2-苯基-5,6,7,8-四氢-4H-[1]苯并噻吩并[2,3-d][1,3]恶嗪-4-酮 | 73696-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-苯基-5,6,7,8-四氢-4H-[1]苯并噻吩并[2,3-d][1,3]恶嗪-4-酮
• 英文名称: 5,6,7,8-tetrahydro-2-phenyl-4H-benzo<4,5->thieno<2,3-d><3,1>-oxazin-4-one
• 英文别名: 2-Phenyl-5,6,7,8-tetrahydro-4H-<1>benzothieno<2,3-d><1,3>oxazin-4-on；2-phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]oxazine-4-one；2-Phenyl-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-on；2-phenyl-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-one；2-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d][1,3]oxazin-4-one
• CAS: 73696-35-2
• 化学式: C₁₆H₁₃NO₂S
• mdl: MFCD00424228
• 分子量: 283.351
• InChiKey: WCCHLKANERBZME-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C(Solv: ligroine (8032-32-4))
• 沸点：
  462.6±34.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-苯基-5,6,7,8-四氢-4H-[1]苯并噻吩并[2,3-d][1,3]恶嗪-4-酮 在 formamide 作用下， 反应 0.08h， 以90%的产率得到2-phenyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Synthesis of Some New Tetrahydrobenzo[b]thiophene Derivatives and Tetrahydrobenzothienopyrimidine Derivatives Under Microwave Irradiation

  摘要：

  2-Phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]oxazin-4-one (4) was reacted with either aliphatic or aromatic primary amines such as benzylamine, cyclohexylamine, p-toluidine, and/or p-anisidine to give carboxamide derivatives 5a-d, respectively. A bifunctional nucleophile such as ethanolamine was also reacted with 4, giving the carboxamide derivative 5e. Aminolysis of 4 with secondary amines such as piperidine and/or morpholine afforded the benzamide derivatives 6a and/or 6b, respectively. Fusion of 4 with hydrazine hydrate yielded the pyrimidine derivative 7 and carbohydrazide derivative 8. Thiation of 4 with phosphorous pentasulfide gave thienothiazine derivative 9, which reacted with benzylamine to give the pyrimidine derivative 10. Carbon nucleophiles such as ethyl cyanoacetate and/or malononitrile were subjected to react with 4 to give oxopropanoate 11 and/or oxopropanoic acid 12 derivatives, respectively. Microwave irradiation of 4 and formamide yielded the pyrimidinone derivative 13, which were subjected to react with phosphorous pentasulfide, a mixture of phosphorous oxychloride and phosphorous pentachloride and/or methyl iodide, to give 14, 15, and/or 16, respectively.

  DOI：

  10.1080/00397911.2010.501479
• 作为产物：
  描述：

  2-苯甲酰基氨基-4,5,6,7-四氢-1-苯并噻吩-3-羧酸 在 乙酸酐 作用下， 反应 5.0h， 以40%的产率得到2-苯基-5,6,7,8-四氢-4H-[1]苯并噻吩并[2,3-d][1,3]恶嗪-4-酮
  参考文献：
  名称：

  Synthesis of Some New Tetrahydrobenzo[b]thiophene Derivatives and Tetrahydrobenzothienopyrimidine Derivatives Under Microwave Irradiation

  摘要：

  2-Phenyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]oxazin-4-one (4) was reacted with either aliphatic or aromatic primary amines such as benzylamine, cyclohexylamine, p-toluidine, and/or p-anisidine to give carboxamide derivatives 5a-d, respectively. A bifunctional nucleophile such as ethanolamine was also reacted with 4, giving the carboxamide derivative 5e. Aminolysis of 4 with secondary amines such as piperidine and/or morpholine afforded the benzamide derivatives 6a and/or 6b, respectively. Fusion of 4 with hydrazine hydrate yielded the pyrimidine derivative 7 and carbohydrazide derivative 8. Thiation of 4 with phosphorous pentasulfide gave thienothiazine derivative 9, which reacted with benzylamine to give the pyrimidine derivative 10. Carbon nucleophiles such as ethyl cyanoacetate and/or malononitrile were subjected to react with 4 to give oxopropanoate 11 and/or oxopropanoic acid 12 derivatives, respectively. Microwave irradiation of 4 and formamide yielded the pyrimidinone derivative 13, which were subjected to react with phosphorous pentasulfide, a mixture of phosphorous oxychloride and phosphorous pentachloride and/or methyl iodide, to give 14, 15, and/or 16, respectively.

  DOI：

  10.1080/00397911.2010.501479

文献信息

• Functional derivatives of thiophene. XIX. Synthesis and biological activity of some esters of 2-benzoylaminothiophene-3-carboxylic acids
  作者：I. A. Kharizomenova、A. N. Grinev、N. V. Samsonova、N. V. Kaplina、M. V. Kapustina、G. N. Pershin、L. M. Polukhina、E. N. Padeiskaya

  DOI：10.1007/bf01152329

  日期：1980.12
• Ming, Yang-fu; Horlemann, Norbert; Wamhoff, Heinrich, Chemische Berichte, 1987, vol. 120, p. 1427 - 1432
  作者：Ming, Yang-fu、Horlemann, Norbert、Wamhoff, Heinrich

  DOI：——

  日期：——
• Achakzi, Darwizah; Ertas, Muemtaz; Appel, Rolf, Chemische Berichte, 1981, vol. 114, # 9, p. 3188 - 3194
  作者：Achakzi, Darwizah、Ertas, Muemtaz、Appel, Rolf、Wamhoff, Heinrich

  DOI：——

  日期：——
• Wamhoff, Heinrich; Ertas, Muemtaz, Angewandte Chemie, 1982, vol. 94, # 10, p. 800 - 801
  作者：Wamhoff, Heinrich、Ertas, Muemtaz

  DOI：——

  日期：——
• A new, general approach for the synthesis of heteroannulated 3,1-oxazin-4-ones
  作者：Heinrich Wamhoff、Stefan Herrmann、Stephan Stölben、Martin Nieger

  DOI：10.1016/s0040-4020(01)86261-x

  日期：1993.1

  Beta-(N-Triphenylphosphoranyliden)-enamino esters afford the synthetically useful heteroannulated 3,1-oxazin-4-ones with aroyl chlorides in different solvents. The reaction proceeds in one step and in high yields and appears to be independent of the reactivity of the heterocyclic substrate.