1,2,3,5,7-Penta(carboxymethyl)cubane

• 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: 1,2,3,5,7-Penta(carboxymethyl)cubane
• 英文别名: Pentamethyl cubane-1,2,3,5,7-pentacarboxylate；pentamethyl cubane-1,2,3,5,7-pentacarboxylate
• 化学式: C₁₈H₁₈O₁₀
• 分子量: 394.335
• InChiKey: KTSAUVXCFBDTQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 水 作用下， 生成 cubane-1,3,5,7-tetracarboxylic acid 、 1,2,3,5,7-Penta(carboxymethyl)cubane
  参考文献：
  名称：

  Bashir-Hashemi, A., Angewandte Chemie, 1993, vol. 105, # 4, p. 585 - 586

  摘要：

  DOI：

文献信息

• Photochemical Functionalization of Cubanes
  作者：A. Bashir-Hashemi、J. Li、Nathan Gelber、Herman Ammon

  DOI：10.1021/jo00108a037

  日期：1995.2

  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.
• Bashir-Hashemi, A., Angewandte Chemie, 1993, vol. 105, # 4, p. 585 - 586
  作者：Bashir-Hashemi, A.

  DOI：——

  日期：——