Bicyclo[10.3.1]hexadeca-1(16),12,14-trien-3,9-diyne | 195448-60-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: Bicyclo[10.3.1]hexadeca-1(16),12,14-trien-3,9-diyne
• CAS: 195448-60-3
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: POWXABFEIKZVMA-UHFFFAOYSA-N

物化性质

• 沸点：
  354.8±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  Bicyclo[10.3.1]hexadeca-1(16),12,14-trien-3,9-diyne 在 potassium tert-butylate 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  Syntheses and Properties of Medium-Sized Metacyclophanediynes

  摘要：

  The syntheses of [11]metacyclophane-2,9-diyne (3), [4.4]metacyclophane-2,12-diyne (4), [4.4]orthometacyclophane-2,12-diyne (5), (Z)-[10]metacyclophane-5-ene-2,8-diyne (6), [10]metacyclophane-2,8-diyne (7), and 5-isopropylidene[9]metacyclophane-2,7-diyne (8) have been achieved. The systems could be stabilized by protecting the triple bonds in 3-8 with the Co-2(CO)(6) moiety. PE spectroscopic investigations of 3 and 6-8 gave no clear-cut evidence for homoconjugative interactions among the pi fragments. The triple bonds in 3-8 could be transformed into the corresponding cis double bands by applying 2-5 molar equiv of Schwartz's reagent (28). Treatment of 3, 4, and ? with t-BuOK allows the transformation of the propargylic moieties into allenic moieties, whereas the same treatment of 5 and 6 transforms the 2-butynyl bridges into 1,3-butadiene bridges, giving rise to several isomers. The structural assignments of 3-8 and their reaction products are based an their spectroscopic properties.

  DOI：

  10.1021/jo970327r
• 作为产物：
  描述：

  1,7-辛二炔 、 1,3-二(碘甲基)苯 在 正丁基锂 作用下， 生成 Bicyclo[10.3.1]hexadeca-1(16),12,14-trien-3,9-diyne
  参考文献：
  名称：

  Syntheses and Properties of Medium-Sized Metacyclophanediynes

  摘要：

  The syntheses of [11]metacyclophane-2,9-diyne (3), [4.4]metacyclophane-2,12-diyne (4), [4.4]orthometacyclophane-2,12-diyne (5), (Z)-[10]metacyclophane-5-ene-2,8-diyne (6), [10]metacyclophane-2,8-diyne (7), and 5-isopropylidene[9]metacyclophane-2,7-diyne (8) have been achieved. The systems could be stabilized by protecting the triple bonds in 3-8 with the Co-2(CO)(6) moiety. PE spectroscopic investigations of 3 and 6-8 gave no clear-cut evidence for homoconjugative interactions among the pi fragments. The triple bonds in 3-8 could be transformed into the corresponding cis double bands by applying 2-5 molar equiv of Schwartz's reagent (28). Treatment of 3, 4, and ? with t-BuOK allows the transformation of the propargylic moieties into allenic moieties, whereas the same treatment of 5 and 6 transforms the 2-butynyl bridges into 1,3-butadiene bridges, giving rise to several isomers. The structural assignments of 3-8 and their reaction products are based an their spectroscopic properties.

  DOI：

  10.1021/jo970327r

文献信息

• Syntheses and Properties of Medium-Sized Metacyclophanediynes
  作者：Matthias Ramming、Rolf Gleiter

  DOI：10.1021/jo970327r

  日期：1997.8.1

  The syntheses of [11]metacyclophane-2,9-diyne (3), [4.4]metacyclophane-2,12-diyne (4), [4.4]orthometacyclophane-2,12-diyne (5), (Z)-[10]metacyclophane-5-ene-2,8-diyne (6), [10]metacyclophane-2,8-diyne (7), and 5-isopropylidene[9]metacyclophane-2,7-diyne (8) have been achieved. The systems could be stabilized by protecting the triple bonds in 3-8 with the Co-2(CO)(6) moiety. PE spectroscopic investigations of 3 and 6-8 gave no clear-cut evidence for homoconjugative interactions among the pi fragments. The triple bonds in 3-8 could be transformed into the corresponding cis double bands by applying 2-5 molar equiv of Schwartz's reagent (28). Treatment of 3, 4, and ? with t-BuOK allows the transformation of the propargylic moieties into allenic moieties, whereas the same treatment of 5 and 6 transforms the 2-butynyl bridges into 1,3-butadiene bridges, giving rise to several isomers. The structural assignments of 3-8 and their reaction products are based an their spectroscopic properties.