4,7-dichloro-3H-isobenzofuran-1-one | 52043-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 4,7-dichloro-3H-isobenzofuran-1-one
• 英文别名: 4,7-dichlorophthalide；4,7-dichloro-phthalide；4,7-Dichlor-phthalid；4,7-dichloro-3H-2-benzofuran-1-one
• CAS: 52043-46-6
• 化学式: C₈H₄Cl₂O₂
• 分子量: 203.025
• InChiKey: LDBXTSFDQDITDX-UHFFFAOYSA-N

物化性质

• 沸点：
  403.7±45.0 °C(Predicted)
• 密度：
  1.562±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,7-dichloro-3H-isobenzofuran-1-one 在 palladium on activated charcoal sodium azide 、 硫酸 、 氢气 、 potassium nitrate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 23.75h， 生成
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2
• 作为产物：
  描述：

  3,6-二氯苯二甲酸酐 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到4,7-dichloro-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2

文献信息

• PRODUCTION METHOD OF HALOGEN-SUBSTITUTED PHTHALIDE
  申请人：Hagiya Koji

  公开号：US20120142946A1

  公开（公告）日：2012-06-07

  Disclosed is a method for producing a halogen-substituted phthalide, which includes a reaction step of reacting a halogen-substituted phthalic anhydride with sodium borohydride.

  本发明公开了一种制备卤代邻苯二酸酐的方法，其中包括将卤代邻苯二酸酐与硼氢化钠反应的反应步骤。
• Le Royer, Justus Liebigs Annalen der Chemie, 1887, vol. 238, p. 357
  作者：Le Royer

  DOI：——

  日期：——
• Villiger, Chemische Berichte, 1909, vol. 42, p. 3533
  作者：Villiger

  DOI：——

  日期：——
• Synthesis of phosphonate 3-phthalidyl esters as prodrugs for potential intracellular delivery of phosphonates
  作者：Qun Dang、Brian S. Brown、Paul D. van Poelje、Timothy J. Colby、Mark D. Erion

  DOI：10.1016/s0960-894x(99)00239-5

  日期：1999.6

  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.
• Guareschi, Chemische Berichte, 1886, vol. 19, p. 1155
  作者：Guareschi

  DOI：——

  日期：——