1-fluoro-7-methoxynaphthalen-2-ol | 1447449-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-fluoro-7-methoxynaphthalen-2-ol
• 英文别名: 1-Fluoro-7-methoxynaphthalen-2-OL
• CAS: 1447449-99-1
• 化学式: C₁₁H₉FO₂
• 分子量: 192.19
• InChiKey: ACNFOLBDPQVWJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• 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：
  3

反应信息

• 作为反应物：
  描述：

  1-fluoro-7-methoxynaphthalen-2-ol 在 吡啶 、 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 27.25h， 生成 8-fluoro-7-(pyridin-3-yl)naphthalen-2-ol
  参考文献：
  名称：

  Highly Potent and Selective Nonsteroidal Dual Inhibitors of CYP17/CYP11B2 for the Treatment of Prostate Cancer To Reduce Risks of Cardiovascular Diseases

  摘要：

  Dual CYP17/CYP11B2 inhibitors are proposed as a novel strategy for the treatment of prostate cancer to reduce risks of cardiovascular diseases. Via a combination of ligand- and structure-based approaches, a series of dual inhibitors were designed leading to the 2-(3-pyridyl)naphthalenes 10 and 11 with strong inhibition of both enzymes (IC50 values around 20 nM) and excellent selectivities over CYP11B1, CYP19, and CYP3A4. These compounds are considered as promising candidates for further in vivo evaluation.

  DOI：

  10.1021/jm400484p
• 作为产物：
  描述：

  2-hydroxy-7-methoxy-1-naphthoic acid 在 碳酸氢钠 、 Selectfluor 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到1-fluoro-7-methoxynaphthalen-2-ol
  参考文献：
  名称：

  邻羟基和氨基促进的芳基羧酸的脱羧氟化

  摘要：

  已开发出一种新的脱羧氟化方法，用于从水杨酸类似物合成邻羟基/氨基芳基氟化物，其中邻羟基/氨基在转化中起着重要作用。另外，在温和的条件下以良好至优异的产率获得了各种芳基氟化物。

  DOI：

  10.1002/cjoc.201800016

文献信息

• Transition metal-free dearomatization of halonaphthols with C(sp3)-electrophiles
  作者：Naichen Zhang、Yuanzhi Ye、Lu Bai、Jingjing Liu、Han Wang、Xinjun Luan

  DOI：10.1016/j.cclet.2021.10.037

  日期：2022.5

  halonaphthols with benzyl/allyl bromides is described. Halonaphthols are used as carbon-nucleophiles in dearomatization to form three-dimensional cyclic enones with excellent chemoselectivity, in which etherification of phenolic hydroxyl group could be restrained well by using cesium carbonate as the base. A wide range of cyclic enones is directly prepared from various substituted benzyl/allyl bromides and halonaphthols

  描述了卤代萘酚与苄基/烯丙基溴的第一次分子间亲电脱芳构化。卤代萘酚作为碳亲核试剂在脱芳构化中形成具有优异化学选择性的三维环状烯酮，其中以碳酸铯为碱可以很好地抑制酚羟基的醚化。从各种取代的苄基/烯丙基溴和卤代萘酚直接制备出范围广泛的环状烯酮。机理研究表明直接的 S N 2 反应途径。
• Decarboxylative Fluorination of Arylcarboxylic Acids Promoted by <i>ortho</i> -Hydroxy and Amino Groups
  作者：Dinghai Wang、Zheliang Yuan、Qilun Liu、Pinhong Chen、Guosheng Liu

  DOI：10.1002/cjoc.201800016

  日期：2018.6

  A novel decarboxylative fluorination process has been developed for the synthesis of ortho‐hydroxy/amino arylfluorides from salicylic acid analogs, in which the ortho‐hydroxy/amino group plays an important role in the transformation. In addition, various arylfluorides are obtained in good to excellent yields under mild conditions.

  已开发出一种新的脱羧氟化方法，用于从水杨酸类似物合成邻羟基/氨基芳基氟化物，其中邻羟基/氨基在转化中起着重要作用。另外，在温和的条件下以良好至优异的产率获得了各种芳基氟化物。
• Highly Potent and Selective Nonsteroidal Dual Inhibitors of CYP17/CYP11B2 for the Treatment of Prostate Cancer To Reduce Risks of Cardiovascular Diseases
  作者：Mariano A. E. Pinto-Bazurco Mendieta、Qingzhong Hu、Matthias Engel、Rolf W. Hartmann

  DOI：10.1021/jm400484p

  日期：2013.8.8

  Dual CYP17/CYP11B2 inhibitors are proposed as a novel strategy for the treatment of prostate cancer to reduce risks of cardiovascular diseases. Via a combination of ligand- and structure-based approaches, a series of dual inhibitors were designed leading to the 2-(3-pyridyl)naphthalenes 10 and 11 with strong inhibition of both enzymes (IC50 values around 20 nM) and excellent selectivities over CYP11B1, CYP19, and CYP3A4. These compounds are considered as promising candidates for further in vivo evaluation.