogen bond strength at different positions of the cubane is not the major factor in determining the regioselectivity of the chlorocarbonylation. A polar effect might be the key factor in site selectivity.

  DOI：

  10.1021/jo00108a037
• 作为产物：
  描述：

  1,4-diisocyanatocubane 在 二甲基二环氧乙烷 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以85%的产率得到1,4-dinitrocubane
  参考文献：
  名称：

  Conversion of isocyanates to nitro compounds with dimethyldioxirane in wet acetone

  摘要：

  DOI：

  10.1021/jo00257a030

文献信息

• Nitrocubanes
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US05235119A1

  公开（公告）日：1993-08-10

  An efficient direct functionalization of nitrocubanes has been achieved by irradiation of a solution in an oxalyl halide to yield halogenated and halocarbonylated derivatives of nitrocubanes.

  通过在草酸卤化物溶液中照射，实现了硝基立方烷的高效直接官能化反应，得到了卤代和卤代羰基化衍生物。
• Gas generating material for a vehicle occupant protection apparatus
  申请人：TRW Inc. and TRW Vehicle Safety Systems Inc.

  公开号：US20020135169A1

  公开（公告）日：2002-09-26

  An apparatus comprises a vehicle occupant protection device and a gas generating material, which, when ignited, produces gas to actuate the vehicle occupant protection device. The gas generating material comprises a cubane compound having the general formula: 1 wherein R is selected from the group consisting of H and NO 2 .

  一种装置包括车内乘员保护装置和气体发生材料，气体发生材料在点燃时产生气体以驱动车内乘员保护装置。气体发生材料包括具有通式的立方烷化合物： 1 其中 R 选自 H 和 NO 组成的组 2 .
• Chemistry of dioxiranes. 13. Oxidation of primary amines by dimethyldioxirane
  作者：Robert W. Murray、Shirish N. Rajadhyaksha、Lily Mohan

  DOI：10.1021/jo00285a027

  日期：1989.11
• Synthesis of 1,4-dinitrocubane
  作者：Philip E. Eaton、B. K. Ravi Shankar、Geoffrey D. Price、Joseph J. Pluth、Everett E. Gilbert、Jack Alster、Oscar Sandus

  DOI：10.1021/jo00175a044

  日期：1984.1
• MURRAY, ROBERT W.;RAJADHYAKSHA, SHIRISH N.;MOHAN, LILY, J. ORG. CHEM., 54,(1989) N4, C. 5783-5788
  作者：MURRAY, ROBERT W.、RAJADHYAKSHA, SHIRISH N.、MOHAN, LILY

  DOI：——

  日期：——