2-Isothiocyanato-1,6-methano<10>annulen | 115163-02-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 英文名称: 2-Isothiocyanato-1,6-methano<10>annulen
• 英文别名: 7-Isothiocyanatobicyclo[4.4.1]undeca-1,3,5,7,9-pentaene；2-isothiocyanatobicyclo[4.4.1]undeca-1(10),2,4,6,8-pentaene
• CAS: 115163-02-5
• 化学式: C₁₂H₉NS
• 分子量: 199.276
• InChiKey: RIMGCVSPMNMLDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  29 °C
• 沸点：
  439.8±28.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-azido-1,6-methano<10>annulene 以 乙醚 为溶剂， 反应 50.0h， 生成 2-Isothiocyanato-1,6-methano<10>annulen
  参考文献：
  名称：

  On the reaction of (vinylimino)phosphoranes and related compounds. 20. Syntheses and properties of methanocyclodeca[b]pyridine ring systems

  摘要：

  Novel 2-[(triphenyl- and 2-[(tributylphosphoranylidene)amino]-1,6-methanol[10]annulenes (8x,y) and 3-[(triphenyl- and 3-[(tributylphosphoranylidene)amino]-1,6-methano[10]annulenes (9x,y) were generated by the Staudinger reaction of 2- and 3-azido-1,6-methano[10]annulenes (5 and 6). The compound 8x was inert to alpha,beta-unsaturated ketones, while compounds 8y and 9y were found to react with alpha,beta-unsaturated ketones in enamine-alkylation process followed by aza-Wittig reaction and dehydrogenation to give 7,12- and 5,10-methanocyclodeca[b]pyridines 20a-f and 26a,f, respectively. The reactivity of 8 and 9 as well as the site selectivity of 9 was suggested by their C-13 NMR spectra, in which the carbon signals of the nucleophilic center appear at higher field as compared to those of 1,6-methano[10]annulene. Structural properties of 20a-f and 26a,f were examined by H-1 NMR and UV spectra. The H-1 NMR spectra analyzing aromatic characters clarified both remarkable reduction of a ring current and appearance of bond alternation as compared to the parent 1,6-methano[10]annulene (1). The UV spectra exhibiting a prolonged cyclic conjugation are in contrast to their 10-pi electron analogues, 1,6-methano[10]annulene (1) and quinoline derivatives.

  DOI：

  10.1021/jo00028a040

文献信息

• Neidlein, Richard; Constantinescu, Take; Kohl, Matthias, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 59, # 1-4, p. 165 - 168
  作者：Neidlein, Richard、Constantinescu, Take、Kohl, Matthias

  DOI：——

  日期：——
• Neidlein, Richard; Constantinescu, Take; Boese, Roland, Chemische Berichte, 1988, vol. 121, p. 1699 - 1702
  作者：Neidlein, Richard、Constantinescu, Take、Boese, Roland、Blaeser, Dieter

  DOI：——

  日期：——
• Neidlein, Richard; Constantinescu, Take, Chemische Berichte, 1989, vol. 122, p. 1003 - 1008
  作者：Neidlein, Richard、Constantinescu, Take

  DOI：——

  日期：——
• NEIDLEIN, RICHARD;CONSTANTINESCU, TAKE, CHEM. BER., 122,(1989) N, C. 1003-1007
  作者：NEIDLEIN, RICHARD、CONSTANTINESCU, TAKE

  DOI：——

  日期：——
• NEIDLEIN, RICHARD;KOHL, MATTHIAS, PHOSPH., SULFUR AND SILICON AND RELAT. ELEM., 58-59,(1991) N-4, C. 165-16+
  作者：NEIDLEIN, RICHARD、KOHL, MATTHIAS

  DOI：——

  日期：——