1,6-Bis(1-adamantyl)-1,3,5-hexatriyne | 259546-37-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 1,6-Bis(1-adamantyl)-1,3,5-hexatriyne
• 英文别名: 1-[6-(1-Adamantyl)hexa-1,3,5-triynyl]adamantane；1-[6-(1-adamantyl)hexa-1,3,5-triynyl]adamantane
• CAS: 259546-37-7
• 化学式: C₂₆H₃₀
• 分子量: 342.524
• InChiKey: LASVLJNZOGRCBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  1,6-Bis(1-adamantyl)-1,3,5-hexatriyne 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 以41%的产率得到2-(1-Adamantyl)-3-[4-(1-adamantyl)buta-1,3-diynyl]-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes

  摘要：

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.

  DOI：

  10.1021/ja049836i
• 作为产物：
  描述：

  1-乙炔基金刚烷 在 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 silver nitrate 、 正丁胺 、 copper(l) chloride 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 1,6-Bis(1-adamantyl)-1,3,5-hexatriyne
  参考文献：
  名称：

  Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes

  摘要：

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.

  DOI：

  10.1021/ja049836i

文献信息

• Evidence for Solution-State Nonlinearity of sp-Carbon Chains Based on IR and Raman Spectroscopy: Violation of Mutual Exclusion
  作者：Andrea Lucotti、Matteo Tommasini、Daniele Fazzi、Mirella Del Zoppo、Wesley A. Chalifoux、Michael J. Ferguson、Giuseppe Zerbi、Rik R. Tykwinski

  DOI：10.1021/ja078198b

  日期：2009.4.1

  violations of the mutual-exclusion principle between IR and Raman spectroscopy, spectral evidence demonstrates that these molecules possess a noncentrosymmetric molecular structure in both the solid and solution states. This premise is supported by X-ray crystallographic analysis of C12, which shows a bent, noncentrosymmetric structure in the solid state. Density functional theory (DFT) calculations

  已经合成了具有 4、6、8、10、12、16 和 20 sp 杂化碳 (C4-C20) 链的金刚烷基封端的聚炔，并获得了它们的红外和拉曼光谱。在违反 IR 和拉曼光谱之间的互斥原理的基础上，光谱证据表明这些分子在固体和溶液状态下都具有非中心对称的分子结构。这一前提得到了 C12 的 X 射线晶体学分析的支持，该分析显示出固态弯曲的非中心对称结构。与氢封端的聚炔相比，金刚烷基封端的聚炔的密度泛函理论 (DFT) 计算表明，观察到的互斥违反与聚炔链的端基无关（即，金刚烷基与H）。
• Mueller, Torsten; Hulliger, Juerg; Seichter, Wilhelm, Chemistry - A European Journal, 2000, vol. 6, # 1, p. 54 - 61
  作者：Mueller, Torsten、Hulliger, Juerg、Seichter, Wilhelm、Weber, Edwin、Weber, Thomas、Wuebbenhorst, Michael

  DOI：——

  日期：——
• Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes
  作者：May Xiao-Wu Jiang、Manish Rawat、William D. Wulff

  DOI：10.1021/ja049836i

  日期：2004.5.1

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.