N-(4-hydroxy-2,3-dimethyl-phenyl)acetamide | 2011-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-hydroxy-2,3-dimethyl-phenyl)acetamide
• 英文别名: 4-acetamido-1-hydroxy-2,3-dimethylbenzene；4-hydroxy-2,3-dimethylacetanilide；4-acetamido-2,3-dimethylphenol；4-Acetylamino-2,3-dimethylphenol；4-Acetamino-2,3-dimethyl-phenol；Dimethyl-4-hydroxyacetanilide；N-(4-hydroxy-2,3-dimethylphenyl)acetamide
• CAS: 2011-57-6
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: JBGFEGSISUPAGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxy-2,3-dimethyl-phenyl)acetamide 在 palladium diacetate 、 copper(l) iodide 、 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 3-methoxy-1,2-dimethyl-9H-carbazole
  参考文献：
  名称：

  4-脱氧卡巴唑霉素 B 的合成：一种方便的替代品

  摘要：

  4-脱氧卡马霉素 B(3) 是通过 4-甲氧基-2,3-二甲基乙酰苯胺 (8) 与溴苯在碘化亚铜和碳酸钾存在下缩合，然后用 20% KOH 乙醇水溶液水解，然后环化合成的在乙酸中用乙酸钯得到取代的二苯胺(9)。

  DOI：

  10.1081/scc-100104069
• 作为产物：
  描述：

  二甲酚 在 盐酸 、 ammonium hydroxide 、 硫化氢 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 N-(4-hydroxy-2,3-dimethyl-phenyl)acetamide
  参考文献：
  名称：

  4-脱氧卡巴唑霉素 B 的合成：一种方便的替代品

  摘要：

  4-脱氧卡马霉素 B(3) 是通过 4-甲氧基-2,3-二甲基乙酰苯胺 (8) 与溴苯在碘化亚铜和碳酸钾存在下缩合，然后用 20% KOH 乙醇水溶液水解，然后环化合成的在乙酸中用乙酸钯得到取代的二苯胺(9)。

  DOI：

  10.1081/scc-100104069

文献信息

• Reaction of N-acetyl- and N-[1-(arylsulfonylimino)ethyl]-1,4-benzoquinone imines with sodium arenesulfinates
  作者：S. A. Konovalova、A. P. Avdeenko、V. V. Pirozhenko、O. P. Ledeneva、A. A. Santalova

  DOI：10.1134/s1070428014090097

  日期：2014.9

  N-Acetyl- and N-[1-(arylsulfonylimino)ethyl]-1,4-benzoquinone imines having no substituent in the 2- and/or 6-position of the quinoid ring react with sodium arenesulfinates preferentially according to the 1,4-addition pattern. The presence of an ArSO2N group favors radical ion reaction with formation of 1,6-addition products.

  根据1,4，在醌环的2-和/或6-位没有取代基的N-乙酰基和N- [1-（芳基磺酰亚胺基）乙基] -1,4-苯醌亚胺优先与芳烃亚磺酸钠反应-加法模式。ArSO 2 N基团的存在有利于自由基离子反应并形成1，6-加成产物。
• 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。
• 5-Aminocoumarans:  Dual Inhibitors of Lipid Peroxidation and Dopamine Release with Protective Effects against Central Nervous System Trauma and Ischemia
  作者：Shigenori Ohkawa、Kohji Fukatsu、Shokyo Miki、Tadatoshi Hashimoto、Junko Sakamoto、Takayuki Doi、Yasuo Nagai、Tetsuya Aono

  DOI：10.1021/jm960411j

  日期：1997.2.1

  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.
• Leuchs,D., Chemische Berichte, 1965, vol. 98, p. 1335 - 1341
  作者：Leuchs,D.

  DOI：——

  日期：——
• The fischer indolisation reaction and the synthesis of dihydroindenoindoles
  作者：David W. Brown、Mary F. Mahon、Aleyamma Ninan、Malcolm Sainsbury、Howard G. Shertzer

  DOI：10.1016/s0040-4020(01)81911-6

  日期：1993.1

  The Fischer reaction between indanones and certain alkoxyarylhydrazines fails; the indanones are returned unreacted and the arylhydrazines are converted into the corresponding alkoxy-2-chloroarylamines and other products. A new N-amination route to arylhydrazines from the arylamines has been developed and it has been demonstrated that problems with the indolisation of alkoxyarylhydrazones can be circumvented by ring closures of their O-tosylated analogues. Some results using the Lepke synthesis of indoles are recorded.