α-deuteriosuberene | 137571-37-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: α-deuteriosuberene
• 英文别名: 5-deuteriosuberene；2-Deuteriotricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene
• CAS: 137571-37-0
• 化学式: C₁₅H₁₂
• 分子量: 193.252
• InChiKey: QPJORFLSOJAUNL-WORMITQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5,5-Dideuterio-5H-dibenzocycloheptene 在 水 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以30%的产率得到α-deuteriosuberene
  参考文献：
  名称：

  Excited-state carbon acids. Facile benzylic carbon-hydrogen bond heterolysis of suberene on photolysis in aqueous solution: a photogenerated cyclically conjugated eight .pi. electron carbanion

  摘要：

  The possibility of excited-state carbon acid behavior of the dibenzylic protons of several dibenzannelated systems related to suberene (1) has been investigated in aqueous solution and in several organic solvents. It was found that only suberene (1) displayed observable excited-state carbon acid behavior. Thus photolysis of 1 in D2O-CH3CN solutions resulted in facile exchange of the benzylic protons with deuterium from D2O. Extended photolysis resulted in incorporation of two deuteriums at the benzylic position. Quantum yields for initial deuterium incorporation are in the range 0.02-0.03 for 1 in D2O-CH3CN solutions. Deuterium exchange from the benzylic position with solvent protons was also observed on photolysis of 5,5-dideuterio-5H-dibenzo[a,d]cycloheptene (2), where each deuterium atom was exchanged with solvent H2O in a sequential manner. Fluorescence quenching by water (in CH3CN solution) of the exchanging suberene systems (1 and 2) gave linear Stern-Volmer plots, with k(q) = (1.68 +/- 0.08) x 10(8) M-1 s-1 for 1 and (0.61 +/- 0.06) x 10(8) M-1 s-1 for 2, which corresponds to an isotope effect for quenching by water, (k(H)/k(D))q = 2.8 +/- 0.4. Fluorescence titration of 1 and 11 as a function of medium acidity gave an estimate of pK(S1) = -1 for these carbon acids. This compares to their estimated pK(S0) = 31-38.

  DOI：

  10.1021/jo00029a020

文献信息

• Enhanced formation of 8.pi.(4n) conjugated cyclic carbanions in the excited state: first example of photochemical C-H bond heterolysis in photoexcited suberene
  作者：Peter. Wan、Erik. Krogh、Becky. Chak

  DOI：10.1021/ja00220a076

  日期：1988.6