[1-13C] 1-(2'-methylphenyl)-2,2,4-trimethylpenta-1,3-dione | 339222-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [1-13C] 1-(2'-methylphenyl)-2,2,4-trimethylpenta-1,3-dione
• CAS: 339222-06-9
• 化学式: C₁₅H₂₀O₂
• 分子量: 233.312
• InChiKey: JWAZNQVLFGNOMX-UJKGMGNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [1-13C] 1-(2'-methylphenyl)-2,2,4-trimethylpenta-1,3-dione 以 正己烷 为溶剂， 以54%的产率得到2-([1'-13C]-1'-hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-2,4-dimethylpentan-3-one
  参考文献：
  名称：

  The Elusive Benzocyclobutenylidene:  A Combined Computational and Experimental Attempt

  摘要：

  Ab initio and density functional theory calculations predict that benzocyclobutenylidene (1) has a singlet ground state in contrast to the parent phenylcarbene and many other simply substituted arylcarbenes. Calculations also predict that 1 should lie in a relatively deep potential well, while its tripler state is 14.5 kcal mol(-1) higher in energy. However,:attempts to observe 1 directly by photolysis of two different nitrogenous precursors were not successful. Irradiation of diazobenzocyclobutene (7) (lambda > 534 nm or lambda > 300 nm) or azibenzocycllobutene (10) (lambda > 328 nm) in Ar matrixes at 10 K leads to the formation of the strained cycloalkyne 7-methylenecyclohepta-3,5-dien-1-yne (3). C-13-Labeled 3 was also prepared in a similar manner. There is very good agreement between experimental IR spectra and computationally derived harmonic vibrational frequencies for 3 and [C-13]-3 and excellent agreement between observed and calculated isotopic shifts. Prolonged short-wavelength irradiation converts 3 into benzocyclobutadiene (5). Phenylacetylene (6) and benzocyclo- butadiene dimer (11) were identified as products arising from flash vacuum pyrolysis of diazirine 10 at 500 degreesC.

  DOI：

  10.1021/ja0039482
• 作为产物：
  描述：

  [1-13C] 1-(2'-methylphenyl)-2,2,4-trimethylpentan-3-on-1-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 以67%的产率得到[1-13C] 1-(2'-methylphenyl)-2,2,4-trimethylpenta-1,3-dione
  参考文献：
  名称：

  The Elusive Benzocyclobutenylidene:  A Combined Computational and Experimental Attempt

  摘要：

  Ab initio and density functional theory calculations predict that benzocyclobutenylidene (1) has a singlet ground state in contrast to the parent phenylcarbene and many other simply substituted arylcarbenes. Calculations also predict that 1 should lie in a relatively deep potential well, while its tripler state is 14.5 kcal mol(-1) higher in energy. However,:attempts to observe 1 directly by photolysis of two different nitrogenous precursors were not successful. Irradiation of diazobenzocyclobutene (7) (lambda > 534 nm or lambda > 300 nm) or azibenzocycllobutene (10) (lambda > 328 nm) in Ar matrixes at 10 K leads to the formation of the strained cycloalkyne 7-methylenecyclohepta-3,5-dien-1-yne (3). C-13-Labeled 3 was also prepared in a similar manner. There is very good agreement between experimental IR spectra and computationally derived harmonic vibrational frequencies for 3 and [C-13]-3 and excellent agreement between observed and calculated isotopic shifts. Prolonged short-wavelength irradiation converts 3 into benzocyclobutadiene (5). Phenylacetylene (6) and benzocyclo- butadiene dimer (11) were identified as products arising from flash vacuum pyrolysis of diazirine 10 at 500 degreesC.

  DOI：

  10.1021/ja0039482