10--9,10-dihydrophenanthrene-9-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 10--9,10-dihydrophenanthrene-9-carboxylic acid methyl ester
• 英文别名: Methyl 10-[4-(dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylate
• 化学式: C₂₄H₂₃NO₂
• 分子量: 357.452
• InChiKey: RYQUDCSGEUNDTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10--9,10-dihydrophenanthrene-9-carboxylic acid methyl ester 在 lithium thiopropiolate 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 2.0h， 生成 10--9,10-dihydrophenanthrene-9-carboxylic acid
  参考文献：
  名称：

  Reductive Photocarboxylation of Phenanthrene:  A Mechanistic Investigation

  摘要：

  Irradiation of a solution of phenanthrene (PHN) in DMSO saturated with CO2 in the presence of N,N-dimethylaniline (DMA) produced 9,10-dihydrophenanthrene-9-carboxylic acid(1) in 55% yield, trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid (2) in 11% yield, a trace of phenanthrene-9-carboxylic acid (3), and a trace of 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5), Addition of cumene, a hydrogen donor, or water, a proton donor, decreased the yield of 2, while addition of certain salts increased its yield, 9-Carboxy-9,10-dihydrophenanthr-10-yl, generated by irradiation of phenanthrene-9-carboxylic acid in the presence of DMA, is proposed to be an intermediate in the formation of the acids,,The quantum yield for the formation of 2 increased to a maximum of 0.13 with increasing light intensity. High CO2 concentrations in DMSO changed the reaction pathway, greatly reducing the yields of 1 and 2, and phenanthrene-9-carboxylic acid (3) and 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5) were formed instead. On the basis of these results reduction of 9-carboxy-9,10-dihydrophenanthr-10-yl with the phenanthrene radical anion is proposed to be a step in the mechanism accounting for trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid formation, Transient spectroscopic evidence in support of this proposal is presented.

  DOI：

  10.1021/jo951702n
• 作为产物：
  描述：

  9-腈菲 在 sodium hydroxide 作用下， 以 乙腈 、 二乙二醇 为溶剂， 反应 8.0h， 生成 10--9,10-dihydrophenanthrene-9-carboxylic acid methyl ester
  参考文献：
  名称：

  Reductive Photocarboxylation of Phenanthrene:  A Mechanistic Investigation

  摘要：

  Irradiation of a solution of phenanthrene (PHN) in DMSO saturated with CO2 in the presence of N,N-dimethylaniline (DMA) produced 9,10-dihydrophenanthrene-9-carboxylic acid(1) in 55% yield, trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid (2) in 11% yield, a trace of phenanthrene-9-carboxylic acid (3), and a trace of 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5), Addition of cumene, a hydrogen donor, or water, a proton donor, decreased the yield of 2, while addition of certain salts increased its yield, 9-Carboxy-9,10-dihydrophenanthr-10-yl, generated by irradiation of phenanthrene-9-carboxylic acid in the presence of DMA, is proposed to be an intermediate in the formation of the acids,,The quantum yield for the formation of 2 increased to a maximum of 0.13 with increasing light intensity. High CO2 concentrations in DMSO changed the reaction pathway, greatly reducing the yields of 1 and 2, and phenanthrene-9-carboxylic acid (3) and 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5) were formed instead. On the basis of these results reduction of 9-carboxy-9,10-dihydrophenanthr-10-yl with the phenanthrene radical anion is proposed to be a step in the mechanism accounting for trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid formation, Transient spectroscopic evidence in support of this proposal is presented.

  DOI：

  10.1021/jo951702n

文献信息

• Reductive Photocarboxylation of Phenanthrene:  A Mechanistic Investigation
  作者：Alexander V. Nikolaitchik、Michael A. J. Rodgers、Douglas C. Neckers

  DOI：10.1021/jo951702n

  日期：1996.1.1

  Irradiation of a solution of phenanthrene (PHN) in DMSO saturated with CO2 in the presence of N,N-dimethylaniline (DMA) produced 9,10-dihydrophenanthrene-9-carboxylic acid(1) in 55% yield, trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid (2) in 11% yield, a trace of phenanthrene-9-carboxylic acid (3), and a trace of 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5), Addition of cumene, a hydrogen donor, or water, a proton donor, decreased the yield of 2, while addition of certain salts increased its yield, 9-Carboxy-9,10-dihydrophenanthr-10-yl, generated by irradiation of phenanthrene-9-carboxylic acid in the presence of DMA, is proposed to be an intermediate in the formation of the acids,,The quantum yield for the formation of 2 increased to a maximum of 0.13 with increasing light intensity. High CO2 concentrations in DMSO changed the reaction pathway, greatly reducing the yields of 1 and 2, and phenanthrene-9-carboxylic acid (3) and 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5) were formed instead. On the basis of these results reduction of 9-carboxy-9,10-dihydrophenanthr-10-yl with the phenanthrene radical anion is proposed to be a step in the mechanism accounting for trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid formation, Transient spectroscopic evidence in support of this proposal is presented.