2,2,4,6,7-五甲基-3-(4-甲基苯基)-3H-1-苯并呋喃 | 142874-62-2

• 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-(4-甲基苯基)-3H-1-苯并呋喃
• 英文名称: 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran
• 英文别名: 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydrobenzofuran；Benzofuran, 2,3-dihydro-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-；2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-3H-1-benzofuran
• CAS: 142874-62-2
• 化学式: C₂₀H₂₄O
• 分子量: 280.41
• InChiKey: LWTJKYLZMBZIJB-UHFFFAOYSA-N

物化性质

• 沸点：
  377.6±42.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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-(4-甲基苯基)-3H-1-苯并呋喃 在 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 0.25h， 生成 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-5-nitro-2,3-dihydrobenzofuran
  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-1-(4-甲基苯基)-2-(2,3,5-三甲基苯氧基)丙烷-1-酮 在 sodium tetrahydroborate 、 三氟甲磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2,2,4,6,7-五甲基-3-(4-甲基苯基)-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

• [EN] AZO COMPOUNDS AND PROCESS FOR PRODUCTION THEREOF<br/>[FR] COMPOSÉS AZOÏQUES, PROCÉDÉ DE PRODUCTION DE CEUX-CI
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2006022311A1

  公开（公告）日：2006-03-02

  A process for the production of an aromatic azo compound having a 2,3-dihydrobenzofuran ring bearing a diazo group at the 5-position of the ring by conducting the diazo coupling of a 2,3-dihydrobenzofuran derivative represented by the general formula (II): (II) [wherein R1 and R2 are each independently C1-6 alkyl; R3 is optionally substituted aryl; and R4, R5 and R6 are each independently hydrogen, C1-6 alkyl, halogeno, C1-6 alkoxy, or C1-6 alkylthio] with a benzenediazonium salt having an electron-withdrawing group at the p- and/or o-position in a mixed solvent composed of water and a polar organic solvent.

  一种生产具有2,3-二氢苯并呋喃环，在环的5-位上带有重氮基团的芳香偶氮化合物的方法，通过在由水和极性有机溶剂组成的混合溶剂中，将一种由通式（II）表示的2,3-二氢苯并呋喃衍生物进行重氮偶联，其中（II）[其中R1和R2各自独立地是C1-6烷基；R3是可选的取代芳基；R4、R5和R6各自独立地是氢、C1-6烷基、卤素、C1-6烷氧基或C1-6烷硫基]与在p-位和/或o-位具有带电子吸引基团的苯二重氮盐。
• 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。
• Azo Compounds and Process for Production Thereof
  申请人：Ikemoto Tomomi

  公开号：US20080009539A1

  公开（公告）日：2008-01-10

  A process for the production of an aromatic azo compound having a 2,3-dihydrobenzofuran ring bearing a diazo group at the 5-position of the ring by conducting the diazo coupling of a 2,3-dihydrobenzofuran derivative represented by the general formula (II): [wherein R 1 and R 2 are each independently C 1-6 alkyl; R 3 is optionally substituted aryl; and R 4 , R 5 and R 6 are each independently hydrogen, C 1-6 alkyl, halogeno, C 1-6 alkoxy, or C 1-6 alkylthio] with a benzenediazonium salt having an electron-withdrawing group at the p- and/or o-position in a mixed solvent composed of water and a polar organic solvent.

  一种制备含有2,3-二氢苯并呋喃环，在环上的5位带有重氮基团的芳香偶氮化合物的方法，通过在由水和极性有机溶剂组成的混合溶剂中，将通式（II）所代表的2,3-二氢苯并呋喃衍生物[其中R1和R2各自独立地是C1-6烷基；R3是可选的取代芳基；R4、R5和R6各自独立地是氢、C1-6烷基、卤素、C1-6烷氧基或C1-6烷硫基]与在p-位和/或o-位具有电子吸引基团的苯基重氮盐进行重氮偶联反应。
• Azo compounds and process for production thereof
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US07521545B2

  公开（公告）日：2009-04-21

  A process for the production of an aromatic azo compound having a 2,3-dihydrobenzofuran ring bearing a diazo group at the 5-position of the ring by conducting the diazo coupling of a 2,3-dihydrobenzofuran derivative represented by the general formula (II): [wherein R1 and R2 are each independently C1-6 alkyl; R3 is optionally substituted aryl; and R4, R5 and R6 are each independently hydrogen, C1-6 alkyl, halogeno, C1-6 alkoxy, or C1-6 alkylthio] with a benzenediazonium salt having an electron-withdrawing group at the p- and/or o-position in a mixed solvent composed of water and a polar organic solvent.

  一种制备含有2,3-二氢苯并呋喃环，在环的5位携带重氮基团的芳香偶氮化合物的方法，通过在由水和极性有机溶剂组成的混合溶剂中，将一种由通式（II）表示的2,3-二氢苯并呋喃衍生物与在p-和/或o-位置具有电子吸引基团的苯基重氮盐进行重氮偶联。其中，式中R1和R2各自独立地表示C1-6烷基；R3表示可选取代的芳基；R4、R5和R6各自独立地表示氢、C1-6烷基、卤素、C1-6烷氧基或C1-6烷硫基。
• Aminocoumaran derivatives, their production and use
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0483772A1

  公开（公告）日：1992-05-06

  A novel aminocoumaran derivatives of the general formula (I): wherein R¹ and R² are a hydrogen atom, an acyl group, an alkoxycarbonyl group, an aliphatic group or aromatic group; R³, R⁴ and R⁵ are an optionally acylated hydroxyl, optionally substituted amino group, alkoxy group or aliphatic group, or two of R³, R⁴ and R⁵ may be linked together to form a carbocyclic group; R⁶ and R⁷ are an aliphatic group and at least one of them has a methylene group at the α-position; R⁸ and R⁹ 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.

  通式 (I) 的新型氨基香豆素衍生物： 其中 R¹ 和 R² 是氢原子、酰基、烷氧羰基、脂肪族基团或芳香族基团；R³、R⁴ 和 R⁵ 是任选酰化的羟基、任选取代的氨基、烷氧基或脂肪族基团，或者两个 R³、R⁴ 和 R⁵ 可以连接在一起形成碳环基团；R⁶ 和 R⁷ 是脂肪族基团，且其中至少一个在 α 位上有亚甲基； R⁸ 和 R⁹ 是氢原子或脂肪族基团或芳香族基团，或其盐可用于预防和治疗动脉硬化、肝病、脑血管疾病等各种疾病的药物。