methyl -o-toluate | 136391-75-8

• 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: methyl -o-toluate
• 英文别名: methyl [carboxy-13C]-o-toluate
• CAS: 136391-75-8
• 化学式: C₉H₁₀O₂
• 分子量: 151.166
• InChiKey: WVWZECQNFWFVFW-QBZHADDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl -o-toluate 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-methyl[carbonyl-13C]benzaldehyde
  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：

  重氮甲烷 、 -o-toluic acid 以97.5%的产率得到methyl -o-toluate
  参考文献：
  名称：

  Tomioka, Hideo; Kobayashi, Noriyuki; Murata, Shigeru, Journal of the American Chemical Society, 1991, vol. 113, # 23, p. 8771 - 8778

  摘要：

  DOI：

文献信息

• The Elusive Benzocyclobutenylidene:  A Combined Computational and Experimental Attempt
  作者：Athanassios Nicolaides、Takeshi Matsushita、Kohichi Yonezawa、Shinji Sawai、Hideo Tomioka、Louise L. Stracener、Jonathan A. Hodges、Robert J. McMahon

  DOI：10.1021/ja0039482

  日期：2001.3.1

  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.
• Tomioka, Hideo; Kobayashi, Noriyuki; Murata, Shigeru, Journal of the American Chemical Society, 1991, vol. 113, # 23, p. 8771 - 8778
  作者：Tomioka, Hideo、Kobayashi, Noriyuki、Murata, Shigeru、Ohtawa, Yasuki

  DOI：——

  日期：——