5-chloro-4'-fluoro-2'-hydroxyvalerophenone | 149412-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-4'-fluoro-2'-hydroxyvalerophenone
• 英文别名: 5-Chloro-1-(4-fluoro-2-hydroxyphenyl)-1-pentanone；5-chloro-1-(4-fluoro-2-hydroxyphenyl)pentan-1-one
• CAS: 149412-46-4
• 化学式: C₁₁H₁₂ClFO₂
• 分子量: 230.666
• InChiKey: JXQRROYWADEUBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-4'-fluoro-2'-hydroxyvalerophenone 在 吡啶 、 盐酸羟胺 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 59.5h， 生成 6-fluoro-3-[4-(5-fluoro-9,16-diazatetracyclo[10.3.1.02,10.03,8]hexadeca-2(10),3(8),4,6-tetraen-16-yl)butyl]-1,2-benzoxazole
  参考文献：
  名称：

  Bridged .gamma.-carbolines and derivatives possessing selective and combined affinity for 5-HT2 and D2 receptors

  摘要：

  A series of 5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indoles and 6,7,8,9,10,11-hexahydro-7,-11-imino-5H-cyclooct[b]indoles was prepared. Structural modifications of the lead compound, 11-[4-(4-fluorobenzoyl)propyl]-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole (5, K(i) = 0.82 nM vs [H-3]ketanserin) enabled the identification of the functionality necessary for high affinity at serotonin 5-HT2 and dopamine D2 receptors in ligand binding studies. The indole ring, as well as the benzoyl or isosteric benzisoxazole moiety, were essential for high affinity. Variations of the length of the side chains resulted in ligands having either selective affinity for the 5-HT2 receptor or a combination of 5-HT2 and D2 affinity. In vivo binding studies were performed on selected members in this series. The most potent member, 2-fluoro-11-[4-(4-fluorobenzoyl)butyl]-5,6,7,8,9,-10-hexahydro-7,10-iminocyclohept[b]indole (36) had an ED50 of <1 mg/kg at the 5-HT2 and D2 receptors following oral administration.

  DOI：

  10.1021/jm00062a023
• 作为产物：
  描述：

  5-氯代戊酰氯 、 3-氟苯酚 在 三氟化硼乙醚 作用下， 反应 20.25h， 以39.3%的产率得到5-chloro-4'-fluoro-2'-hydroxyvalerophenone
  参考文献：
  名称：

  Bridged .gamma.-carbolines and derivatives possessing selective and combined affinity for 5-HT2 and D2 receptors

  摘要：

  A series of 5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indoles and 6,7,8,9,10,11-hexahydro-7,-11-imino-5H-cyclooct[b]indoles was prepared. Structural modifications of the lead compound, 11-[4-(4-fluorobenzoyl)propyl]-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole (5, K(i) = 0.82 nM vs [H-3]ketanserin) enabled the identification of the functionality necessary for high affinity at serotonin 5-HT2 and dopamine D2 receptors in ligand binding studies. The indole ring, as well as the benzoyl or isosteric benzisoxazole moiety, were essential for high affinity. Variations of the length of the side chains resulted in ligands having either selective affinity for the 5-HT2 receptor or a combination of 5-HT2 and D2 affinity. In vivo binding studies were performed on selected members in this series. The most potent member, 2-fluoro-11-[4-(4-fluorobenzoyl)butyl]-5,6,7,8,9,-10-hexahydro-7,10-iminocyclohept[b]indole (36) had an ED50 of <1 mg/kg at the 5-HT2 and D2 receptors following oral administration.

  DOI：

  10.1021/jm00062a023

文献信息

• Bridged .gamma.-carbolines and derivatives possessing selective and combined affinity for 5-HT2 and D2 receptors
  作者：Richard E. Mewshaw、Lisa S. Silverman、Rose M. Mathew、Carl Kaiser、Ronald G. Sherrill、Menyan Cheng、Carol W. Tiffany、E. William Karbon、Michael A. Bailey

  DOI：10.1021/jm00062a023

  日期：1993.5

  A series of 5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indoles and 6,7,8,9,10,11-hexahydro-7,-11-imino-5H-cyclooct[b]indoles was prepared. Structural modifications of the lead compound, 11-[4-(4-fluorobenzoyl)propyl]-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole (5, K(i) = 0.82 nM vs [H-3]ketanserin) enabled the identification of the functionality necessary for high affinity at serotonin 5-HT2 and dopamine D2 receptors in ligand binding studies. The indole ring, as well as the benzoyl or isosteric benzisoxazole moiety, were essential for high affinity. Variations of the length of the side chains resulted in ligands having either selective affinity for the 5-HT2 receptor or a combination of 5-HT2 and D2 affinity. In vivo binding studies were performed on selected members in this series. The most potent member, 2-fluoro-11-[4-(4-fluorobenzoyl)butyl]-5,6,7,8,9,-10-hexahydro-7,10-iminocyclohept[b]indole (36) had an ED50 of <1 mg/kg at the 5-HT2 and D2 receptors following oral administration.