(2-phenylbenzofuran-3-yl)methanol | 263887-30-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (2-phenylbenzofuran-3-yl)methanol
• 英文别名: 3-(2-phenyl-1-benzofuran)carbinol；2-phenyl-3-benzofuranmethanol；(2-phenyl-benzofuran-3-yl)-methanol；(2-phenyl-1-benzofuran-3-yl)methanol
• CAS: 263887-30-5
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: HROPMIYNPWJHKG-UHFFFAOYSA-N

物化性质

• 沸点：
  322.5±9.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (2-phenylbenzofuran-3-yl)methanol 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 3-(2-bromobenzyl)-1-((2-phenylbenzofuran-3-yl)methyl)-1H-imidazol-3-ium bromide
  参考文献：
  名称：

  Synthesis and cytotoxic activities of novel hybrid 2-phenyl-3-alkylbenzofuran and imidazole/triazole compounds

  摘要：

  A series of novel hybrid compounds of 2-phenyl-3-alkylbenzofuran and imidazole or triazole were prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the 2-ethyl-imidazole ring, and substitution of the imidazolyl-3-position with a 2-bromobenzyl or naphthylacyl group, were vital for modulating inhibitory activity. In particular, hybrid compound 31 was found to be the most potent derivative with IC50 values of 0.08-0.55 mu M against five strains human tumor cell lines and was found to be more selective against breast carcinoma (MCF-7) and colon carcinoma (SW480) (IC50 values 40.8-fold and 40.1-fold lower than cisplatin (DDP)). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.001
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 4-二甲氨基吡啶 、 iron(III) chloride 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 水 、 cesium acetate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (2-phenylbenzofuran-3-yl)methanol
  参考文献：
  名称：

  通过铑（III）催化的氧化还原-中性CH官能化/环化反应级联合成3-亚烷基二氢苯并呋喃衍生物

  摘要：

  已经开发了一种有效的铑（III）催化的N-苯氧基乙酰胺与碳酸炔丙基酯的偶联反应，可通过CH功能化/级联环化反应生成3-亚烷基二氢苯并呋喃衍生物。该转变代表氧化还原中性过程，并具有在温和条件下形成三个新键的特征。

  DOI：

  10.1021/acs.orglett.5b03060

文献信息

• Rhodium(III)-Catalyzed Redox-Neutral Coupling of<i>N</i>-Phenoxyacetamides and Alkynes with Tunable Selectivity
  作者：Guixia Liu、Yangyang Shen、Zhi Zhou、Xiyan Lu

  DOI：10.1002/anie.201300881

  日期：2013.6.3

  Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)‐catalyzed CH functionalization of N‐phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho‐hydroxyphenyl‐substituted enamides or cyclization to deliver benzofurans with high selectivity (see scheme; Cp*=C5Me5).

  给它一个调整：一种新颖的氧化定向基团被用于铑（III）催化的开发Ç  h的官能Ñ与炔-phenoxyacetamides。反应条件的微小变化会导致邻-羟苯基取代的酰胺或环化反应以高选择性提供苯并呋喃（参见方案； Cp * = C 5 Me 5）。
• Thio-substituted tricyclic and bicyclic aromatic methanesulfinyl derivatives
  申请人：CEPHALON FRANCE

  公开号：EP1589016A1

  公开（公告）日：2005-10-26

  The present invention is related to chemical compositions, processes for the preparation thereof and uses of the composition. Particularly, the present invention relates to compositions of compounds of Formula (A): wherein Ar, Y, R1 and q are as defined herein; and their use in the treatment of diseases, including treatment of sleepiness, promotion of wakefulness, treatment of Parkinson's disease, cerebral ischemia, stroke, sleep apneas, eating disorders, stimulation of appetite and weight gain, treatment of attention deficit hyperactivity disorder ("ADHD"), enhancing function in disorders associated with hypofunctionality of the cerebral cortex, including, but not limited to, depression, schizophrenia, fatigue, in particular, fatigue associated with neurologic disease, such as multiple sclerosis, chronic fatigue syndrome, and improvement of cognitive dysfunction.

  本发明涉及化学组合物的制备过程及其用途。特别地，本发明涉及化合物(A)的组合物，其中Ar、Y、R1和q如本文中所定义；以及它们在治疗疾病中的应用，包括治疗嗜睡、促进清醒、治疗帕金森病、脑缺血、中风、睡眠呼吸暂停、进食障碍、刺激食欲和体重增加、治疗注意力缺陷多动障碍（“ADHD”）、增强与大脑皮层低功能相关的障碍的功能，包括但不限于抑郁症、精神分裂症、疲劳，尤其是与神经疾病如多发性硬化、慢性疲劳综合征相关的疲劳，以及改善认知功能障碍。
• Total synthesis of vibsanol, a benzofuran-type lignan
  作者：Atsushi Sakai、Toyohiko Aoyama、Takayuki Shioiri

  DOI：10.1016/s0040-4039(99)00714-5

  日期：1999.5

  Vibsanol (1), a benzofuran-type lignan isolated from the wood of Vibumum awabuki (Caprifoliaceae), was synthesized by the tandem cyclization of o-tert-butyldimethylsiloxydiarylalkyne with tetrabutylammonium fluoride and excess paraformaldehyde as the key step.

  Vibsanol（1）是一种从呋虫（Caprifoliaceae）的木材中分离出来的苯并呋喃型木脂素，是通过邻位叔丁基二甲基甲硅烷氧基二芳基炔烃与四丁基氟化铵和过量的多聚甲醛的关键步骤串联合成的。
• THIO-SUBSTITUTED TRICYCLIC AND BICYCLIC AROMATIC METHANESULFINYL DERIVATIVES
  申请人：Lesur Brigitte

  公开号：US20090105241A1

  公开（公告）日：2009-04-23

  The present invention is related to chemical compositions, processes for the preparation thereof and uses of the composition. Particularly, the present invention relates to compositions of compounds of Formula (A): wherein Ar, Y, R 1 and q are as defined herein; and their use in the treatment of diseases, including treatment of sleepiness, promotion of wakefulness, treatment of Parkinson's disease, cerebral ischemia, stroke, sleep apneas, eating disorders, stimulation of appetite and weight gain, treatment of attention deficit hyperactivity disorder (“ADHD”), enhancing function in disorders associated with hypofunctionality of the cerebral cortex, including, but not limited to, depression, schizophrenia, fatigue, in particular, fatigue associated with neurologic disease, such as multiple sclerosis, chronic fatigue syndrome, and improvement of cognitive dysfunction.

  本发明涉及化学组成物、其制备方法和组成物的用途。特别地，本发明涉及式（A）化合物的组成物：其中Ar、Y、R1和q如此定义；以及它们在治疗疾病中的应用，包括治疗嗜睡、促进清醒、治疗帕金森病、脑缺血、中风、睡眠呼吸暂停、进食障碍、刺激食欲和增重、治疗注意力缺陷多动障碍（“ADHD”）、增强与大脑皮层功能低下相关的疾病的功能，包括但不限于抑郁症、精神分裂症、疲劳，特别是与神经系统疾病相关的疲劳，如多发性硬化症、慢性疲劳综合征，以及改善认知功能。
• An Expeditious Synthesis of Vibsanol, a Benzofuran-Type Lignan from Viburnum awabuki
  作者：Takayuki Shioiri、Atsushi Sakai、Toyohiko Aoyama

  DOI：10.3987/com-99-s63

  日期：——