1,3,5,7-Tetracarbomethoxycubane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,5,7-Tetracarbomethoxycubane
• 英文别名: Tetramethyl cubane-1,3,5,7-tetracarboxylate
• 化学式: C₁₆H₁₆O₈
• 分子量: 336.298
• InChiKey: HBUIPHRDGCECJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,5,7-Tetracarbomethoxycubane 在 草酰氯 作用下， 反应 48.0h， 以28%的产率得到2-Chloro-1,3,5,7-tetracarbomethoxycubane
  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：

  甲醇 、 草酰氯 、 1-立方烷羧酸 生成 1,2,4,7-Tetracarbomethoxycubane 、 1,2,3,5,7-Penta(carboxymethyl)cubane 、 1,3,5,7-Tetracarbomethoxycubane 、 1,2,3,7-Tetracarbomethoxycubane
  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

文献信息

• 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 .
• US6635131B2
  申请人：——

  公开号：US6635131B2

  公开（公告）日：2003-10-21