(4-chlorophenyl)(2-fluoropyridin-3-yl)methanol | 944654-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-chlorophenyl)(2-fluoropyridin-3-yl)methanol
• 英文别名: (4-Chlorophenyl)-(2-fluoropyridin-3-yl)methanol
• CAS: 944654-20-0
• 化学式: C₁₂H₉ClFNO
• 分子量: 237.661
• InChiKey: ZREVTBINFMBOSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.12
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)(2-fluoropyridin-3-yl)methanol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4-chlorophenyl)(2-fluoropyridin-3-yl)methanone
  参考文献：
  名称：

  Design, Synthesis, and Activity of a Series of Arylpyrid-3-ylmethanones as Type I Positive Allosteric Modulators of α7 Nicotinic Acetylcholine Receptors

  摘要：

  A series of novel arylpyrid-3-ylmethanones (7a-aa) were designed as modulators of alpha 7 nicotinic acetylcholine receptors (nAChRs). The methanones were found to be type I positive allosteric modulators (PAMs) of human alpha 7 nAChRs expressed in Xenopus ooctyes. Structure-activity relationship (SAR) studies resulted in the identification of compound 7v as a potent and efficacious type I PAM with maximum modulation of a nicotine EC5 response of 1200% and EC50 = 0.18 mu M. Compound 7z was active in reversing the effect of scopolamine in the novel object recognition (NOR) paradigm with a minimum effective ip dose of 1.0 mg/kg (2.7 mu mol/kg). This effect was blocked by the selective alpha 7 nAChR antagonist methyllycaconitine (MLA). These compounds are nAChRs that may have therapeutic value in restoring impaired sensory Alzheimer's disease. potent type I positive allosteric modulators of alpha 7 gating and cognitive deficits in schizophrenia and Alzheimer's disease.

  DOI：

  10.1021/jm400704g
• 作为产物：
  描述：

  2-氟吡啶 、 4-氯苯甲醛 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.51h， 以96%的产率得到(4-chlorophenyl)(2-fluoropyridin-3-yl)methanol
  参考文献：
  名称：

  在Mg，Zn，Cu或La卤化物存在下使用TMPLi对官能化芳烃和杂芳烃进行连续流捕集的实用金属化

  摘要：

  各种芳烃和杂芳烃原位涉及一种用金属盐（氯化锌俘获的流动金属化2 ⋅2的LiCl，氯化镁2，CuCN⋅2的LiCl，的LaCl 3 ⋅2的LiCl）非常方便的条件下（0℃，40秒）是报告。生成的Mg，Zn，Cu或La有机物质被各种亲电试剂高产率捕集。在一些情况下，获得了异常的动力学控制的区域选择性。仅通过延长反应时间就可以按比例放大所有这些金属流，而无需进一步优化。这种流动金属化的反应范围比相应的分批程序的反应范围大得多。

  DOI：

  10.1002/anie.201502393

文献信息

• Practical Continuous-Flow Trapping Metalations of Functionalized Arenes and Heteroarenes Using TMPLi in the Presence of Mg, Zn, Cu, or La Halides
  作者：Matthias R. Becker、Paul Knochel

  DOI：10.1002/anie.201502393

  日期：2015.10.12

  The flow metalation of various arenes and heteroarenes involving an in situ trapping with metal salts (ZnCl2⋅2 LiCl, MgCl2, CuCN⋅2 LiCl, LaCl3⋅2 LiCl) under very convenient conditions (0 °C, 40 s) is reported. The resulting Mg, Zn, Cu, or La organic species are trapped with various electrophiles in high yields. In several cases, unusual kinetically controlled regioselectivities are obtained. All these

  各种芳烃和杂芳烃原位涉及一种用金属盐（氯化锌俘获的流动金属化2 ⋅2的LiCl，氯化镁2，CuCN⋅2的LiCl，的LaCl 3 ⋅2的LiCl）非常方便的条件下（0℃，40秒）是报告。生成的Mg，Zn，Cu或La有机物质被各种亲电试剂高产率捕集。在一些情况下，获得了异常的动力学控制的区域选择性。仅通过延长反应时间就可以按比例放大所有这些金属流，而无需进一步优化。这种流动金属化的反应范围比相应的分批程序的反应范围大得多。
• Design, Synthesis, and Activity of a Series of Arylpyrid-3-ylmethanones as Type I Positive Allosteric Modulators of α7 Nicotinic Acetylcholine Receptors
  作者：Derk J. Hogenkamp、Thomas A. Ford-Hutchinson、Wen-Yen Li、Edward R. Whittemore、Ryan F. Yoshimura、Minhtam B. Tran、Timothy B. C. Johnstone、Gavin D. Bascom、Hannah Rollins、Lena Lu、Kelvin W. Gee

  DOI：10.1021/jm400704g

  日期：2013.11.14

  A series of novel arylpyrid-3-ylmethanones (7a-aa) were designed as modulators of alpha 7 nicotinic acetylcholine receptors (nAChRs). The methanones were found to be type I positive allosteric modulators (PAMs) of human alpha 7 nAChRs expressed in Xenopus ooctyes. Structure-activity relationship (SAR) studies resulted in the identification of compound 7v as a potent and efficacious type I PAM with maximum modulation of a nicotine EC5 response of 1200% and EC50 = 0.18 mu M. Compound 7z was active in reversing the effect of scopolamine in the novel object recognition (NOR) paradigm with a minimum effective ip dose of 1.0 mg/kg (2.7 mu mol/kg). This effect was blocked by the selective alpha 7 nAChR antagonist methyllycaconitine (MLA). These compounds are nAChRs that may have therapeutic value in restoring impaired sensory Alzheimer's disease. potent type I positive allosteric modulators of alpha 7 gating and cognitive deficits in schizophrenia and Alzheimer's disease.