(9S,10S)-9,10-二氢菲-9,10-二甲酸 | 2510-70-5

• 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: (9S,10S)-9,10-二氢菲-9,10-二甲酸
• 英文名称: (9S,10S)-9,10-dihydrophenanthrene-9,10-dicarboxylic acid
• 英文别名: trans-9,10-Dihydrophenanthrene-9,10-dicarboxylic acid
• CAS: 2510-70-5
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: GRRHJJGUXVAZHZ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9S,10S)-9,10-二氢菲-9,10-二甲酸 生成 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The Addition of Alkali Metals to Phenanthrene

  摘要：

  DOI：

  10.1021/ja01291a041
• 作为产物：
  描述：

  菲 在 乙二醇二甲醚 、 sodium 作用下， 生成 (9S,10S)-9,10-二氢菲-9,10-二甲酸
  参考文献：
  名称：

  The Addition of Alkali Metals to Phenanthrene

  摘要：

  DOI：

  10.1021/ja01291a041

文献信息

• Circular Dichroism of 9,10-Dihydrophenanthrene Derivatives Reveals both the Absolute Configuration and Conformation: A Novel Approach to Mislow's Helicity Rule
  作者：Jacek Gawroński、Piotr Grycz、Marcin Kwit、Urszula Rychlewska

  DOI：10.1002/1521-3765(20020916)8:18<4210::aid-chem4210>3.0.co;2-7

  日期：2002.9.16

  The absolute configuration and the conformation of 9,10-trans-disubstituted 9,10-dihydrophenanthrenes, known chiral metabolites of phenanthrene-9,10-oxide, have been determined by circular dichroism. The absolute configuration assignment is based on the sign of the long-wavelength Cotton effect (A-band), which is conformation invariant and originates from benzylic chirality. This provides a new interpretation

  通过圆二色性测定了9，10-反式-二取代的9，10-二氢菲，即菲-9，10-氧化物的手性代谢物的绝对构型和构象。绝对构型分配是基于长波长棉花效应（A波段）的符号，该符号是构象不变的，且起源于苄基手性。这为9,10-二氢菲生色团的情况提供了米索联苯螺旋速率规则的新解释。B带棉花效应的迹象反映了联苯发色团在9,10-二氢菲中的构象。结果表明9,10-二氢菲的手性性质的起源与5,6-反式-二取代的1,3-环己二烯的手性性质密切相关。
• 1063. Studies in photochemistry. Part I. The stilbenes
  作者：M. V. Sargent、C. J. Timmons

  DOI：10.1039/jr9640005544

  日期：——
• 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.