Ethyl 1-phenyl-5-[(triphenyl-lambda5-phosphanylidene)amino]imidazole-4-carboxylate | 1132702-97-6

• 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: Ethyl 1-phenyl-5-[(triphenyl-lambda5-phosphanylidene)amino]imidazole-4-carboxylate
• 英文别名: ethyl 1-phenyl-5-[(triphenyl-λ5-phosphanylidene)amino]imidazole-4-carboxylate
• CAS: 1132702-97-6
• 化学式: C₃₀H₂₆N₃O₂P
• 分子量: 491.529
• InChiKey: AHKCTUQKJBQNFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 1-phenyl-5-[(triphenyl-lambda5-phosphanylidene)amino]imidazole-4-carboxylate 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Sequential Three-Component Synthesis of 1,4-Bis[triazolo[4,5-d]pyrimidin-7(6H)-one]piperazines

  摘要：

  A simple three-component reaction and efficient method is described for the synthesis of 1,4-bis[triazolo[4,5-d]pyrimidin-7(6H)-one]piperazines by a sequential three-component process involving an aza-Wittig reaction/heterocyclization in the presence of sodium ethoxide as catalyst. The iminophosphorane 1 reacted with aromatic isocyanate gave carbodiimides 2, followed by addition of piperazine derivatives to give the corresponding guanidine intermediates 3. The guanidine intermediates were cyclized in the presence of catalytic amount of sodium ethoxide to give 1,4-bis[triazolo[4,5-d]pyrimidin-7(6H)-one]piperazines 4 in good yields.

  DOI：

  10.3987/com-12-12564
• 作为产物：
  描述：

  三苯基膦 、 ethyl 5-amino-1-phenyl-1H-imidazole-4-carboxylate 在 六氯乙烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到Ethyl 1-phenyl-5-[(triphenyl-lambda5-phosphanylidene)amino]imidazole-4-carboxylate
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of 1,2,9-trisubstituted 1,9-dihydro-6H-purin-6-ones

  摘要：

  The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with amines in the presence of a catalytic amount of RO Na+ to give the 1,2,9-trisubstituted 1,9-dihydro-6H-purin-6-ones 6 in good yields. Compound 6 exhibited cytotoxicity against various cancer cells. For example, compounds 6b showed the best inhibition activities against KB, HepG2 and OVCAR3 with IC50 9.5, 20.4 and 10.0 mu M. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.007

文献信息

• Sequential three-component synthesis of 1,4-bis[6,9-dihydro-6-oxo-9-phenyl-1<i>H</i>-purin-2-yl]piperazines
  作者：Zheng Dong Fang、Di Fang、Quan Cheng

  DOI：10.3184/174751912x13505755737168

  日期：2012.12

  synthesis of 1,4-bis[6,9-dihydro-6-oxo-9-phenyl-1H-purin-2-yl]piperazines by a domino three-component process involves an aza-Wittig reaction/heterocyclisation in the presence of sodium ethoxide as catalyst. Ethyl 1-phenyl-5-[(triphenylphosphoranylidene)amino]-1H-imidazole-4-carboxylate reacted with aromatic isocyanate to give carbodiimide intermediates, followed by addition of piperazines to give the

  一种通过多米诺三组分工艺合成 1,4-双 [6,9-二氢-6-氧代-9-苯基-1H-嘌呤-2-基]哌嗪的简单一锅高效方法涉及氮杂- 在乙醇钠作为催化剂存在下的 Wittig 反应/杂环化。1-苯基-5-[(三苯基亚膦基)氨基]-1H-咪唑-4-羧酸乙酯与芳香族异氰酸酯反应得到碳二亚胺中间体，然后加入哌嗪得到相应的胍中间体。胍中间体在催化量的乙醇钠存在下环化，以良好的收率得到 1,4-双（6,9-二氢-6-氧代-9-苯基-1H-嘌呤-2-基）哌嗪衍生物.
• Sequential Three-Component Synthesis of 1,4-Bis[triazolo[4,5-d]pyrimidin-7(6H)-one]piperazines
  作者：Zheng Dong Fang、Xian Hong Wei

  DOI：10.3987/com-12-12564

  日期：——

  A simple three-component reaction and efficient method is described for the synthesis of 1,4-bis[triazolo[4,5-d]pyrimidin-7(6H)-one]piperazines by a sequential three-component process involving an aza-Wittig reaction/heterocyclization in the presence of sodium ethoxide as catalyst. The iminophosphorane 1 reacted with aromatic isocyanate gave carbodiimides 2, followed by addition of piperazine derivatives to give the corresponding guanidine intermediates 3. The guanidine intermediates were cyclized in the presence of catalytic amount of sodium ethoxide to give 1,4-bis[triazolo[4,5-d]pyrimidin-7(6H)-one]piperazines 4 in good yields.
• Efficient synthesis and biological evaluation of 1,2,9-trisubstituted 1,9-dihydro-6H-purin-6-ones
  作者：Nian-Yu Huang、Yong-Ju Liang、Ming-Wu Ding、Li-Wu Fu、Hong-Wu He

  DOI：10.1016/j.bmcl.2008.12.007

  日期：2009.2

  The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with amines in the presence of a catalytic amount of RO Na+ to give the 1,2,9-trisubstituted 1,9-dihydro-6H-purin-6-ones 6 in good yields. Compound 6 exhibited cytotoxicity against various cancer cells. For example, compounds 6b showed the best inhibition activities against KB, HepG2 and OVCAR3 with IC50 9.5, 20.4 and 10.0 mu M. (C) 2008 Elsevier Ltd. All rights reserved.