2,3-dihydro-2,2,4,6,7-pentamethyl-3-dimethylaminomethyl-1-benzofuran-5-ol | 153490-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydro-2,2,4,6,7-pentamethyl-3-dimethylaminomethyl-1-benzofuran-5-ol
• 英文别名: 3-[(dimethylamino)methyl]-2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-ol
• CAS: 153490-66-5
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: RUQLJSWBLYIYAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸甲酯 、 2,3-dihydro-2,2,4,6,7-pentamethyl-3-dimethylaminomethyl-1-benzofuran-5-ol 以 乙酸乙酯 、 乙腈 为溶剂， 生成 2,3-DIHYDRO-5-HYDROXY-N,N,N-2,2,4,6,7-OCTAMETHYL-1-BENZOFURAN-3-METHANAMINIUM 4-METHYLBENZENSULFONATE
  参考文献：
  名称：

  Derivatives of 2,3-dihydro benzofuranols

  摘要：

  2,3-二氢-5-苯并呋喃醇的衍生物，其中间体以及用于它们制备的有用过程。这些化合物是自由基清除剂，在治疗能够通过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方面具有用处。

  公开号：

  US05721233A1
• 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 、 dimethyl sulfide borane 、 bromotriphenylphosphonium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 313.83h， 生成 2,3-dihydro-2,2,4,6,7-pentamethyl-3-dimethylaminomethyl-1-benzofuran-5-ol
  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

• 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
• US5721233A
  申请人：——

  公开号：US5721233A

  公开（公告）日：1998-02-24
• [EN] NOVEL DERIVATIVES OF 2,3-DIHYDRO-2,2,4,6,7-PENTAALKYL-5-BENZOFURANOLS<br/>[FR] NOUVEAUX DERIVES DE 2,3-DIHYDRO-2,2,4,6,7-PENTAALKYL-5-BENZOFURANOLS
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：WO1993020057A1

  公开（公告）日：1993-10-14

  (EN) 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.(FR) Dérivés de 2,3-dihydro-5-benzofuranols, ainsi que leurs intermédiaires et procédés efficaces pour leur préparation. Ces composés sont des piégeurs de radicaux libres et sont efficaces dans le traitement d'états pouvant se traiter au moyen de piégeurs de radicaux libres, tels que les attaques, les traumatismes du système nerveux et les lésions provoquées par le rétablissement de l'irrigation sanguine après infarctus.
• 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
  作者：J. Martin Grisar、Frank N. Bolkenius、Margaret A. Petty、Joelle Verne

  DOI：10.1021/jm00003a008

  日期：1995.2

  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.
• 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-苯并呋喃醇的衍生物，其中间体以及用于它们制备的有用过程。这些化合物是自由基清除剂，在治疗能够通过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方面具有用处。