(4-methoxyphenyl)(phenanthren-9-yl)methanol | 796874-03-8

• 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: (4-methoxyphenyl)(phenanthren-9-yl)methanol
• 英文别名: (4-methoxyphenyl)phenanthren-9-ylmethanol；(4-Methoxyphenyl)-phenanthren-9-ylmethanol
• CAS: 796874-03-8
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: YMWPWCXAEYYHDU-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  540.2±38.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)(phenanthren-9-yl)methanol 在 三氯化铝 、 四氯化锡 、 potassium carbonate 作用下， 以 丙酮 、 正戊烷 、 苯 为溶剂， 反应 8.0h， 生成 (2-{2-[(4-methoxyphenyl)phenanthren-9-ylmethyl]phenoxy}ethyl)dimethylamine
  参考文献：
  名称：

  Diaryloxy methano phenanthrenes: a new class of antituberculosis agents

  摘要：

  A new series of diaryloxy methano phenanthrenes were prepared through tertiary-aminoalkylations of [(methoxy-phenyl)-phenanthren-9-yl-methyl]-phenols obtained from Friedel-Crafts alkylations on (methoxy-phenyl)-phenanthren-9-yl-methanols. These series of compounds were evaluated against Mycobacterium tuberculosis H37Rv and showed the desired activity in the range of 6.25 mug/mL in vitro. One of the compound 12j protects the mice from the challenge of M. tuberculosis in vivo, as 30% of the mice were survived at treatment of 50mg/kg body weight. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.058
• 作为产物：
  描述：

  9-溴菲 、 4-甲氧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以78%的产率得到(4-methoxyphenyl)(phenanthren-9-yl)methanol
  参考文献：
  名称：

  Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

  摘要：

  通过一种简便且模块化的方法，成功地合成了三芳基甲烷，收率良好，该方法包括两步反应序列，最后一步是使用铜(II)催化的芳基硼酸酯与二芳基甲醇进行芳基化反应。通过使用这种方法，合成了各种对称和非对称的三芳基甲烷化合物。作为新开发方法的应用，我们展示了一种高产率的合成方法，用于合成三芳基甲烷中间体，以制备一种抗乳腺癌药物候选化合物。

  DOI：

  10.3762/bjoc.12.49

文献信息

• Effect of substituents on diarylmethanes for antitubercular activity
  作者：Gautam Panda、Maloy Kumar Parai、Sajal Kumar Das、Shagufta、Manish Sinha、Vinita Chaturvedi、Anil K. Srivastava、Y.S. Manju、Anil N. Gaikwad、Sudhir Sinha

  DOI：10.1016/j.ejmech.2006.09.020

  日期：2007.3

  Aminoalkyl derivatives of diarylmethanes were prepared using Grignard, Friedel-Crafts arylation and aminohydrochloride chain formation reactions. These series of compounds were evaluated against Mycobacterium tuberculosis H(37)R(v) and showed the activity in the range of 6.25-25 microg/mL. Effect of heteroaryl, anthracenyl and phenanthrene groups on diarylmethane pharmacophores for antitubercular activity

  使用格利雅（Grignard），弗瑞德-克来福特（Friedel-Crafts）芳基化反应和氨基盐酸盐链形成反应来制备二芳基甲烷的氨基烷基衍生物。对结核分枝杆菌H（37）R（v）评估了这一系列化合物，其活性范围为6.25-25 microg / mL。描述了杂芳基，蒽基和菲基团对二芳基甲烷药效团抗结核活性的影响。
• Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes
  作者：H Surya Prakash Rao、A Veera Bhadra Rao

  DOI：10.3762/bjoc.12.49

  日期：——

  A facile and modular synthesis of triarylmethanes was achieved in good yield via a two-step sequence in which the final step is the copper(II)-catalyzed arylation of diarylmethanols with arylboronic acids. By using this protocol a variety of symmetrical and unsymmetrical triarylmethanes were synthesized. As an application of the newly developed methodology, we demonstrate a high-yielding synthesis of the triarylmethane intermediate towards an anti-breast-cancer drug candidate.

  通过一种简便且模块化的方法，成功地合成了三芳基甲烷，收率良好，该方法包括两步反应序列，最后一步是使用铜(II)催化的芳基硼酸酯与二芳基甲醇进行芳基化反应。通过使用这种方法，合成了各种对称和非对称的三芳基甲烷化合物。作为新开发方法的应用，我们展示了一种高产率的合成方法，用于合成三芳基甲烷中间体，以制备一种抗乳腺癌药物候选化合物。
• Diaryloxy methano phenanthrenes: a new class of antituberculosis agents
  作者：Gautam Panda、Shagufta、Jitendra Kumar Mishra、Vinita Chaturvedi、Anil K. Srivastava、Ranjana Srivastava、Brahm S. Srivastava

  DOI：10.1016/j.bmc.2004.07.058

  日期：2004.10

  A new series of diaryloxy methano phenanthrenes were prepared through tertiary-aminoalkylations of [(methoxy-phenyl)-phenanthren-9-yl-methyl]-phenols obtained from Friedel-Crafts alkylations on (methoxy-phenyl)-phenanthren-9-yl-methanols. These series of compounds were evaluated against Mycobacterium tuberculosis H37Rv and showed the desired activity in the range of 6.25 mug/mL in vitro. One of the compound 12j protects the mice from the challenge of M. tuberculosis in vivo, as 30% of the mice were survived at treatment of 50mg/kg body weight. (C) 2004 Elsevier Ltd. All rights reserved.