1,4-立方烷二甲醛 | 163332-89-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 1,4-立方烷二甲醛
• 英文名称: 1,4-cubanedicarboxaldehyde
• 英文别名: cubane-1,4-dicarboxaldehyde；cubane-1,4-dicarbaldehyde；Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde
• CAS: 163332-89-6
• 化学式: C₁₀H₈O₂
• 分子量: 160.172
• InChiKey: OHFPNYRQNMMOGT-UHFFFAOYSA-N

物化性质

• 沸点：
  263.4±40.0 °C(Predicted)
• 密度：
  2.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-立方烷二甲醛 以84%的产率得到
  参考文献：
  名称：

  Eaton Philip E., Galoppini Elena, Gilardi Richard, J. Amer. Chem. Soc, 116 (1994) N 17, S 7588-7596

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-双(羟甲基)立方烷 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 1,4-立方烷二甲醛
  参考文献：
  名称：

  通过古巴的价异构化环辛酸酯：范围和局限性

  摘要：

  在官能团耐受性，多重取代模式和古巴酒精经历一锅串联Ley-Griffith的能力的背景下，研究了伊顿铑（I）催化的古巴价氢异构化为环辛三烯（COT）的范围和局限性在没有过渡金属催化剂的情况下进行维蒂希反应。

  DOI：

  10.1002/chem.201805124

文献信息

• Synthesis of 4-bromocubane-1-carbaldehyde
  作者：A. V. Shastin、V. V. Zakharov、G. P. Bugaeva、L. T. Eremenko、L. B. Romanova、G. V. Lagodzinskaya、G. G. Aleksandrov、I. L. Eremenko

  DOI：10.1007/s11172-006-0416-7

  日期：2006.7

  loroisocyanuric acid-sodium bicarbonate system afforded the corresponding aldehydes. 4-Bromocubanecarbaldehyde was also obtained in high yield by reduction of 4-bromocubanecarboxylic acid and its methyl ester with bis(N-methylpiperazinyl)aluminum hydride.

  用 2,2,6,6-四甲基哌啶-N-氧基-三氯异氰尿酸-碳酸氢钠体系氧化 4-溴-1-羟甲基立方烷和 1,4-双（羟甲基）立方烷，得到相应的醛。通过用双（N-甲基哌嗪基）氢化铝还原 4-溴古巴羧酸及其甲酯，也可以高收率获得 4-溴古巴甲醛。
• Synthesis of 1,4-Annulated Cyclooctatetraenophanes Based on a Novel Cubane Building Block Approach
  作者：Robert M. Moriarty、Dražen Pavlović

  DOI：10.1021/jo049643d

  日期：2004.8.1

  approach to strained 1,4-annulated cyclooctatetraene-based cyclophanes is described. A key feature in this approach is exploitation of the cubane core as a masked cyclooctatetraene synthon. Thus, 1,4-disubstituted cubanes 3 and 4 used as precursors to cyclooctatetraenophanes have been prepared in four steps from the readily available 1,4-cubanedicarboxaldehyde (5). The synthesis of 3 was effected by pa

  描述了一种通用的合成方法，用于应变的1，4-环化的环辛酸酯基的环烷。该方法的关键特征是利用古巴核心作为掩蔽的环辛酸酯合成的合成子。因此，已经从容易获得的1，4-古巴二甲醛（5）分四个步骤制备了用作环辛酸酯/庚烷的前体的1，4-二取代古巴3和4。3的合成是通过钯/铜介导的1,4-双[（Z，Z）-2-碘乙烯基]古巴（6）和1,4-双[（Z，Z）-but-1）偶联而实现的-en-3-ynyl]古巴（8）。用于合成4另一方面，将改良的Eglington-Glaser耦合应用于大环化步骤。应用Rh（I）的一般特征来诱导古巴核心的[2 + 2]环还原为顺-三环[4.2.0.0 2,5 ]八-3,7-二烯，然后进行热重排为环辛三烯。结构转变为靶向环辛烯1和2。
• Alkynylcubanes as Precursors of Rigid-Rod Molecules and Alkynylcyclooctatetraenes
  作者：Philip E. Eaton、Elena Galoppini、Richard Gilardi

  DOI：10.1021/ja00096a016

  日期：1994.8

  We have developed new methodology for the synthesis of alkynylcubanes and have used these compounds to make rigid-rod molecules constructed of cubane and acetylene subunits. Terminal and substituted alkynylcubanes 7a, 7b, 8a, 8b, 12a, and 12b were synthesized by n-BuLi-promoted elimination of halogen from 1,1-dibromovinylcubanes 6a, 6b, and 11, followed by quenching with electrophiles. Systems with one or two acetylenic units between two cubanes were also prepared: dicubylacetylene (15) was obtained via reaction of the lithium ylide of (trimethylsilyl)diazomethane with dicubyl ketone (14); 1,4-dicubyl-1,3-butadiyne (16) was made by oxidative dimerization of ethynylcubane (7a). Dimerizations and cross-coupling reactions of various 1,4-diethynylcubanes afforded longer rods, e.g., 1,4-bis-((trimethylsilyl)ethynyl)cubyl- 1,3-butadiyne (18) and 1-(4-((trimethylsilyl)ethynyl)cubyl)-4-cubyl-1,3-butadiyne (21). Rh(I)-promoted ring opening of the cubane subunit(s) of these compounds into the corresponding tricyclooctadiene followed by thermal rearrangement to the cyclooctatetraene was used to convert 7a, 8a, and 12a into the mono- and disubstituted alkynylcyclooctatetraenes 22a, 22b, and 23 and to take 15 and 16 into the alkynyl-bridged cyclooctatetraenes 24a and 24b, respectively. X-ray crystallographic analysis of 12a, 15, 16, and 18 revealed interesting details about their structures.
• Eaton Philip E., Galoppini Elena, Gilardi Richard, J. Amer. Chem. Soc, 116 (1994) N 17, S 7588-7596
  作者：Eaton Philip E., Galoppini Elena, Gilardi Richard

  DOI：——

  日期：——
• Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations
  作者：Sevan D. Houston、Hui Xing、Paul V. Bernhardt、Timothy J. Vanden Berg、John Tsanaktsidis、G. Paul Savage、Craig M. Williams

  DOI：10.1002/chem.201805124

  日期：2019.2.21

  The scope and limitations of Eaton's rhodium(I)‐catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigated in the context of functional group tolerability, multiple substitution modes and the ability of cubane‐alcohols to undergo one‐pot tandem Ley–Griffith Wittig reactions in the absence of a transition metal catalyst.

  在官能团耐受性，多重取代模式和古巴酒精经历一锅串联Ley-Griffith的能力的背景下，研究了伊顿铑（I）催化的古巴价氢异构化为环辛三烯（COT）的范围和局限性在没有过渡金属催化剂的情况下进行维蒂希反应。