[9-(4-bromobenzoyl)-6-(4-bromophenyl)-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-8-ylidene]acetonitrile | 748815-96-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [9-(4-bromobenzoyl)-6-(4-bromophenyl)-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-8-ylidene]acetonitrile
• 英文别名: (2E)-2-[9-(4-bromobenzoyl)-6-(4-bromophenyl)-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-8-ylidene]acetonitrile
• CAS: 748815-96-5
• 化学式: C₂₃H₁₇Br₂N₃O
• 分子量: 511.215
• InChiKey: CURJEFADDAONQC-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [9-(4-bromobenzoyl)-6-(4-bromophenyl)-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-8-ylidene]acetonitrile 以 乙腈 为溶剂， 反应 10.0h， 以52%的产率得到9-bromo-5-(4-bromophenyl)-12-oxo-1,3,4,12-tetrahydro-2H-1,4a-diaza-benzo[a]anthracene-7-carbonitrile
  参考文献：
  名称：

  Synthesis of annelated [a]aza-anthracenones and thieno[3,2-g]aza-naphthalenones through ring transformation of 2H-pyran-2-one followed by photocyclization

  摘要：

  A concise synthesis of some new classes of heterocycles (4-aryl-11-oxo-1,2,3,11-tetrahydro-1,3a-diaza-cyclopenta[a]anthracen-6-carbonitriles and 5-aryl-12-oxo-1,3,4,12-tetrahydro-2H-1,4a-diazabenzo[a]anthracene-7-carbonitriles) has been developed by the ring transformation of suitably functionalized 2H-pyran-2-one with alpha-oxoketene cyclic animals to intermediates (8-aroyl-5-aryl-2,3-dihydro-1H-imidazo[1,2-a]pyridine-7-ylidene)-acetonitriles and (9-aroyl-6-aryl-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-8-ylidene)-acetonitriles followed by their photocyclization either in CHCl3 or acetonitrile. This reaction was further explored for the synthesis of methyl 4-aryl-11-oxo-1,2,3,11-tetrahydro-1,3a,9-triaza-cyclopenta[a]anthracene-6-carboxylate, 4-aryl-11-oxo-1,2,3,11-tetrahydro-1,3a,9-triaza-cyclopenta[a]anthracene-6-carbonitriles, 5-aryl-12-oxo-1,3,4,12-tetrahydro-2H-1,4a,10-triazabenzo[a]anthracene-7-carbonitriles, 4-aryl-10-oxo-1,2,3,10-tetrahydro-9-thia-1,3a-diazadicyclopenta[a,g]naphthalene-6-carbonitriles and 5-aryl-11-oxo-1,3,4,11-tetrahydro-2H-10-thia-1,4-adiazacyclopenta[b]phenanthrene-7-carbonitriles from the similar reactions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.012
• 作为产物：
  描述：

  1-(4-溴苯基)-3,3-双甲基磺酰基丙酮 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 [9-(4-bromobenzoyl)-6-(4-bromophenyl)-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-8-ylidene]acetonitrile
  参考文献：
  名称：

  Synthesis of annelated [a]aza-anthracenones and thieno[3,2-g]aza-naphthalenones through ring transformation of 2H-pyran-2-one followed by photocyclization

  摘要：

  A concise synthesis of some new classes of heterocycles (4-aryl-11-oxo-1,2,3,11-tetrahydro-1,3a-diaza-cyclopenta[a]anthracen-6-carbonitriles and 5-aryl-12-oxo-1,3,4,12-tetrahydro-2H-1,4a-diazabenzo[a]anthracene-7-carbonitriles) has been developed by the ring transformation of suitably functionalized 2H-pyran-2-one with alpha-oxoketene cyclic animals to intermediates (8-aroyl-5-aryl-2,3-dihydro-1H-imidazo[1,2-a]pyridine-7-ylidene)-acetonitriles and (9-aroyl-6-aryl-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-8-ylidene)-acetonitriles followed by their photocyclization either in CHCl3 or acetonitrile. This reaction was further explored for the synthesis of methyl 4-aryl-11-oxo-1,2,3,11-tetrahydro-1,3a,9-triaza-cyclopenta[a]anthracene-6-carboxylate, 4-aryl-11-oxo-1,2,3,11-tetrahydro-1,3a,9-triaza-cyclopenta[a]anthracene-6-carbonitriles, 5-aryl-12-oxo-1,3,4,12-tetrahydro-2H-1,4a,10-triazabenzo[a]anthracene-7-carbonitriles, 4-aryl-10-oxo-1,2,3,10-tetrahydro-9-thia-1,3a-diazadicyclopenta[a,g]naphthalene-6-carbonitriles and 5-aryl-11-oxo-1,3,4,11-tetrahydro-2H-10-thia-1,4-adiazacyclopenta[b]phenanthrene-7-carbonitriles from the similar reactions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.012

文献信息

• An innovative approach to the synthesis of annelated [ a ]diaza-anthracenones through tandem cyclization
  作者：Ashoke Sharon、Prakas R Maulik、Raja Roy、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2004.06.015

  日期：2004.7

  An innovative route for the synthesis of a novel class of 4-aryl-11-oxo-1,2,3,11-tetrahydro-1,3a-diazacyclo-penta[a]anthracene-6-carbonitriles 5a-h and 5-aryi-12-oxo-1,3,4,12-tetrahydro-2H-1,4a-diazabenzo[a]anthracene-7-carbonitriles 5i-k has been developed by ring transformation of suitably functionalized 2H-pyran-2-ones 1 with alpha-oxoketene cyclic aminals 2 to give compounds 4 followed by photo-induced cyclization. (C) 2004 Elsevier Ltd. All rights reserved.