3-bromo-7-methoxy-3H-2-benzofuran-1-one | 139360-85-3

• 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-bromo-7-methoxy-3H-2-benzofuran-1-one
• CAS: 139360-85-3
• 化学式: C₉H₇BrO₃
• 分子量: 243.057
• InChiKey: BIYJAAOMEHVZFR-UHFFFAOYSA-N

物化性质

• 沸点：
  362.7±42.0 °C(Predicted)
• 密度：
  1.682±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-bromo-7-methoxy-3H-2-benzofuran-1-one 在 sodium hydroxide 、 氢气 、 镍 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 90.0 ℃ 、506.62 kPa 条件下， 反应 19.75h， 生成 2-(2-Dimethylamino-ethoxy)-7-methoxy-isoindolo[2,1-a]indol-6-one
  参考文献：
  名称：

  New ligands at the melatonin binding site MT3

  摘要：

  The third melatonin binding site, MT3 is a non-classical one since it is not a seven transmembrane domains receptor, but an enzyme, quinone reductase 2. A major concern for the study of the physiological role of this site is the lack of specific ligands, permitting to more accurately dissect the pathways linked to the activation of MT3. Indeed, in the course of finding new ligands, we identified a new series of compounds with affinity to the binding site in the nM range, particularly 2,3-dimethoxy 7-hydroxy 10-methyl 5H 10H indeno(1,2-b)indol-10-one (DMHMIO), with a Ki of 190 pM. Based on slightly different and novel synthons compared to most of the compounds used in melatonin pharmacology studies, these compounds offer new perspective for the description of the melatonin pathways, so much more by not having any affinity towards the MTI and MT2 'classical' melatonin receptors. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.12.002
• 作为产物：
  描述：

  3-羟基苯二甲酸酐 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 3-bromo-7-methoxy-3H-2-benzofuran-1-one
  参考文献：
  名称：

  Synthesis of phosphonate 3-phthalidyl esters as prodrugs for potential intracellular delivery of phosphonates

  摘要：

  A new prodrug approach for intracellular delivery of phosphonates was developed via the synthesis of 3-phthalidyl esters of 1-naphthalenemethylphosphonate. This approach is advantageous over the traditional acyloxymethyl phosphonate prodrugs, because these prodrugs do not generate formaldehyde and have improved plasma half-lives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00239-5

文献信息

• Regiocontrolled synthesis of hydroxyphthalides. Synthesis of (.+-.)-isoochracinic acid and a zealeranone intermediate
  作者：Barry M. Trost、Gordon T. Rivers、Jeffrey M. Gold

  DOI：10.1021/jo01298a017

  日期：1980.5