9,10-二氢菲-9-羧酸 | 2222-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 9,10-二氢菲-9-羧酸
• 英文名称: 9,10-Dihydro-phenanthren-9-carbonsaeure
• 英文别名: 9,10-dihydrophenanthrene-9-carboxylic acid
• CAS: 2222-30-2
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: MOXWGTRDIRKZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,10-二氢菲-9-羧酸 在 氯化亚砜 、 氨 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.0h， 生成 9,10-dihydrophenanthrene-9-carboxamide
  参考文献：
  名称：

  Geometry−Affinity Relationships of the Selective Serotonin Receptor Ligand 9-(Aminomethyl)-9,10-dihydroanthracene

  摘要：

  With the exception of its two aromatic rings and basic nitrogen atom, 9-(aminomethyl)-9,10-dihydroanthracene (AMDA; 1) is remarkably devoid of the pharmacophore features usually associated with high-affinity receptor ligands such as the heteroatom hydrogen bonding features of the endogenous ligand serotonin. AMDA does contain a phenylethylamine skeleton within a tricyclic ring system, and the presence of the second aromatic group is necessary for optimal receptor affinity. The structural requirements for the binding of AMDA at 5-HT2A receptors were investigated with respect to the geometric relationship between the two aromatic rings. It appears that the geometry of the AMDA parent is in the optimal range for fold angle between aromatic moieties. Evaluation of conformationally constrained derivatives of AMDA suggests that a chain extended trans, gauche form is most likely responsible for high affinity.

  DOI：

  10.1021/jm010354g
• 作为产物：
  描述：

  9-腈菲 在 sodium hydroxide 、 N,N-二甲基苯胺 作用下， 以 二甲基亚砜 、 二乙二醇 为溶剂， 反应 11.0h， 生成 9,10-二氢菲-9-羧酸
  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

• Photocarboxylation of Benzylic C–H Bonds
  作者：Qing-Yuan Meng、Tobias E. Schirmer、Anna Lucia Berger、Karsten Donabauer、Burkhard König

  DOI：10.1021/jacs.9b05360

  日期：2019.7.24

  the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(1-phenylethyl)benzonitrile generated in situ. The resulting benzylic carbanion reacts with CO2 to generate the corresponding carboxylic acid after protonation. The reaction proceeded without the addition of any sacrificial electron donor, electron acceptor

  sp3 杂化的 C-H 键与 CO2 的羧化是一个具有挑战性的转变。在此，我们报告了在无金属条件下，可见光介导的苄基 C-H 键与 CO2 羧化成 2-芳基丙酸。使用光氧化的三异丙基硅烷硫醇作为氢原子转移催化剂，得到苄基自由基，该自由基接受来自 2,3,4,6-四（9H-咔唑-9-基）-5-（1-苯乙基)苯甲腈原位生成。所得的苄基碳负离子与 CO2 反应，质子化后生成相应的羧酸。反应在不添加任何牺牲电子供体、电子受体或化学计量添加剂的情况下进行。在广泛的底物范围内获得了中等至良好的所需产物产率。
• Kirchner, Nachrichten von der Gesellschaft der Wissenschaften zu Goettingen, Mathematisch-Physikalische Klasse, 1921, p. 159
  作者：Kirchner

  DOI：——

  日期：——
• Pschorr, Chemische Berichte, 1896, vol. 29, p. 500
  作者：Pschorr

  DOI：——

  日期：——
• Reductive photocarboxylation of aromatic hydrocarbons
  作者：Shigeo Tazuke、Shingo Kazama、Noboru Kitamura

  DOI：10.1021/jo00374a011

  日期：1986.11
• Kirchner, Nachrichten von der Gesellschaft der Wissenschaften zu Goettingen, Mathematisch-Physikalische Klasse, 1921, p. 158,159
  作者：Kirchner

  DOI：——

  日期：——