5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid | 161528-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid
• 英文别名: 5-acetoxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-carboxylic acid；5-acetyloxy-2,2,4,6,7-pentamethyl-3H-1-benzofuran-3-carboxylic acid
• CAS: 161528-10-5
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: SZWLTZXHASLOKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (S)-2,3-dihydro-5-hydroxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-methanol
  参考文献：
  名称：

  2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma

  摘要：

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.

  DOI：

  10.1021/jm00003a008
• 作为产物：
  描述：

  6-hydroxy-2,2,5,7,8-pentamethylchroman-4-one 在 吡啶 、 sodium hydroxide 、 thallium(III) nitrate trihydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 144.83h， 生成 5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid
  参考文献：
  名称：

  2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma

  摘要：

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.

  DOI：

  10.1021/jm00003a008

文献信息

• Process for preparing 2,3-dihydro-benzofuranol derivatives
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05698696A1

  公开（公告）日：1997-12-16

  This invention relates to a novel process for preparing 2,3-dihydro-benzofuranol derivatives and to the novel intermediates produced thereby.

  本发明涉及一种制备2,3-二氢苯并呋喃醇衍生物的新工艺，以及由此产生的新中间体。
• [EN] NOVEL PROCESS FOR PREPARING 2,3-DIHYDRO-BENZOFURANOL DERIVATIVES<br/>[FR] NOUVEAU PROCEDE DE PREPARATION DE DERIVES DU 2,3-DIHYDRO-BENZOFURANOL
  申请人：HOECHST MARION ROUSSEL, INC.

  公开号：WO1996028437A1

  公开（公告）日：1996-09-19

  (EN) This invention relates to a novel process for preparing 2,3-dihydro-benzofuranol derivatives and to the novel intermediates produced thereby.(FR) L'invention porte sur un nouveau procédé de préparation de dérivés du 2,3-dihydro-benzofuranol et sur de nouveaux intermédiaires produits à cet effet.

  这项发明涉及一种制备2,3-二氢苯并呋喃醇衍生物的新工艺，以及由此产生的新中间体。
• Derivatives of 2,3-dihydro benzofuranols
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05721233A1

  公开（公告）日：1998-02-24

  Derivatives of 2,3-dihydro-5-benzofuranol, intermediates thereof, and processes useful for their preparation. These compounds are free radical scavengers and are useful in the treatment of conditions capable of being treated by free radical scavengers, such as stroke, nervous system trauma and reperfusion damage.

  2,3-二氢-5-苯并呋喃醇及其中间体的衍生物和其制备方法。这些化合物是自由基清除剂，可用于治疗能够被自由基清除剂治疗的疾病，如中风、神经系统创伤和再灌注损伤。
• NOVEL DERIVATIVES OF 2,3-DIHYDRO-2,2,4,6,7-PENTAALKYL-5-BENZOFURANOLS
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0635009B1

  公开（公告）日：1997-09-17
• NOVEL PROCESS FOR PREPARING 2,3-DIHYDRO-BENZOFURANOL DERIVATIVES
  申请人：HOECHST MARION ROUSSEL, INC.

  公开号：EP0813530A1

  公开（公告）日：1997-12-29