5-(buta-1',3'-dienyl)-2,3-diphenylpyrimidin-4(3H)-one | 214912-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(buta-1',3'-dienyl)-2,3-diphenylpyrimidin-4(3H)-one
• 英文别名: 5-[(1E)-buta-1,3-dienyl]-2,3-diphenylpyrimidin-4-one
• CAS: 214912-61-5
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: GBKJTGVYNMQGRQ-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-methoxyphenyl)-[1-(4-methoxyphenyl)meth-(E)-ylidene]amine 、 5-(buta-1',3'-dienyl)-2,3-diphenylpyrimidin-4(3H)-one 在 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到5-{2-[6-methoxy-2-(4-methoxyphenyl)quinolin-4-yl]vinyl}-2,3-diphenyl-3H-pyrimidin-4-one
  参考文献：
  名称：

  路易斯酸促进无环未活化的5-二烯基嘧啶酮与N-芳胺的氮杂Diels-Alder反应：新型喹啉衍生物的合成

  摘要：

  据报道，在路易斯酸催化剂存在下，5-二烯基嘧啶酮与N-芳胺的化学选择性和区域选择性氮杂Diels-Alder反应产生了新的喹啉衍生物。

  DOI：

  10.1016/j.tetlet.2007.01.129
• 作为产物：
  描述：

  1-phenyl-4-dimethylamino-2-phenyl-1,3-diazabutadiene 、 山梨酸氯化物 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-(buta-1',3'-dienyl)-2,3-diphenylpyrimidin-4(3H)-one
  参考文献：
  名称：

  Synthesis of 5-dienyl pyrimidinones and tandem [1,5] shifts in [4+2] cycloadditions of 1,3-diazabuta-1,3-dienes with butadienylketene

  摘要：

  The reactions of 1-aryl-2-phenyl-4-methylthio-4-secondaryamino / 4-N-allyl-N-aryl amino-1,3-diazabuta-1,3-dienes 1 with butadienylketene leading to a mixture of 5-dienyl pyrimidinones 4 and 5-butenyl pyrimidinones 6 are reported. Tandem [1.5]H and [1,5]SMe shifts are invoked to explain the formation of pyrimidinones 6. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01553-6

文献信息

• Lewis acid promoted aza Diels–Alder reactions of acyclic unactivated 5-dienyl pyrimidinones with N-arylimines: synthesis of novel quinoline derivatives
  作者：Gaurav Bhargava、Vipan Kumar、Mohinder P. Mahajan

  DOI：10.1016/j.tetlet.2007.01.129

  日期：2007.3

  The chemo- as well as regioselective aza Diels–Alder reactions of 5-dienyl pyrimidinones with N-arylimines in the presence of a Lewis acid catalyst resulting in novel quinoline derivatives are reported.

  据报道，在路易斯酸催化剂存在下，5-二烯基嘧啶酮与N-芳胺的化学选择性和区域选择性氮杂Diels-Alder反应产生了新的喹啉衍生物。
• Tandem sigmatropic shifts in [4 + 2] cycloaddition reactions of 1,3-diazabuta-1,3-dienes with butadienylketene: synthesis of pyrimidinone derivatives
  作者：Arun K. Sharma、S. Jayakumar、Maninder S. Hundal、Mohinder P. Mahajan

