| 937711-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• CAS: 937711-75-6
• 化学式: C₁₁H₇NO
• 分子量: 169.183
• InChiKey: HWQLWVAWBUOAKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  在 水 作用下， 生成 Dioxymethylenchinaldin
  参考文献：
  名称：

  Observable Azacyclobutenone Ylides with Antiaromatic Character from 2-Diazoacetyl-azaaromatics

  摘要：

  Azacyclobutenone ylides 2 and 11 were generated in solution by laser flash photolysis of 2-diazoacetylpyridine (1) and 3-diazoacetylpyridazine (10), respectively, together with the corresponding ketenes. The ylides were identified by their characteristic IR and UV spectra: 2, nu (CH3CN) 1725 cm(-1), lambda(max) 360 and 550 (br) nm; 11, nu (CH3CN) 1776 cm(-1), lambda(max) 370 and 550 (br) nm. 2-Triisopropylsilyldiazoacetylpyridine 20 upon photolysis at 5 degrees C in CH3CN forms the ylide 21 as a rather persistent (T-1/2 2 h at 25 degrees C) purple solution, nu (CH3CN) 1718 cm(-1), lambda(max) 245, 378 and 546 (br) nm, but no ketene is observed. Quinolyl ylide 14 and pyridyl ylides 17 and 19 with Me and 2-pyridyl substituents, respectively, with characteristic IR and UV spectra were also generated. The H-1 NMR spectrum of the pyridyl ring of 21 shows substantial upfield shifts relative to those of 20. Calculated nucleus-independent chemical shifts (NICS) for 2, 11, and 21 are comparable to those for benzocyclobutadiene (22) and benzocyclobutenone enolate (23), with substantial positive values for the 4-membered rings, while the NICS values for the 6-membered rings are significantly more positive than for benzene or pyridine. Significant bond alternation is also found in the calculated ylide structures, and these results suggest strong antiaromatic character for the 4-membered rings of 2, 11, 14, 17, 19, and 21, and greatly reduced aromatic character for the 6-membered rings.

  DOI：

  10.1021/ja0686920
• 作为产物：
  描述：

  喹醛酰氯 以 乙醚 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Observable Azacyclobutenone Ylides with Antiaromatic Character from 2-Diazoacetyl-azaaromatics

  摘要：

  Azacyclobutenone ylides 2 and 11 were generated in solution by laser flash photolysis of 2-diazoacetylpyridine (1) and 3-diazoacetylpyridazine (10), respectively, together with the corresponding ketenes. The ylides were identified by their characteristic IR and UV spectra: 2, nu (CH3CN) 1725 cm(-1), lambda(max) 360 and 550 (br) nm; 11, nu (CH3CN) 1776 cm(-1), lambda(max) 370 and 550 (br) nm. 2-Triisopropylsilyldiazoacetylpyridine 20 upon photolysis at 5 degrees C in CH3CN forms the ylide 21 as a rather persistent (T-1/2 2 h at 25 degrees C) purple solution, nu (CH3CN) 1718 cm(-1), lambda(max) 245, 378 and 546 (br) nm, but no ketene is observed. Quinolyl ylide 14 and pyridyl ylides 17 and 19 with Me and 2-pyridyl substituents, respectively, with characteristic IR and UV spectra were also generated. The H-1 NMR spectrum of the pyridyl ring of 21 shows substantial upfield shifts relative to those of 20. Calculated nucleus-independent chemical shifts (NICS) for 2, 11, and 21 are comparable to those for benzocyclobutadiene (22) and benzocyclobutenone enolate (23), with substantial positive values for the 4-membered rings, while the NICS values for the 6-membered rings are significantly more positive than for benzene or pyridine. Significant bond alternation is also found in the calculated ylide structures, and these results suggest strong antiaromatic character for the 4-membered rings of 2, 11, 14, 17, 19, and 21, and greatly reduced aromatic character for the 6-membered rings.

  DOI：

  10.1021/ja0686920

文献信息

• Observable Azacyclobutenone Ylides with Antiaromatic Character from 2-Diazoacetyl-azaaromatics
  作者：Nanyan Fu、Annette D. Allen、Shinjiro Kobayashi、Pearl A. Sequeira、Muhong Shang、Thomas T. Tidwell、Masaaki Mishima

  DOI：10.1021/ja0686920

  日期：2007.5.1

  Azacyclobutenone ylides 2 and 11 were generated in solution by laser flash photolysis of 2-diazoacetylpyridine (1) and 3-diazoacetylpyridazine (10), respectively, together with the corresponding ketenes. The ylides were identified by their characteristic IR and UV spectra: 2, nu (CH3CN) 1725 cm(-1), lambda(max) 360 and 550 (br) nm; 11, nu (CH3CN) 1776 cm(-1), lambda(max) 370 and 550 (br) nm. 2-Triisopropylsilyldiazoacetylpyridine 20 upon photolysis at 5 degrees C in CH3CN forms the ylide 21 as a rather persistent (T-1/2 2 h at 25 degrees C) purple solution, nu (CH3CN) 1718 cm(-1), lambda(max) 245, 378 and 546 (br) nm, but no ketene is observed. Quinolyl ylide 14 and pyridyl ylides 17 and 19 with Me and 2-pyridyl substituents, respectively, with characteristic IR and UV spectra were also generated. The H-1 NMR spectrum of the pyridyl ring of 21 shows substantial upfield shifts relative to those of 20. Calculated nucleus-independent chemical shifts (NICS) for 2, 11, and 21 are comparable to those for benzocyclobutadiene (22) and benzocyclobutenone enolate (23), with substantial positive values for the 4-membered rings, while the NICS values for the 6-membered rings are significantly more positive than for benzene or pyridine. Significant bond alternation is also found in the calculated ylide structures, and these results suggest strong antiaromatic character for the 4-membered rings of 2, 11, 14, 17, 19, and 21, and greatly reduced aromatic character for the 6-membered rings.