Methyl 2-methoxy-9,10-dihydrophenanthrene-3-carboxylate | 85531-84-6

• 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: Methyl 2-methoxy-9,10-dihydrophenanthrene-3-carboxylate
• 英文别名: 2-methoxy-9,10-dihydro-phenanthrene-3-carboxylic acid methyl ester；2-Methoxy-9,10-dihydro-phenanthren-3-carbonsaeure-methylester
• CAS: 85531-84-6
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: SJJMXMAHAHFXRD-UHFFFAOYSA-N

物化性质

• 沸点：
  427.8±40.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-methoxy-9,10-dihydrophenanthrene-3-carboxylate 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 3-(bromomethyl)-2-methoxy-9,10-dihydrophenanthrene
  参考文献：
  名称：

  Antimicrobial and antitumor properties of 9,10-dihydrophenanthrenes: structure activity studies on juncusol

  摘要：

  The antimicrobial and cytotoxic properties of a series of 9,10-dihydrophenanthrenes structurally related to juncusol (1a), a postulated phytoalexin with confirmed cytotoxic properties, are detailed. Two simple 9,10-dihydrophenanthrenes, 2,7-dihydroxy-3,8-dimethyl-9,10-dihydrophenanthrene (2h, desvinyljuncusol) and 2-hydroxy-3-methyl-9,10-dihydrophenanthrene (3h), were found to possess in vitro antimicrobial activity comparable with that of the natural product. Two 9,10-dihydrophenanthrenes substituted with quaternary ammonium salts, 2d and 3d, each containing a reactive benzylic dimethyl[(phenylthio)methyl]ammonio group, were found to be 10-20 times more potent than juncusol (1a). Confirmed in vitro cytotoxic activity that parallels antimicrobial activity was found for juncusol (1a), desvinyljuncusol (2h), 2-hydroxy-3-methyl-9,10-dihydrophenanthrene (3h), and the quaternary dimethyl[(phenylthio)methyl]ammonium salts 2d and 3d in a human lymphoblastic leukemia cell culture (CCRF-CEM, IC50 = nt, 9.3, nt, 0.9 and 1.4 microgram/mL, respectively), B-16 mouse melanoma cell culture (IC50 = 12.5, 17.5, 27.7, 0.3, and 0.5 microgram/mL, respectively), and L-1210 mouse lymphocytic leukemia cell culture (IC50 = 13.8, 10.2, 24.5, 1.3, and 3.7 micrograms/mL, respectively). The comparable potency and spectrum of activity of juncusol (1a), desvinyljuncusol (2h), and 2-hydroxy-3-methyl-9,10-dihydrophenanthrene (3h) suggest that the agents are acting as simple phenols in exerting their antimicrobial and cytotoxic effects.

  DOI：

  10.1021/jm00148a031
• 作为产物：
  描述：

  重氮甲烷 、 2-methoxy-9,10-dihydro-phenanthrene-3-carboxylic acid 在 乙醚 作用下， 生成 Methyl 2-methoxy-9,10-dihydrophenanthrene-3-carboxylate
  参考文献：
  名称：

  Texture analysis of IKONOS panchromatic data for Douglas-fir forest age class separability in British Columbia

  摘要：

  This Letter presents the results of textural separability tests obtained by first- and second-order texture methods on different aged Douglas-fir stands in IKONOS panchromatic imagery acquired 3 June 2000 over the Sooke River watershed in British Columbia. The effects of different measures and window sizes on the textural separability are discussed. Small windows sizes were not as effective in separating stands as larger windows sizes. Second-order (spatial co-occurrence homogeneity) texture values were the most effective in distinguishing between age classes. A first-order (variance) texture measure, though still useful, provided less separability.

  DOI：

  10.1080/01431160120769

文献信息

• Inverse electron demand diels-alder reaction of 3-carbomethoxy-2-pyrones with 1,1-dimethoxyethylene: a simple and mild method of aryl annulation
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1016/s0040-4039(00)85651-8

  日期：1982.1

  A simple process for aryl annulation based on the inverse electron demand Diels-Alder reaction of 5,6-substituted-3-carbomethoxy-2-pyrones with 1,1-dimethoxyethylene is described.

  描述了基于5,6-取代的-3-羰基甲氧基-2-吡喃酮与1,1-二甲氧基乙烯的电子反需求Diels-Alder反应的芳基环化的简单方法。
• Inverse electron demand Diels-Alder reactions of 3-carbomethoxy-2-pyrones. Controlled introduction of oxygenated aromatics: benzene, phenol, catechol, resorcinol, and pyrogallol annulation. Regiospecific total synthesis of sendaverine and a preparation of 6,7-benzomorphans
  作者：Dale L. Boger、Michael D. Mullican

  DOI：10.1021/jo00195a033

  日期：1984.10
• Studies in the Phenanthrene Series. XXIII. Synthesis of Acyl Compounds Derived from 2-Hydroxy-9,10-dihydrophenanthrene
  作者：Erich. Mosettig、Alfred H. Stuart

  DOI：10.1021/ja01870a001

  日期：1939.1
• BOGER, D. L.;MULLICAN, M. D., TETRAHEDRON LETT., 1982, 23, N 44, 4551-4554
  作者：BOGER, D. L.、MULLICAN, M. D.

  DOI：——

  日期：——
• Texture analysis of IKONOS panchromatic data for Douglas-fir forest age class separability in British Columbia
  作者：S. E. Franklin、M. A. Wulder、G. R. Gerylo

  DOI：10.1080/01431160120769

  日期：2001.1

  This Letter presents the results of textural separability tests obtained by first- and second-order texture methods on different aged Douglas-fir stands in IKONOS panchromatic imagery acquired 3 June 2000 over the Sooke River watershed in British Columbia. The effects of different measures and window sizes on the textural separability are discussed. Small windows sizes were not as effective in separating stands as larger windows sizes. Second-order (spatial co-occurrence homogeneity) texture values were the most effective in distinguishing between age classes. A first-order (variance) texture measure, though still useful, provided less separability.