2,2,4,6,7-五甲基-3-苯基-3H-1-苯并呋喃 | 142874-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 2,2,4,6,7-五甲基-3-苯基-3H-1-苯并呋喃
• 英文名称: 2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran
• 英文别名: 2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran；Benzofuran, 2,3-dihydro-2,2,4,6,7-pentamethyl-3-phenyl-；2,2,4,6,7-pentamethyl-3-phenyl-3H-1-benzofuran
• CAS: 142874-60-0
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: USLXSFMNZAGGJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,4,6,7-五甲基-3-苯基-3H-1-苯并呋喃 在 palladium on activated charcoal 氢气 、 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.25h， 生成 YT-16
  参考文献：
  名称：

  5-Aminocoumarans:  Dual Inhibitors of Lipid Peroxidation and Dopamine Release with Protective Effects against Central Nervous System Trauma and Ischemia

  摘要：

  A series of 2,3-dihydro-5-benzofuranamines (5-aminocoumarans) were developed for the treatment of traumatic and ischemic central. nervous system (CNS) injury. Compounds within this class were extremely effective inhibitors of lipid peroxidation in vitro and antagonized excitatory behavior coupled with peroxidative injury induced by spinal intrathecal injection of FeCl2 (mouse-FeCl2-it assay) in vivo. Selected compounds were tested for antagonistic activity on methamphetamine (MAP)-induced hypermotility resulting from dopamine release in the mouse brain. Among the compounds synthesized, compound 26n (2,3-dihydro-2,4,6,7-tetramethyl-2-[(4-phenyl-1-piperidinyl)meth]-5-benzofuranamine) exhibited potent effects in these assays (inhibition of lipid peroxidation, IC50 = 0.07 mu M; mouse-FeCl2-it assay, ID50 = 10.4 mg/kg, po; MAP-induced hypermotility, 98% inhibition, 10 mg/kg, ip). The S-(+)-form of compound 26n dihydrochloride (TAK-218), which has 30 times more potent antagonistic activity on MAP-induced hypermotility than the R-(-)-form, improved more significantly the survival rate in the cerebral ischemia model (rat, 1-3 mg/kg, ip) during the period of 1-14 days after ischemia and decreased functional disorders in the traumatic brain injury model (rat, 0.1-1 mg/kg, ip) 3-14 days after injury. These results imply a role for dopamine in deterioration of CNS function after ischemic and traumatic injury. TAK-218 is a promising compound for the treatment of stroke and CNS trauma and is now under clinical investigation.

  DOI：

  10.1021/jm960411j
• 作为产物：
  描述：

  2-甲基-2-苯基丙腈 在 三氟甲磺酸 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2,2,4,6,7-五甲基-3-苯基-3H-1-苯并呋喃
  参考文献：
  名称：

  A convenient ring formation of 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans from phenols and 2-aryl-2,2-dialkylacetaldehydes

  摘要：

  A new and simple route for the preparation of 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans from phenols is described. In the presence of an acid catalyst phenols react with 2-aryl-2,2-dialkylacetaldehydes, prepared in good yield from 2-arylacetonitriles in 2 steps, to give 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans. Electron-donating substituents were required on the phenols in order to give 3-aryl-2,2dialkyl-2,3-dihydrobenzofurans in good yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.077

文献信息

• Aminocoumaran derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05376681A1

  公开（公告）日：1994-12-27

  A novel aminocoumaran derivatives of the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are a hydrogen atom, an acyl group, an alkoxycarbonyl group, an aliphatic group or aromatic group; R.sup.3 R.sup.4 and R.sup.5 are an optionally acylated hydroxyl optionally substituted amino group, alkoxy group or aliphatic group, or two of R.sup.3, R.sup.4 and R.sup.5 may be linked together to form a carbocyclic group; R.sup.6 and R.sup.7 are an aliphatic group and at least one of them has a methylene group at the .alpha.-position; R.sup.8 and R.sup.9 are a hydrogen atom or an aliphatic group or aromatic group, or a salt thereof is useful for medicines for preventing and treating various diseases such as arterial schleosis, hepatopathy, cerebrovascular diseases and the like.

  一种一般式（I）的新型氨基香豆素衍生物：##STR1##其中R.sup.1和R.sup.2是氢原子、酰基、烷氧羰基、脂肪基或芳香基；R.sup.3、R.sup.4和R.sup.5是可选酰化的羟基、可选取代的氨基、烷氧基或脂肪基，或者R.sup.3、R.sup.4和R.sup.5中的两个可以连接在一起形成一个碳环基团；R.sup.6和R.sup.7是脂肪基，其中至少一个在α-位置有一个亚甲基基团；R.sup.8和R.sup.9是氢原子或脂肪基或芳香基，或其盐，用于预防和治疗各种疾病，如动脉硬化、肝病、脑血管疾病等。
• Intermediates for pharmaceutically useful aminocoumaran derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05594154A1

  公开（公告）日：1997-01-14

  A novel aminocoumaran derivative of the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are a hydrogen atom, an acyl group, an alkoxycarbonyl group, an aliphatic group or aromatic group; R.sup.3, R.sup.4 and R.sup.5 are an optionally acylated hydroxyl optionally substituted amino group, alkoxy group or aliphatic group, or two of R.sup.3, R.sup.4 and R.sup.5 may be linked together to form a carbocyclic group; R.sup.6 and R.sup.7 are an aliphatic group and at least one of them has a methylene group at the .alpha.-position; R.sup.8 and R.sup.9 are a hydrogen atom or an aliphatic group or aromatic group, or a salt thereof is useful for medicines for preventing and treating various diseases such as arterial sclerosis, hepatopathy, cerebrovascular diseases and the like.

