菲-3-甲酸甲酯 | 5345-98-2

• 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: 菲-3-甲酸甲酯
• 中文别名: 3-菲羧酸甲酯
• 英文名称: methyl 3-phenanthrenecarboxylate
• 英文别名: methyl phenanthrenecarboxylate；3-methoxycarbonylphenanthrene；phenanthrene-3-carboxylic acid methyl ester；Phenanthren-3-carbonsaeure-methylester；Phenanthren-carbonsaeure-(3)-methylester；Methyl phenanthrene-3-carboxylate
• CAS: 5345-98-2
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: PFARRVCKSKRETF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  菲-3-甲酸甲酯 在 氢氧化钾 作用下， 以 二乙二醇 为溶剂， 生成 3-菲甲酸
  参考文献：
  名称：

  The Five Monocarboxylic Acids of Phenanthrene^1,2

  摘要：

  DOI：

  10.1021/jo01074a004
• 作为产物：
  描述：

  2-Methoxystilben-4'-carbonsaeuremethylester 在 碘 作用下， 生成 菲-3-甲酸甲酯
  参考文献：
  名称：

  Cresp,T.M. et al., Journal of the Chemical Society. Perkin transactions I, 1974, p. 2435 - 2447

  摘要：

  DOI：

文献信息

• Air-Driven Potassium Iodide-Mediated Oxidative Photocyclization of Stilbene Derivatives
  作者：Tomoya Matsushima、Sayaka Kobayashi、Soichiro Watanabe

  DOI：10.1021/acs.joc.6b01450

  日期：2016.9.2

  A new method has been developed for the potassium iodide-mediated oxidative photocyclization of stilbene derivatives. Compared with conventional iodine-mediated oxidative photocyclization reactions, this new method requires shorter reaction times and affords cyclized products in yields of 45–97%. This reaction proceeds with a catalytic amount of potassium iodide and works in an air-driven manner without

  已开发出一种新方法，用于碘化钾介导的二苯乙烯衍生物的氧化光环化。与传统的碘介导的氧化光环化反应相比，这种新方法需要更短的反应时间，并且环化产物的收率为45–97％。该反应以催化量的碘化钾进行，并且在不添加外部清除剂的情况下以空气驱动的方式进行。还研究了使用TEMPO的二苯乙烯衍生物的自由基介导的氧化光环化反应。
• Reactions of K-region oxides of carcinogenic and noncarcinogenic aromatic hydrocarbons. Comparative studies on reactions with nucleophiles and acid-catalyzed reactions.
  作者：TOSHIHIKO OKAMOTO、KOICHI SHUDO、NAOKI MIYATA、YOSHIYASU KITAHARA、SHUNJI NAGATA

  DOI：10.1248/cpb.26.2014

  日期：——

  Several K-region arene oxides of carcinogenic and noncarcinogenic polycyclic aromatic hydrocarbons were synthesized, and their reactivities with various nucleophiles and their acid-catalyzed reactions were discussed. Relationship between these chemical reactivities and mutagenicity was also discussed.

  合成了几种致癌和非致癌多环芳烃的 K 区芳烃氧化物，并讨论了它们与各种亲核物的反应活性及其酸催化反应。还讨论了这些化学反应性与致突变性之间的关系。
• Structural Effects on Photochemical Cycloaddition of Phenanthrene-and Naphthalenecarboxylic Esters. Enhancement of Reactivity of an Ester Carbonyl Group by Interchromophoric Links.
  作者：Hiroki Itoh、Mahoko Takada、Fumihiro Asano、Yasuhisa Senda、Hirochika Sakuragi、Katsumi Tokumaru

  DOI：10.1246/bcsj.66.224

  日期：——

  On irradiation in benzene, (E)-5-(p-methoxyphenyl)-4-pentenyl 3-, 9-phenanthrenecarboxylate, 1-, and 2-naphthalenecarboxylate gave novel olefinic aldehydes presumably derived from oxetane precursors, the intramolecular carbonyl adducts. Intermolecular carbonyl addition was not detected between the corresponding ester and olefinic chromophores. Enhancement of reactivity of the ester carbonyl group in the linked systems is discussed on the basis of experimental and theoretical studies.

  在苯中辐照时，(E)-5-（对甲氧基苯基）-4-戊烯 3-、9-菲羧酸酯、1-和 2-萘羧酸酯产生了新的烯烃醛，这些烯烃醛可能来自氧杂环丁烷前体，即分子内羰基加合物。在相应的酯和烯烃发色团之间未检测到分子间羰基加成。在实验和理论研究的基础上，讨论了酯羰基在连接体系中反应活性的增强。
• Visible-Light-Mediated Synthesis of Phenanthrenes through Successive Photosensitization and Photoredox by a Single Organocatalyst
  作者：Tanumoy Mandal、Samrat Mallick、Nidhi Kumari、Suman De Sarkar

  DOI：10.1021/acs.orglett.2c03612

  日期：2022.11.18

  An efficient approach for the synthesis of phenanthrene scaffolds by utilizing the dual catalytic activity of an organo-photocatalyst is documented. The controlled cascade transformation proceeds via in situ diazotization followed by olefin isomerization and subsequent arene radical generation through photoreduction. The overall process demonstrates both the photosensitization and photoredox properties

  记录了一种利用有机光催化剂的双重催化活性合成菲支架的有效方法。受控的级联转化通过原位重氮化进行，然后是烯烃异构化，随后通过光还原产生芳烃自由基。整个过程展示了单一有机光催化剂的光敏化和光氧化还原特性，并以高精度和高效性促进了所需的分子内环化。在此背景下，采用了未充分开发的有机催化剂吖啶橙碱，并记录了催化剂与底物之间的光物理相互作用以及详细的反应动力学。
• 1-Phenylisobenzofuran, 1-phenylnaphtho[2,3-c]furan, 1-phenylnaphtho[1,2-c]furan, and 3-phenylnaphtho[1,2-c]furan via cyclic hemiaminal, hemiacetal, and acetal precursors
  作者：James G. Smith、Deryn E. Fogg、Ian J. Munday、Richard E. Sandborn、Peter W. Dibble

  DOI：10.1021/jo00248a009

  日期：1988.6