2-cyano-1,6-methano<10>annulene | 54004-10-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-1,6-methano<10>annulene
• 英文别名: Bicyclo[4.4.1]undeca-1(10),2,4,6,8-pentaene-2-carbonitrile
• CAS: 54004-10-3
• 化学式: C₁₂H₉N
• 分子量: 167.21
• InChiKey: AXRCCWSIPBGIMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  410.2±15.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine 、 2-cyano-1,6-methano<10>annulene 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以55%的产率得到1,4-Bis(trifluormethyl)-7,12-methanocyclodecapyridazin-8-carbonitril
  参考文献：
  名称：

  2-Substituierte 1,6-Methanol[10]annulene als Dienophile in der [4 + 2]-Cycloaddition mit inversem Elektronenbedarf

  摘要：

  The LUMO-diene-controlled [4 + 21 cycloadditions of various at C-2 substituted 1,6-methano [10]annulenes 6, 10 and 13 with the electron-deficient s-cis-fixed diazadiene system of 3,6-bis(trifluoro-methyl)-1,2,4,5-tetrazine (3) are described. With the donor substituted 6 (or its valence tautomer 7) 3 reacts under unusually mild conditions to give the 7,12-methanocyclodeca[d]pyridazine 9 with high site selectivity. The Diels-Alder reaction of 3 with the 2-bromo-1,6-methano[10]annulene (10 half arrow right over half arrow left 11) leads to the 6- and 8-bromo-7,12-methanocyclodeca[d]pyridazines 12 a and 12 b, whereas with the various acceptor substituted species 13 half arrow right over half arrow left 14 the 8-substituted 7,12-methanocyclodeca[d]pyridazines 15 a - c are formed exclusively. Spectroscopic data show, that for all the novel methanocyclodeca[d]pyridazines 9, 12 and 15 the annulenic structure is dominating, but a remarkable reduction of the ring current and a distinct bond alternation is observed compared to the parent 1,6-methano[10]annulene 1.

  DOI：

  10.1002/prac.19933350207
• 作为产物：
  描述：

  2-bromo-1,6-methano[10]annulene 、 氰化亚铜 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以88%的产率得到2-cyano-1,6-methano<10>annulene
  参考文献：
  名称：

  Applications of MCD spectroscopy: MO ordering and transannular interaction in 1,6-methano[10]annulenes from analysis of substituent effects

  摘要：

  DOI：

  10.1021/ja00349a001

文献信息

• Propellanes. LXVII. Reactions of 1, 6-bridged [10]annulenes with 4-methyl-1,2,4-triazoline-3, 5-dione
  作者：Pnina Ashkenazi、Emanuel Vogel、David Ginsburg

  DOI：10.1002/hlca.19830660222

  日期：1983.3.16

  Reactions of 11-substituted-1, 6-methano [10]annulenes and 1, 6-methano [10]-annulenes substituted in the aromatic ring with the title dienophile are described.

  描述了在芳族环中取代的11-取代的1,6-甲基[10]环和1,6-甲基[10]环与标题亲二烯体的反应。
• ASHKENZAI, P.;VOGEL, E.;GINSBURG, D., HELV. CHIM. ACTA, 1983, 66, N 2, 615-619
  作者：ASHKENZAI, P.、VOGEL, E.、GINSBURG, D.

  DOI：——

  日期：——
• Applications of MCD spectroscopy: MO ordering and transannular interaction in 1,6-methano[10]annulenes from analysis of substituent effects
  作者：Kenneth A. Klingensmith、Wilhelm Puettmann、Emanuel Vogel、Josef Michl

  DOI：10.1021/ja00349a001

  日期：1983.6
• 2-Substituierte 1,6-Methanol[10]annulene als Dienophile in der [4 + 2]-Cycloaddition mit inversem Elektronenbedarf
  作者：U. Reimers、G. Seitz

  DOI：10.1002/prac.19933350207

  日期：——

  The LUMO-diene-controlled [4 + 21 cycloadditions of various at C-2 substituted 1,6-methano [10]annulenes 6, 10 and 13 with the electron-deficient s-cis-fixed diazadiene system of 3,6-bis(trifluoro-methyl)-1,2,4,5-tetrazine (3) are described. With the donor substituted 6 (or its valence tautomer 7) 3 reacts under unusually mild conditions to give the 7,12-methanocyclodeca[d]pyridazine 9 with high site selectivity. The Diels-Alder reaction of 3 with the 2-bromo-1,6-methano[10]annulene (10 half arrow right over half arrow left 11) leads to the 6- and 8-bromo-7,12-methanocyclodeca[d]pyridazines 12 a and 12 b, whereas with the various acceptor substituted species 13 half arrow right over half arrow left 14 the 8-substituted 7,12-methanocyclodeca[d]pyridazines 15 a - c are formed exclusively. Spectroscopic data show, that for all the novel methanocyclodeca[d]pyridazines 9, 12 and 15 the annulenic structure is dominating, but a remarkable reduction of the ring current and a distinct bond alternation is observed compared to the parent 1,6-methano[10]annulene 1.