2-propyl 12-carboxy-9,10-ethenoanthracene-11-carboxylate | 114501-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-propyl 12-carboxy-9,10-ethenoanthracene-11-carboxylate
• 英文别名: 2-Propyl 12-carboxy-9,10-dihydro-9,10-ethenoanthracene-11-carboxylate；16-propan-2-yloxycarbonyltetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene-15-carboxylic acid
• CAS: 114501-55-2
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: KYEFUMYLJWHQJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-propyl 12-carboxy-9,10-ethenoanthracene-11-carboxylate 以 乙腈 为溶剂， 生成 2-Propan-2-yloxycarbonylpentacyclo[7.7.0.02,16.03,8.010,15]hexadeca-3,5,7,10,12,14-hexaene-1-carboxylic acid
  参考文献：
  名称：

  通过在手性空间群中结晶的外消旋混合物的固相反应，产生光学活性

  摘要：

  由于仲丁基基团的无序性，光反应性异丙基/（R，S）-仲丁基二酯3能够在手性空间基团P2 1 2 1 2 1中结晶为外消旋固溶体。辐照此材料的单晶会产生高光学纯度（ee为80％）的产品。伴随的动力学拆分过程使回收的起始原料富含其一种对映异构体。

  DOI：

  10.1016/s0040-4039(00)96626-7
• 作为产物：
  描述：

  9,10-二氢-9,10-乙烯桥蒽-11,12-二甲酸酐 、 异丙醇 生成 2-propyl 12-carboxy-9,10-ethenoanthracene-11-carboxylate
  参考文献：
  名称：

  通过在手性空间群中结晶的外消旋混合物的固相反应，产生光学活性

  摘要：

  由于仲丁基基团的无序性，光反应性异丙基/（R，S）-仲丁基二酯3能够在手性空间基团P2 1 2 1 2 1中结晶为外消旋固溶体。辐照此材料的单晶会产生高光学纯度（ee为80％）的产品。伴随的动力学拆分过程使回收的起始原料富含其一种对映异构体。

  DOI：

  10.1016/s0040-4039(00)96626-7

文献信息

• Prototropic control of the di-π-methane photorearrangement
  作者：Miguel Garcia-Garibay、John R. Scheffer、Darrell G. Watson

  DOI：10.1039/c39890000600

  日期：——

  state of protonation and hydrogen bonding in a monoester (1) of dibenzobarrelene-11,12-dicarboxylic acid (9,10-etheno-9,10-dihydroanthracene-11,12-dicarboxylic acid) controls the regioselectivity of its di-π-methane photorearrangement.

  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。
• Generation of optical activity through solid state reaction of a racemic mixture that crystallizes in a chiral space group
  作者：Miguel Garcia-Garibay、John R. Scheffer、James Trotter、Fred Wireko

  DOI：10.1016/s0040-4039(00)96626-7

  日期：1987.1

  Because of disorder in the sec-butyl group, the photoreactive isopropyl/(R,S)-sec-butyl diester 3 is able to crystallize as a racemic solid solution in the chiral space group P212121. Irradiation of single crystals of this material leads to products of high optical purity (80% ee). An accompanying process of kinetic resolution leaves the recovered starting material enriched in one of its enantiomers

  由于仲丁基基团的无序性，光反应性异丙基/（R，S）-仲丁基二酯3能够在手性空间基团P2 1 2 1 2 1中结晶为外消旋固溶体。辐照此材料的单晶会产生高光学纯度（ee为80％）的产品。伴随的动力学拆分过程使回收的起始原料富含其一种对映异构体。
• 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.