6-chloro-1-(2-hydroxyphenyl)-1-hexanone | 501083-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-chloro-1-(2-hydroxyphenyl)-1-hexanone
• 英文别名: 6-chloro-1-(2-hydroxyphenyl)hexan-1-one
• CAS: 501083-62-1
• 化学式: C₁₂H₁₅ClO₂
• 分子量: 226.703
• InChiKey: OAFJLSOELVBXPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-哌嗪-1,2-苯异唑 、 6-chloro-1-(2-hydroxyphenyl)-1-hexanone 以 乙腈 为溶剂， 以40%的产率得到6-(4-Benzo[d]isoxazol-3-yl-piperazin-1-yl)-1-(2-hydroxy-phenyl)-hexan-1-one
  参考文献：
  名称：

  Synthesis and Structure−Affinity Relationships of 1-[ω-(4-Aryl-1-piperazinyl)alkyl]-1-aryl Ketones as 5-HT₇ Receptor Ligands

  摘要：

  Structural requirements for 5-HT7 receptor affinity and selectivity over that for the 5-HT1A receptor were studied on a series of 1-[omega-(4-aryl-1-piperazinyl)alkyl] - I-aryl ketones. The presence of a hydroxy or methoxy substituent on aryl ketone moiety, alkyl chain length, and the nature of N-1-piperazine substituent were explored. 6-[4-(3-Benzisoxazolyl)-l-piperazinyl]-1-(2-hydroxyphenyl)-1-hexanone (40) and its methoxy analogue 43 exhibited high 5-HT7 receptor affinities (K-i = 2.93 nM and 0.90 nM, respectively) and agonist properties when tested for 5-HT7 receptor-mediated relaxation of substance P-induced guinea-pig ileum contraction.

  DOI：

  10.1021/jm020994z
• 作为产物：
  描述：

  5-氯-N-戊基溴化镁 在 jones reagent 、 氢溴酸 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 6-chloro-1-(2-hydroxyphenyl)-1-hexanone
  参考文献：
  名称：

  Synthesis and Structure−Affinity Relationships of 1-[ω-(4-Aryl-1-piperazinyl)alkyl]-1-aryl Ketones as 5-HT₇ Receptor Ligands

  摘要：

  Structural requirements for 5-HT7 receptor affinity and selectivity over that for the 5-HT1A receptor were studied on a series of 1-[omega-(4-aryl-1-piperazinyl)alkyl] - I-aryl ketones. The presence of a hydroxy or methoxy substituent on aryl ketone moiety, alkyl chain length, and the nature of N-1-piperazine substituent were explored. 6-[4-(3-Benzisoxazolyl)-l-piperazinyl]-1-(2-hydroxyphenyl)-1-hexanone (40) and its methoxy analogue 43 exhibited high 5-HT7 receptor affinities (K-i = 2.93 nM and 0.90 nM, respectively) and agonist properties when tested for 5-HT7 receptor-mediated relaxation of substance P-induced guinea-pig ileum contraction.

  DOI：

  10.1021/jm020994z

文献信息

• Nickel-Catalyzed Directed Cross-Electrophile Coupling of Phenolic Esters with Alkyl Bromides
  作者：Feiyan Yang、Decai Ding、Chuan Wang

  DOI：10.1021/acs.orglett.0c03342

  日期：2020.12.4

  electrophilic acyl source in the reaction with diverse primary and secondary unactivated alkyl bromides. The cleavage of the relatively inert C–O bond is facilitated by the neighboring coordinating hydroxyl or sulfonamide moiety. By circumventing the use of pregenerated organometallics, this method allows efficient preparation of a variety of o-hydroxyl and tosyl-protected o-amino aryl ketones with high compatibility

  在本文中，我们证明了在各种伯和仲未活化烷基溴的反应中，成功使用了强健的酚酯作为亲电子酰基源。相邻的羟基或磺酰胺部分可促进相对惰性的C-O键的裂解。通过避免使用预生成的有机金属，该方法可以有效地制备具有高相容性和广泛功能的各种邻羟基和甲苯磺酰基保护的邻氨基芳基酮。