8-methoxy-6-methylphenanthridine

• 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: 8-methoxy-6-methylphenanthridine
• 英文别名: 2-methoxy-10-methylphenanthrene
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: UTVWSNWNGFOKOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-(4'-methoxyphenyl)benzyl bromide 在 copper(l) iodide 、 [(C₆F₅)₃PAuNTf₂] 、 四丁基碘化铵 、 potassium carbonate 、 双三氟甲烷磺酰亚胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.0h， 生成 8-methoxy-6-methylphenanthridine
  参考文献：
  名称：

  黄金催化的6-Exo-Dig环异构化：一种多功能的官能化菲的方法

  摘要：

  已经开发了一种新型的金催化的邻炔丙基联芳基的6- exo - dig环异构化方法，该方法可以方便地获得官能化的菲，而且收率大体上很高。该方法的显着特征是易于获得的起始原料，温和的反应条件和广泛的底物范围。

  DOI：

  10.1002/asia.201400034

文献信息

• Di-<i>tert</i>Butyl Peroxide-Promoted Sequential Methylation and Intramolecular Aromatization of Isonitriles
  作者：Qiang Dai、Jin-Tao Yu、Xiaomei Feng、Yan Jiang、Haitao Yang、Jiang Cheng

  DOI：10.1002/adsc.201400660

  日期：2014.11.3

  AbstractThe di‐tert butyl peroxide (DTBP)‐promoted sequential reaction of isonitriles is developed, leading to 6‐methylphenanthridine derivatives in moderate to excellent yields. DTBP served as both promoter and methyl source. The procedure proceeds through the addition of a methyl radical derived from the peroxide to the isonitrile followed by aromatic homolytic cyclization. It tolerates a series of functional groups, such as fluoro, chloro, acetyl, methoxycarbonyl, cyano and trifluoromethyl.magnified image
• Oxygenated phenanthrenes via quinol ketals: Cyclization vs. migration
  作者：Gary W. Morrow、Tina M. Marks、Debra L. Sear

  DOI：10.1016/0040-4020(95)00593-w

  日期：1995.9

  2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromostyrenes with quinone monoketals followed by acid-mediated cyclization of the resulting p-arylquinol ketals. Substitution at the bromostyrene side-chain or the quinone monoketal ring had only a modest effect on yields, but oxygen substitution on the bromostyrene aromatic nucleus resulted in a competing 1,2-aryl migration arising during the quinol ketal cyclization step. The extent of this rearrangement was found to be a function of the Lewis acid/solvent system employed.
• Gold-Catalyzed 6-<i>Exo</i>-<i>Dig</i>Cycloisomerization: A Versatile Approach to Functionalized Phenanthrenes
  作者：Chao Shu、Long Li、Cheng-Bin Chen、Hong-Cheng Shen、Long-Wu Ye

  DOI：10.1002/asia.201400034

  日期：2014.6

  A novel gold‐catalyzed 6‐exo‐dig cycloisomerization of o‐propargylbiaryls has been developed that provides ready access to functionalized phenanthrenes in largely good to excellent yields. Notable features of this method are readily available starting materials, mild reaction conditions, and broad substrate scope.

  已经开发了一种新型的金催化的邻炔丙基联芳基的6- exo - dig环异构化方法，该方法可以方便地获得官能化的菲，而且收率大体上很高。该方法的显着特征是易于获得的起始原料，温和的反应条件和广泛的底物范围。