(4-Iodocubyl)acetylene | 134971-14-5

• 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
• 英文名称: (4-Iodocubyl)acetylene
• 英文别名: 1-Ethynyl-4-iodocubane
• CAS: 134971-14-5
• 化学式: C₁₀H₇I
• 分子量: 254.07
• InChiKey: KGOXGAGWPGZOQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-溴-2,4-二硝基苯 、 (4-Iodocubyl)acetylene 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 16.0h， 以51%的产率得到
  参考文献：
  名称：

  古巴交叉耦合和古巴卟啉阵列

  摘要：

  本文报道了一种改进的芳基-古巴交叉偶联方法。分析了古巴核的特殊性及其在交叉耦合条件下的行为，同时通过各种芳基-古巴体系的合成，包括古巴和卟啉的偶联产物，证明了这种适应性的Baran交叉耦合方法的多功能性。此外，还展示了Sonogashira反应对炔基-古巴酮的臂延伸，这显示了在钯催化剂存在下，古巴尼核心的稳定性的第一个证据。

  DOI：

  10.1002/chem.201704344
• 作为产物：
  描述：

  1-iodo-4-(2,2-dibromovinyl)cubane 在 盐酸 、 甲基锂 作用下， 生成 (4-Iodocubyl)acetylene
  参考文献：
  名称：

  Alkynylcubanes as Precursors of Rigid-Rod Molecules and Alkynylcyclooctatetraenes

  摘要：

  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.

  DOI：

  10.1021/ja00096a016

文献信息

• Synthesis of alkynylcyclooctatetraenes and alkynylcubanes
  作者：Philip E. Eaton、Daniel Stossel

  DOI：10.1021/jo00017a028

  日期：1991.8

  The couplings of a variety of iodocubanes with terminal acetylenes in refluxing NEt3 in the presence of Cu(I) and Pd(0) were examined. The products, isolated in about 50% yield, were not alkynylcubanes but were instead the first examples of alkynyl-1,3,5,7-cyclooctatetraenes. The first examples of alkynylcubanes (cubylacetylenes) were themselves synthesized in modest yield by Negishi's procedure from alkyl cubyl ketones. Cubylacetylenes were shown to be stable under Heck-like coupling conditions and potentially useful thereby for the introduction of the cubylacetylene moiety into complex systems.
• 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：——
• 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.
• Cubane Cross-Coupling and Cubane-Porphyrin Arrays
  作者：Stefan S. R. Bernhard、Gemma M. Locke、Shane Plunkett、Alina Meindl、Keith J. Flanagan、Mathias O. Senge

  DOI：10.1002/chem.201704344

  日期：2018.1.24

  Herein, an improved methodology for aryl‐cubane cross‐coupling is reported. The peculiarities of the cubane core and its behavior during cross‐coupling conditions were analyzed, while the versatility of this adapted Baran cross‐coupling methodology was demonstrated by the synthesis of various aryl‐cubane systems, including coupling products of cubanes and porphyrins. Furthermore, arm extension of alkynyl‐cubanes

  本文报道了一种改进的芳基-古巴交叉偶联方法。分析了古巴核的特殊性及其在交叉耦合条件下的行为，同时通过各种芳基-古巴体系的合成，包括古巴和卟啉的偶联产物，证明了这种适应性的Baran交叉耦合方法的多功能性。此外，还展示了Sonogashira反应对炔基-古巴酮的臂延伸，这显示了在钯催化剂存在下，古巴尼核心的稳定性的第一个证据。