Methyl 3-methoxy-9,10-dihydrophenanthrene-2-carboxylate | 85531-82-4

• 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 3-methoxy-9,10-dihydrophenanthrene-2-carboxylate
• 英文别名: 3-methoxy-2-(methoxycarbonyl)-9,10-dihydrophenanthrene
• CAS: 85531-82-4
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: MRJMJQZXOUTPTD-UHFFFAOYSA-N

物化性质

• 沸点：
  429.9±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 3-methoxy-9,10-dihydrophenanthrene-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到(3-Methoxy-9,10-dihydro-phenanthren-2-yl)-methanol
  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：

  1,1-二甲氧基乙烯 、 Methyl 2-oxo-5,6-dihydro-2H-naphtho<1,2-b>pyran-3-carboxylate 以 甲苯 为溶剂， 反应 15.0h， 以78%的产率得到Methyl 3-methoxy-9,10-dihydrophenanthrene-2-carboxylate
  参考文献：
  名称：

  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狄尔斯-阿尔德反应：芳基环化的简单温和方法

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)85651-8

文献信息

• 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
• 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：——