4b,8d-Dihydro-dibenzo[a,f]cyclopropa[cd]pentalene-8b,8c-dicarboxylic acid 8c-isopropyl ester | 124372-05-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 4b,8d-Dihydro-dibenzo[a,f]cyclopropa[cd]pentalene-8b,8c-dicarboxylic acid 8c-isopropyl ester
• 英文别名: 1-Propan-2-yloxycarbonylpentacyclo[7.7.0.02,16.03,8.010,15]hexadeca-3,5,7,10,12,14-hexaene-2-carboxylic acid；1-propan-2-yloxycarbonylpentacyclo[7.7.0.02,16.03,8.010,15]hexadeca-3,5,7,10,12,14-hexaene-2-carboxylic acid
• CAS: 124372-05-0
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: ROSPVMDEDNYGGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-propyl 12-carboxy-9,10-ethenoanthracene-11-carboxylate 以 various solvent(s) 为溶剂， 以5%的产率得到4b,8d-Dihydro-dibenzo[a,f]cyclopropa[cd]pentalene-8b,8c-dicarboxylic acid 8c-isopropyl ester
  参考文献：
  名称：

  二π-甲烷光重排的质子控制

  摘要：

  二苯并barrelene-11,12-二羧酸（9,10-etheno-9,10-dihydroanthracene-11,12-di羧酸）的单酯（1）的质子化和氢键状态控制其di-π的区域选择性-甲烷光重排。

  DOI：

  10.1039/c39890000600

文献信息

• Prototropic control of organic photochemistry. Hydrogen bonding effects on the di-.pi.-methane photorearrangement
  作者：Miguel A. Garcia-Garibay、John R. Scheffer、Darrel G. Watson

  DOI：10.1021/jo00027a043

  日期：1992.1

  The IR and UV spectra as well as the photochemistry of the isopropyl monoester of dibenzobarrelene dicarboxylic acid 2 were analyzed in detail in several media. A correlation was found between the photochemical results and the spectroscopically detected hydrogen-bonded structures of 2. An equilibrium between dimeric (2-HD) and intramolecularly hydrogen bonded (2-HI) structures was detected by IR spectroscopy in nonpolar solvents having weak hydrogen-bond-accepting capabilities. The ratio of the two regioisomeric dibenzosemibullvalene products 3 and 4 formed in the di-pi-methane photorearrangement of 2 was found to correlate with such an equilibrium, and it was concluded that intramolecular (2-HI) and dimeric (2-HD) hydrogen-bonded structures display significantly different photochemical reactivity. The infrared spectra and the photoproduct ratio in polar solvents possessing hydrogen-bond-accepting capabilities (e.g., acetonitrile), on the other hand, turned out to be concentration independent. High regioselectivity was found in the solid state where the dimer 2-HD is the only species, leading to 4 as the major product. In contrast, 3 was obtained preferentially in aqueous sodium bicarbonate solutions where 2 exists as the carboxylate anion. Supporting evidence regarding the different hydrogen bonding arrangements in 2 was found in the solvent effects on its UV spectra.