N-(1-phenylvinyl)iminotributylphosphorane | 107170-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-phenylvinyl)iminotributylphosphorane
• 英文别名: tributyl(1-phenylethenylimino)-λ5-phosphane
• CAS: 107170-78-5
• 化学式: C₂₀H₃₄NP
• 分子量: 319.47
• InChiKey: CKDHHHIPXAGCPW-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 0.15 Torr)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(1-phenylvinyl)iminotributylphosphorane 、 反式-1-苯基-2-丁烯-1-酮 以20%的产率得到
  参考文献：
  名称：

  KOBAYASHI TOMOSHIGE; NITTA MAKOTO, CHEM. LETT.,(1986) N 9, 1549-1552

  摘要：

  DOI：
• 作为产物：
  描述：

  三丁基膦 、 1-azidostyrene 以75%的产率得到
  参考文献：
  名称：

  KOBAYASHI, TOMOSHIGE;IINO, YUKIO;NITTA, MAKOTO, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1987) N 7, 1237-1243

  摘要：

  DOI：

文献信息

• A Novel Route to Phenyl-substituted Pyridines by the Reaction of<i>N</i>-(1-Phenylvinyl)iminophosphoranes with α,β-Unsaturated Ketones
  作者：Tomoshige Kobayashi、Makoto Nitta

  DOI：10.1246/cl.1986.1549

  日期：1986.9.5

  The N-(1-phenylvinyl)iminotriphenylphosphorane or N-(1-phenylvinyl)iminotributylphosphorane reacted with α,β-unsaturated ketones to undergo a novel C–C bond formation followed by aza-Wittig reaction to result in the formation of phenyl-substituted pyridines.

  N-(1-苯基乙烯基)亚氨基三苯基正膦或 N-(1-苯基乙烯基)亚氨基三丁基正膦与 α,β-不饱和酮反应形成新的 C-C 键，然后进行氮杂-维蒂希反应，形成苯基取代的吡啶。
• Iino, Yukio; Kobayashi, Tomoshige; Nitta, Makoto, Heterocycles, 1986, vol. 24, # 9, p. 2437 - 2441
  作者：Iino, Yukio、Kobayashi, Tomoshige、Nitta, Makoto

  DOI：——

  日期：——
• On the reaction of (vinylimino)phosphorane and related compounds. 22. Syntheses and structural studies of methanocycloundeca[b]pyrrole ring systems
  作者：Nobuhiro Kanomata、Kenichi Kamae、Yukio Iino、Makoto Nitta

  DOI：10.1021/jo00046a010

  日期：1992.9

  Novel 2-phenyl-6,11- and 2-phenyl-4,9-methanocycloundeca[b]pyrroles (15a and 16a) were synthesized in moderate yields by the reaction of 3,8-methano[11]annulenone (3), a 10pi-electron vinylogue of tropone, with [(l-phenylvinyl)imino]triphenylphosphorane (8a) and subsequent dehydrogenation. Similarly, the reaction of the annulenone 3 with (inden-3-ylimino)tributylphosphorane (8c) and subsequent aromatization afforded 7,12- and 9,14-methano-15H-cycloundeca[b]indeno[2,3-d]pyrroles (15c and 16c), which also have methanocycloundeca[b]pyrrole ring systems. Preparation of 2-phenyl-5,10-methanocycloundeca[b]pyrrole (17), an isomer of both 15a and 16a, was also accomplished in low yield by the reaction of 4,9-methano[ll]annulenone (5) with an excess of [(1-phenylvinyl)imino]tributylphosphorane (8d). The reactivity of annulenone 5 with (vinylimino)phosphoranes was found to be quite low as compared to the higher reactivity of annulenone 3 and tropone. Compounds 15a,c, 16a,c, and 17 are the first nitrogen analogues of cyclopentacycloundecene ring systems which have vinylogous structures of 1-azaazulene. Structures of the products obtained were examined by H-1 NMR spectra and UV spectra. The H-1 NMR spectra clarified that the compounds 15a,c, 16a,c, and 17 are aromatic molecules having a diatropic 14pi-electron system, and 5,10-methano derivative 17 has a more diatropic nature than the compounds 15a,c and 16a,c. The UV spectra of 15a,c, 16a,c, and 17 exhibited increased cyclic conjugation of the aromatic perimeter according to a bathochromic shift of the longest absorption maxima as compared to the corresponding 1-azaazulene derivatives.