7-methoxy-1-methylphenanthrene | 21013-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 7-methoxy-1-methylphenanthrene
• 英文别名: 7-Methoxy-1-methyl-phenanthren；1-Methyl-7-methoxy-phenanthren；7-Methoxy-1-methylphenanthrene
• CAS: 21013-09-2
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: YPBOKLIWCMJZCP-UHFFFAOYSA-N

物化性质

• 熔点：
  133.5-134.5 °C
• 沸点：
  390.7±11.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-methoxy-1-methylphenanthrene 在 吡啶盐酸盐 作用下， 生成 2-hydroxy-8-methylphenanthrene
  参考文献：
  名称：

  Effect of Deinking Paper Sludge Compost On Nutrient Uptake and Yields of Snap Bean And Potatoes Grown in Rotation

  摘要：

  DOI：

  10.1080/1065657x.2001.10702025
• 作为产物：
  描述：

  7-methoxy-1-methyl-3,4-dihydro-phenanthrene-2-carboxylic acid 在 palladium on activated charcoal 、 丙酮 作用下， 生成 7-methoxy-1-methylphenanthrene
  参考文献：
  名称：

  ÜberSteroide。75. Mitteilung。六氢菲二碳二烯。ÜberoestrogeneCarbonsäurenXXII

  摘要：

  DOI：

  10.1002/hlca.19480310142

文献信息

• A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction
  作者：Yue Zhong、Wen-Yu Wu、Shao-Peng Yu、Tian-Yuan Fan、Hai-Tao Yu、Nian-Guang Li、Zhi-Hao Shi、Yu-Ping Tang、Jin-Ao Duan

  DOI：10.3762/bjoc.15.26

  日期：——

  Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C–H activation, decarbonylation and subsequent a retro-Diels–Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products

  在此，我们报告了一种新颖的钯催化反应，该反应使用芳基碘化物、邻溴苯甲酰氯和降冰片二烯在一锅中产生菲衍生物。这一戏剧性的转变经历了邻位C-H 活化、脱羰和随后的逆狄尔斯-阿尔德过程。令人高兴的是，与之前报道的方法相比，该方案具有更宽的底物范围、更短的反应时间和更高的产物产量。
• Palladium-Catalyzed Decarboxylative Annulation Reaction of Aryl Iodides and Methyl 2-Haloarenecarboxylates
  作者：Ying Fu、Xi Chen、Hao Chen、Jia-Jia Liu、Zhengyin Du

  DOI：10.1021/acs.orglett.4c01484

  日期：2024.6.28

  A ligand-free palladium-catalyzed and norbornadiene-mediated annulation reaction of iodoarenes with methyl 2-haloarenecarboxylates is reported. The sequentially accomplished reaction comprises intermolecular C–H arylation, followed by intramolecular decarboxylative annulation, affording various valuable phenanthrenes. This reaction protocol could be expanded to triphenylene syntheses whereby norbornene

  报道了碘芳烃与 2-卤代芳烃甲酸甲酯的无配体钯催化和降冰片二烯介导的环化反应。随后完成的反应包括分子间C-H芳基化，然后是分子内脱羧环化，得到各种有价值的菲。该反应方案可以扩展到苯并菲的合成，其中降冰片烯是助催化剂。有趣的是，甲酯的脱羧是通过溶剂介导的 C Me -O 键断裂完成的。
• ——
  作者：M. Dellagreca、A. Fiorentino、P. Monaco、A. Pollio、L. Previtera、A. Zarrelli

  DOI：10.1023/a:1005463802388

  日期：——

  9,10-Dihydrophenanthrenes and phenanthrenes, mimics of natural compounds with strong antialgal activity, have been synthesized through cross-coupling of 1-(2-iodo-5-methoxy)-phenylethanol with variously substituted iodobenzenes. The synthetic compounds, bearing a hydroxyl or a methoxyl group at C-2 and a methyl in the C ring, were tested against the green alga Selenastrum capricornutum. All compounds, except 2-methoxy-7-methylphenanthrene, caused inhibition of algal growth by more than 70% at 10(-4) M, and many of them retained this strong activity at 10(-5) M.
• 70. Syntheses in the phenanthrene series. Part II. 7-Methoxy-1-methylphenanthrene and a new route to phenanthrene
  作者：W. F. Short、H. Stromberg、A. E. Wiles

  DOI：10.1039/jr9360000319

  日期：——
• Directed Metalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes
  作者：Kåre B. Jørgensen、Toni Rantanen、Thilo Dörfler、Victor Snieckus

  DOI：10.1021/acs.joc.5b01300

  日期：2015.10.2

  A general, efficient, and regioselective synthesis of a series of hydroxylated 1-methylphenanthrenes 9 by a combined directed ortho metalation (DoM)-Suzuki-Miyaura cross-coupling directed remote metalation (DreM) sequence is reported. Diversity to this methodology was achieved by a regioselective DoM rather than DreM reaction, affording more highly substituted phenanthrols (Table 2). Application of the turbo-Grignard reagent (i-PrMgCl-LiCl) in the Ni-catalyzed Corriu-Kumada reaction gave efficient decarbamoylation (Tables 3 and 4). Additional features are the TMS protecting group and halo-induced ipso-desilylation tactics applied to the regioselective synthesis of phenanthrenes (Scheme 2).