cyclopent-3-enyl-(2-hydroxyphenyl)methanone | 646522-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclopent-3-enyl-(2-hydroxyphenyl)methanone
• 英文别名: (Cyclopent-3-en-1-yl)(2-hydroxyphenyl)methanone；cyclopent-3-en-1-yl-(2-hydroxyphenyl)methanone
• CAS: 646522-94-3
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: IYZPGSJFWZXKEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  cyclopent-3-enyl-(2-hydroxyphenyl)methanone 在 palladium diacetate 、 palladium dihydroxide 吡啶 、 氢氧化钾 、 sodium periodate 、 四氧化锇 、 三氟甲磺酸 、 (CH₂)5NCH₃O 、 Ph₃P(CH₂)3PPh₃ 、 硝酸 、 甲酸铵 、 potassium acetate 、 三乙酰氧基硼氢化钠 、 乙二醇 、 三乙胺 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 2,2,2-Trifluoro-1-(4-nitro-11-aza-tricyclo[7.3.1.0^2,7]trideca-2(7),3,5-trien-11-yl)-ethanone
  参考文献：
  名称：

  In pursuit of α4β2 nicotinic receptor partial agonists for smoking cessation: Carbon analogs of (−)-cytisine

  摘要：

  The preparation and biological activity of analogs of (-)-cytisine, an alpha 4 beta 2 nicotinic receptor partial agonist, are discussed. All-carbon-containing phenyl ring replacements of the pyridone ring system, generated via Heck cyclization protocols, exhibited weaker affinity and lower efficacy partial agonist profiles relative to (-)-cytisine. In vivo, selected compounds exhibit lower efficacy partial agonist profiles than that of (-)-cytisine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.036
• 作为产物：
  描述：

  cyclopent-3-enyl-(2-methoxy-phenyl)-methanone 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 生成 cyclopent-3-enyl-(2-hydroxyphenyl)methanone
  参考文献：
  名称：

  In pursuit of α4β2 nicotinic receptor partial agonists for smoking cessation: Carbon analogs of (−)-cytisine

  摘要：

  The preparation and biological activity of analogs of (-)-cytisine, an alpha 4 beta 2 nicotinic receptor partial agonist, are discussed. All-carbon-containing phenyl ring replacements of the pyridone ring system, generated via Heck cyclization protocols, exhibited weaker affinity and lower efficacy partial agonist profiles relative to (-)-cytisine. In vivo, selected compounds exhibit lower efficacy partial agonist profiles than that of (-)-cytisine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.036

文献信息

• Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights
  作者：Jotham W. Coe、Krista E. Bianco、Brian P. Boscoe、Paige R. Brooks、Eric D. Cox、Michael G. Vetelino

  DOI：10.1021/jo0352023

  日期：2003.12.1

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.
• In pursuit of α4β2 nicotinic receptor partial agonists for smoking cessation: Carbon analogs of (−)-cytisine
  作者：Jotham W. Coe、Michael G. Vetelino、Crystal G. Bashore、Michael C. Wirtz、Paige R. Brooks、Eric P. Arnold、Lorraine A. Lebel、Carol B. Fox、Steven B. Sands、Thomas I. Davis、David W. Schulz、Hans Rollema、F. David Tingley、Brian T. O’Neill

  DOI：10.1016/j.bmcl.2005.04.036

  日期：2005.6

  The preparation and biological activity of analogs of (-)-cytisine, an alpha 4 beta 2 nicotinic receptor partial agonist, are discussed. All-carbon-containing phenyl ring replacements of the pyridone ring system, generated via Heck cyclization protocols, exhibited weaker affinity and lower efficacy partial agonist profiles relative to (-)-cytisine. In vivo, selected compounds exhibit lower efficacy partial agonist profiles than that of (-)-cytisine. (c) 2005 Elsevier Ltd. All rights reserved.