6-methoxy-3,4-dihydro-2H-phenanthren-1-one | 55651-41-7

• 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: 6-methoxy-3,4-dihydro-2H-phenanthren-1-one
• 英文别名: 6-Methoxy-3,4-dihydro-2H-phenanthren-1-on；6-methoxy-3,4-dihydro-1(2H)-phenanthrenone；6-methoxy-3,4-dihydro-2H-phenanthren-1-one
• CAS: 55651-41-7
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: UEMRSXVSTGARED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxy-3,4-dihydro-2H-phenanthren-1-one 在 盐酸 、 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 三溴化硼 、 汞 、 锌 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 6.0h， 生成 5,6,7,8-tetrahydrophenanthrene-3,4-dione
  参考文献：
  名称：

  Compounds from Danshen. Part 4. Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen)

  摘要：

  Twenty one o-quinonoid-type compounds and one coumarin-type compound related to miltirone (1) have been synthesized with the aim to identify the key structural elements involved in miltirone's interaction with the central benzodiazepine receptor. On the basis of their inhibition of [H-3]flunitrazepam binding to bovine cerebral cortex membranes, it is apparent that ring A of miltirone is essential for affinity. Although increasing the size of ring A from six-membered to seven- and eight-membered is well-tolerated, the introduction of polar hydroxyl groups greatly reduces binding affinity. The presence of 1,1-dimethyl groups on ring A is, however, not essential. On the other hand, the isopropyl group on ring C appears to be critical for binding as its removal decreases affinity by more than 30-fold. It can, however, be replaced with a methyl group with minimal reduction in affinity. Finally, linking ring A and B with a -CH2CH2- bridge results in analogue 89, which is 6 times more potent than miltirone at the central benzodiazepine receptor (IC50 = 0.05-mu-M).

  DOI：

  10.1021/jm00109a022
• 作为产物：
  描述：

  2-萘甲醚 在 盐酸 、 二硫化碳 、 三氯化铝 、 氯化亚砜 、 amalgamated zinc 、 乙醚 、 甲苯 作用下， 生成 6-methoxy-3,4-dihydro-2H-phenanthren-1-one
  参考文献：
  名称：

  2-羟基-17-马-酮的合成。

  摘要：

  DOI：

  10.1021/ja01193a014

文献信息

• Hydroxy-morphinane. Mitteilung. Über die Konstitution der Nebenprodukte bei Morphinanringschlüssen
  作者：A. Grüssner、J. Hellerbach、A. Brossi、O. Schnider

  DOI：10.1002/hlca.19560390524

  日期：——

  The structure of the by-products which are formed during the ring closure to morphinans from the corresponding octahydro-iso-quinolines has been elucidated. They are compounds of apomorphine-like structure: 6-methyl- (benzyl- or allyl-)-10-hydroxy-1,2,3,3a,5-6,6a,7,11b, 11c-decahydro-4H-dibenzo-[de, glquinolines] (VII, XV, XVII).

  已经阐明了在闭环过程中由相应的八氢-异喹啉形成吗啡喃的副产物的结构。它们是阿扑吗啡样结构的化合物：6-甲基-（苄基或烯丙基-）-10-羟基-1,2,3,3a，5-6,6a，7,11b，11c-十氢-4H-二苯并-[de，glquinolines]（七，十五，十七）。
• A New Synthetic Approach to Substituted 1(2<i>H</i>)-Phenanthrenones Based on the Ceric Ammonium Nitrate-Promoted Oxidative Addition of 3-Aryl-1-[(trimethylsilyl)oxy]- cyclohexenes to Ethyl Vinyl Ether
  作者：Paolo Lupattelli、Renzo Ruzziconi、Patrizia Scafato、Sergio Alunni、Anna Belli Paolobelli

  DOI：10.1021/jo972233n

  日期：1998.6.1
• The Structure and Configuration of Resin Acids. Podocarpic Acid and Ferruginol
  作者：William P. Campbell、David Todd

  DOI：10.1021/ja01256a054

  日期：1942.4
• 126. Syntheses in the phenanthrene series. Part IX. 6-Methoxy-1-methylphenanthrene
  作者：Harold Plimmer、W. F. Short、Peter Hill

  DOI：10.1039/jr9380000694

  日期：——
• The Synthesis of 1-Hydroxycyclohepta [de] naphthalene¹
  作者：Richard C. Gilmore、W. J. Horton

  DOI：10.1021/ja01158a023

  日期：1950.2