3-phenyl-2-benzo<2,3>furanyl-2-ethanol | 27407-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-phenyl-2-benzo<2,3>furanyl-2-ethanol
• 英文别名: 2-(3-phenylbenzofuran-2-yl)ethan-1-ol；2-(3-Phenyl-benzofuran-2-yl)-ethanol；2-(3-phenyl-benzofuran-2-yl)-ethanol；2-(3-Phenyl-1-benzofuran-2-yl)ethanol
• CAS: 27407-78-9
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: NIPNGLUWTSVBNO-UHFFFAOYSA-N

物化性质

• 沸点：
  418.1±40.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-benzo<2,3>furanyl-2-ethanol 在 lithium hydroxide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 79.5h， 生成 1-<2-(3-phenyl-2-benzofuranyl)ethyl>-3-piperidinecarboxylic acid
  参考文献：
  名称：

  Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake

  摘要：

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.

  DOI：

  10.1021/jm00100a032
• 作为产物：
  描述：

  [2-(3-Hydroxypropoxy)phenyl]-phenylmethanone 反应 2.5h， 以82%的产率得到3-phenyl-2-benzo<2,3>furanyl-2-ethanol
  参考文献：
  名称：

  光使羰基与非酸性亚甲基脱氢缩合：苯并呋喃的合成

  摘要：

  羰基与非酸性亚甲基（例如与杂原子和烯丙基类型相邻的亚甲基）缩合生成C = C键是具有挑战性的，但非常需要。发明新颖的方法可以完成...

  DOI：

  10.1039/c6cc07626b

文献信息

• HETEROCYCLIC COMPOUNDS AS PI3 KINASE INHIBITORS
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2673269A1

  公开（公告）日：2013-12-18
• [EN] HETEROCYCLIC COMPOUNDS AS PI3 KINASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DE PI3 KINASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012107465A1

  公开（公告）日：2012-08-16

  Formula I compounds, including stereoisomers, geometric isomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological disorders, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.
• Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake
  作者：Michael R. Pavia、Sandra J. Lobbestael、David Nugiel、Daniel R. Mayhugh、Vlad E. Gregor、Charles P. Taylor、Roy D. Schwarz、Laura Brahce、Mark G. Vartanian

  DOI：10.1021/jm00100a032

  日期：1992.10

  The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of <1 muM (including 5, Table 1; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.
• Dehydrative condensation of carbonyls with non-acidic methylenes enabled by light: synthesis of benzofurans
  作者：Wenbo Liu、Ning Chen、Xiaobo Yang、Lu Li、Chao-Jun Li

  DOI：10.1039/c6cc07626b

  日期：——

  Condensation of carbonyls with non-acidic methylenes such as those adjacent to heteroatoms and allylic types to generate C=C bonds is challenging but highly desirable. Inventing novel methods that can accomplish...

  羰基与非酸性亚甲基（例如与杂原子和烯丙基类型相邻的亚甲基）缩合生成C = C键是具有挑战性的，但非常需要。发明新颖的方法可以完成...