2-carbomethoxy-3-fluoronaphthalene | 1718-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-carbomethoxy-3-fluoronaphthalene
• 英文别名: 2-fluoro-3-carbomethoxynaphthalene；methyl 3-fluoro-2-naphthoate；3-Fluor-2-naphthoesaeure-methylester；methyl 3-fluoronaphthalene-2-carboxylate
• CAS: 1718-17-8
• 化学式: C₁₂H₉FO₂
• 分子量: 204.201
• InChiKey: CMHPMYBDWOALOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  317.7±25.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-carbomethoxy-3-fluoronaphthalene 在 吡啶 、 sodium hydroxide 、 氯化亚砜 作用下， 生成 3-fluoro-2-naphthoyl chloride
  参考文献：
  名称：

  Adcock,W. et al., Australian Journal of Chemistry, 1971, vol. 24, p. 1829 - 1838

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基-2-萘甲酸 在 tetrafluoroboric acid 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.33h， 生成 2-carbomethoxy-3-fluoronaphthalene
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Conformationally Constrained Analogues of Naphthol AS-E as Inhibitors of CREB-Mediated Gene Transcription

  摘要：

  Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.

  DOI：

  10.1021/jm300043c

文献信息

• Synthesis of monofluorobenzo[c]phenanthrenes
  作者：Yitzhak Ittah、Donald M. Jerina

  DOI：10.1016/s0022-1139(00)82388-x

  日期：1980.8

  Synthesis of 1-, 2-, 3- and 4-fluorobenzo[c]phenanthrenes by photocyclization of appropriate β-naphth-l-yl fluorostyrenes is described. An improved synthesis of 6-fluorobenzo[c]phenanthrene was developed. Partial photochemical debromination occured upon cyclization of 2-bromo-7-fluorobenzo[c]phenanthrene.

  描述了通过适当的β-萘-1-基氟苯乙烯的光环化来合成1-，2-，3-和4-氟苯并[c]菲。开发了一种改进的6-氟苯并[c]菲的合成方法。2-溴-7-氟苯并[c]菲环化后发生部分光化学脱溴。
• Synthesis of the K-region monofluoro- and difluorobenzo[c]phenanthrenes
  作者：Seid Mirsadeghi、Ganesh K. B. Prasad、Noel Whittaker、Dhiren R. Thakker

  DOI：10.1021/jo00274a026

  日期：1989.6
• ITTAH Y.; JERINA D. M., J. FLUOR. CHEM., 1980, 16, NO 2, 137-144
  作者：ITTAH Y.、 JERINA D. M.

  DOI：——

  日期：——
• Adcock,W. et al., Australian Journal of Chemistry, 1971, vol. 24, p. 1829 - 1838
  作者：Adcock,W. et al.

  DOI：——

  日期：——
• Design, Synthesis, and Biological Evaluation of Conformationally Constrained Analogues of Naphthol AS-E as Inhibitors of CREB-Mediated Gene Transcription
  作者：Min Jiang、Bingbing X. Li、Fuchun Xie、Frances Delaney、Xiangshu Xiao

  DOI：10.1021/jm300043c

  日期：2012.4.26

  Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.