  DOI：10.1039/b109922c

  日期：2002.3.8

  The reactions of 4-dialkylamino substituted 1,3-diazabuta-1,3-dienes 1 with butadienylketene 2, are shown to undergo [4 + 2] cycloadditions to yield 5-(buta-1′,3′-dienyl)pyrimidinone 4 and tandem [1,5]H and [1,5]SCH3 shifts are shown to accompany the [4 + 2] cycloaddition reactions of 4-dialkylamino-4-methylthio substituted 1,3-diazabuta-1,3-dienes 5 with 2. The regioselective reactions of N-arylamino-1,3-diazabuta-1,3-dienes 11 and 14 with butadienylketene 2 are reported to yield 5-(buta-1′,3′-dienyl)-2-dialkylaminopyrimidin-4(3H)-one 13 and a mixture of 5-(buta-1′,3′-dienyl)-2-methylthiopyrimidin-4(3H)-one 17, 2-methylthio-5-[1′-(N-phenylamino)but-2′-enyl]pyrimidin-4(3H)-one 19 and 2-methylthio-5-[3′-(N-phenylamino)but-1′-enyl]pyrimidin-4(3H)-one 20, respectively. Tandem [1,5]H, [1,3]NHPh and [1,5]NHPh shifts are involved in the formation of pyrimidinones 19 and 20. The Diels–Alder reactions of the 5-dienylpyrimidinones with dimethyl acetylenedicarboxylate (DMAD) and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) yielded corresponding cycloadducts.

  4- 二烷基氨基取代的 1,3-二氮杂吲哚-1,3-二烯 1 与丁二烯酮 2 发生[4 + 2]环加成反应，生成 5-(丁-1′、3′-二烯基）嘧啶酮 4，并显示 4-二烷基氨基-4-甲硫基取代的 1,3-二氮杂-1,3-二烯 5 与 2 的[4 + 2]环加成反应伴随着串联[1,5]H 和[1,5]SCH3 迁移。据报道，N-芳基氨基-1,3-二氮杂吲哚-1,3-二烯 11 和 14 与丁二烯基酮 2 发生了区域选择性反应，生成了 5-(丁-1′,3′-二烯基)-2-二烷基氨基嘧啶-4(3H)-酮 13 和 5-(丁-1′,3′-二烯基)-2-二烷基氨基嘧啶-4(3H)-酮的混合物、3′-二烯基）-2-甲硫基嘧啶-4(3H)-酮 17、2-甲硫基-5-[1′-(N-苯基氨基)丁-2′-烯基]嘧啶-4(3H)-酮 19 和 2-甲硫基-5-[3′-(N-苯基氨基)丁-1′-烯基]嘧啶-4(3H)-酮 20 的混合物。[1,5]H、[1,3]NHPh 和 [1,5]NHPh 串联转变参与了嘧啶酮 19 和 20 的形成。5-二烯基嘧啶酮与乙炔二甲酸二甲酯（DMAD）和 4-苯基-1,2,4-三唑啉-3,5-二酮（PTAD）的 Diels-Alder 反应生成了相应的环加载产物。
• Lewis acid promoted imino Diels–Alder reactions of 5-dienyl pyrimidinones with N-aryl/naphthyl imines: synthesis of novel quinoline/benzoquinoline derivatives
  作者：Gaurav Bhargava、Chander Mohan、Mohinder P. Mahajan

  DOI：10.1016/j.tet.2008.01.041

  日期：2008.3

  The chemo- as well as regioselective imino Diels–Alder reactions of 5-dienyl pyrimidinones with N-aryl as well as N-naphthyl imines in the presence of a different Lewis acid catalysts resulting in novel quinoline and benzoquinoline derivatives are reported.

  据报道，在不同的路易斯酸催化剂存在下，5-二烯基嘧啶酮与N-芳基以及N-萘亚胺的化学和区域选择性亚氨基Diels-Alder反应导致了新的喹啉和苯并喹啉衍生物。
• Synthesis of 5-dienyl pyrimidinones and tandem [1,5] shifts in [4+2] cycloadditions of 1,3-diazabuta-1,3-dienes with butadienylketene
  作者：Arun K Sharma、S Jayakumar、Mohinder P Mahajan

  DOI：10.1016/s0040-4039(98)01553-6

  日期：1998.9

  The reactions of 1-aryl-2-phenyl-4-methylthio-4-secondaryamino / 4-N-allyl-N-aryl amino-1,3-diazabuta-1,3-dienes 1 with butadienylketene leading to a mixture of 5-dienyl pyrimidinones 4 and 5-butenyl pyrimidinones 6 are reported. Tandem [1.5]H and [1,5]SMe shifts are invoked to explain the formation of pyrimidinones 6. (C) 1998 Elsevier Science Ltd. All rights reserved.