  一种新型氨基香豆素衍生物的一般式为（I）：##STR1## 其中，R.sup.1和R.sup.2是氢原子、酰基、烷氧羰基、脂肪基或芳基；R.sup.3、R.sup.4和R.sup.5是一个可选酰化的羟基、可选取代的氨基、烷氧基或脂肪基，或R.sup.3、R.sup.4和R.sup.5中的两个可连接在一起形成碳环基；R.sup.6和R.sup.7是脂肪基，其中至少一个在α位上有一个亚甲基；R.sup.8和R.sup.9是氢原子或脂肪基或芳基，或其盐，可用于预防和治疗各种疾病，如动脉硬化、肝病、脑血管疾病等。
• Process for producing benzofuran derivative
  申请人：——

  公开号：US20040210066A1

  公开（公告）日：2004-10-21

  A novel process for efficiently and easily producing a compound represented by the formula: 1 wherein ring A is a benzene ring that may be optionally further substituted in addition to the group represented by W, or a salt thereof; which comprises reacting a compound represented by the formula: 2 wherein R 1 and R 2 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, Y is a halogen atom, ring A is a benzene ring that may be optionally further substituted in addition to the group represented by Y and ring B is an optionally substituted benzene ring, or a salt thereof, with a compound represented by the formula: WH wherein W is 3 wherein ring C is an optionally substituted benzene ring, ring D is an optionally substituted 5- to 7-membered nitrogen-containing heterocyclic ring, R 3 is a hydrogen atom, an aliphatic hydrocarbon group containing an aromatic group or an acyl group, and R 4 is a hydrogen atom, an optionally substituted hydrocarbon group or an acyl group, or a salt thereof and thereafter, if necessary, deprotecting the resultant product, which is suitable for industrial production.

  一种高效且容易生产化合物的新工艺，该化合物的分子式为1，其中环A是苯环，除了W基团外还可以选择进一步取代，或其盐。该工艺包括将分子式为2的化合物与分子式为WH的化合物反应，其中R1和R2相同或不同，每个都是氢原子，可选择取代的碳氢基团或可选择取代的杂环基团，Y是卤素原子，环A是苯环，除了Y基团外还可以选择进一步取代，环B是可选择取代的苯环，或其盐。分子式为WH的化合物中，W是3，其中环C是可选择取代的苯环，环D是可选择取代的5-至7-成员含氮杂环，R3是氢原子，含芳香基团的脂肪烃基团或酰基，R4是氢原子，可选择取代的碳氢基团或酰基，或其盐。然后，必要时去保护所得产物，该产物适用于工业生产。
• Method of using aminocoumaran derivatives for treating cerebrovascular
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05478844A1

  公开（公告）日：1995-12-26

  A novel aminocoumaran derivatives of the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are a hydrogen atom, an acyl group, an alkoxycarbonyl group, an aliphatic group or aromatic group; R.sup.3, R.sup.4 and R.sup.5 are an optionally acylated hydroxyl optionally substituted amino group, alkoxy group or aliphatic group, or two of R.sup.3, R.sup.4 and R.sup.5 may be linked together to form a carbocyclic group; R.sup.6 and R.sup.7 are an aliphatic group and at least: one of them has a methylene group at the .alpha.-position; R.sup.8 and R.sup.9 are a hydrogen atom or an aliphatic group or aromatic group, or a salt thereof is useful for medicines for treating various diseases such as arterial sclerosis, hepatopathy, cerebrovascular diseases and the like.

  一种新型氨基香豆素衍生物，其通式为(I)：##STR1## 其中R.sup.1和R.sup.2为氢原子、酰基、烷氧基羰基、脂肪基或芳香族基；R.sup.3、R.sup.4和R.sup.5为可选的酰化羟基、可选的取代氨基、烷氧基或脂肪基，或者R.sup.3、R.sup.4和R.sup.5中的两个可以连接在一起形成一个环状碳骨架；R.sup.6和R.sup.7为脂肪基，至少其中一个在α-位上有一个亚甲基；R.sup.8和R.sup.9为氢原子、脂肪基或芳香族基，或其盐，用于治疗各种疾病，如动脉硬化、肝病、脑血管疾病等。
• Intermediates for the preparation of aminocoumaran derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05770772A1

  公开（公告）日：1998-06-23

  Disclosed are intermediates for the preparation of novel aminocoumaran derivatives of the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are a hydrogen atom, an acyl group, an alkoxycarbonyl group, an aliphatic group or aromatic group; R.sup.3, R.sup.4 and R.sup.5 are an optionally acylated hydroxyl, optionally substituted amino group, alkoxy group or aliphatic group, or two of R.sup.3, R.sup.4 and R.sup.5 may be linked together to form a carbocyclic group; R.sup.6 and R.sup.7 are an aliphatic group and at least one of them has a methylene group at the .alpha.-position; R.sup.8 and R.sup.9 are a hydrogen atom or an aliphatic group or aromatic group, or a salt thereof is useful for medicines for preventing and treating various diseases such as arterial sclerosis, hepatopathy, cerebrovascular diseases and the like.

  本发明涉及一种制备新型氨基香豆素衍生物的中间体，其一般式为(I)：##STR1## 其中，R.sup.1和R.sup.2是氢原子、酰基、烷氧羰基、脂肪基或芳香基；R.sup.3、R.sup.4和R.sup.5是可选酰化的羟基、可选取代的氨基、烷氧基或脂肪基，或R.sup.3、R.sup.4和R.sup.5中的两个可以连接在一起形成碳环基；R.sup.6和R.sup.7是脂肪基，其中至少一个在α-位上有一个亚甲基；R.sup.8和R.sup.9是氢原子或脂肪基或芳香基，或其盐，适用于预防和治疗各种疾病，如动脉硬化、肝病、脑血管疾病等。