ethyl 3-phenyl-4-{[tri(phenyl)phosphanylidene]amino}-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxylate | 944443-28-1

• 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 3-phenyl-4-{[tri(phenyl)phosphanylidene]amino}-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxylate
• 英文别名: Ethyl 3-phenyl-2-sulfanylidene-4-[(triphenyl-lambda5-phosphanylidene)amino]-1,3-thiazole-5-carboxylate；ethyl 3-phenyl-2-sulfanylidene-4-[(triphenyl-λ5-phosphanylidene)amino]-1,3-thiazole-5-carboxylate
• CAS: 944443-28-1
• 化学式: C₃₀H₂₅N₂O₂PS₂
• 分子量: 540.646
• InChiKey: FPBBNYGVXMWRSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  37
• 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：
  99.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-phenyl-4-{[tri(phenyl)phosphanylidene]amino}-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxylate 在 sodium ethanolate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-diethylamino-3,6-diphenyl-2-thioxo-2,3,6,7-tetrahydrothiazolo[4,5-d]pyrimidin-7-one
  参考文献：
  名称：

  A facile synthesis of novel thiazolo[4,5-d]pyrimidin-7-ones

  摘要：

  Abstract Sixteen 5‐alkylamino‐3,6‐diaryl‐2‐thioxo‐2,3,6,7‐tetrahydrothiazolo[4,5‐d]pyrimidin‐7‐ones 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p were designed and easily synthesized via a tandem aza‐Wittig reaction. The iminophosphorane 2, obtained from reaction of 1 with triphenylphosphine, hexachloroethane and Et3N, reacted with aromatic isocyanate to give carbodiimide 3. carbodiimide 3 reacted with alkylamines to provide the title compounds in 45–61% isolated yields in presence of catalytic amount of ethoxide. The structures of compounds 4 were confirmed by 1H NMR, IR, MS, and elemental analysis. J. Heterocyclic Chem., 2011.

  DOI：

  10.1002/jhet.515
• 作为产物：
  描述：

  三苯基膦 、 2-硫代-3-苯基-4-氨基噻唑-5-甲酸乙酯 在 六氯乙烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 以98.5%的产率得到ethyl 3-phenyl-4-{[tri(phenyl)phosphanylidene]amino}-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  新型含氟噻唑并[4,5 - d ]嘧啶-7（6H）-的合成与除草活性

  摘要：

  设计了十八种新颖的5-烷基氨基-6-芳基-3-苯基-2-硫代-2,3-二氢噻唑并[4,5 - d ]嘧啶-7（6H）-酮5a–r，并通过串联氮杂容易地合成-维蒂希反应。用芳族异氰酸酯处理亚氨基磷烷2得到碳二亚胺3，该碳二亚胺3与氟取代的烷基胺反应，以乙醇钠为催化剂，标题化合物的分离产率为65-87％。所有化合物5均通过IR，1 H NMR，MS和元素分析确认，化合物5p通过单晶X射线衍射进一步分析。初步的生物测定结果表明，在100 mg / L的剂量下，某些化合物对油菜和grass草的根部生长表现出显着的抑制作用。

  DOI：

  10.1016/j.jfluchem.2007.04.011

文献信息

• A facile synthesis and herbicidal activities of novel fluorine-containing thiazolo[4,5-d]pyrimidin-7(6H)-ones
  作者：Ying Liang、Shuang Fan、Wen Yan Mo、Hong Wu He

  DOI：10.1016/j.jfluchem.2007.04.011

  日期：2007.7

  Eighteen novel 5-alkylamino-6-aryl-3-phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-7(6H)-ones 5a–r were designed and easily synthesized via a tandem aza-Wittig reaction. Treatment of iminophosphorane 2 with aromatic isocyanate gave carbodiimide 3, which reacted with fluoro-substituted alkylamines to provide the title compounds in 65–87% isolated yields using sodium ethoxide as catalyst. All compounds

  设计了十八种新颖的5-烷基氨基-6-芳基-3-苯基-2-硫代-2,3-二氢噻唑并[4,5 - d ]嘧啶-7（6H）-酮5a–r，并通过串联氮杂容易地合成-维蒂希反应。用芳族异氰酸酯处理亚氨基磷烷2得到碳二亚胺3，该碳二亚胺3与氟取代的烷基胺反应，以乙醇钠为催化剂，标题化合物的分离产率为65-87％。所有化合物5均通过IR，1 H NMR，MS和元素分析确认，化合物5p通过单晶X射线衍射进一步分析。初步的生物测定结果表明，在100 mg / L的剂量下，某些化合物对油菜和grass草的根部生长表现出显着的抑制作用。
• One-Pot Three-Component Synthesis of 1,4-bis[thiazolo[4,5-d]pyrimidin-7(6<i>H</i>)-one]piperazine derivatives
  作者：Zheng Dong Fang、Xian Hong Wei

  DOI：10.3184/174751912x13460803277147

  日期：2012.10

  A simple one-pot efficient method is described for the synthesis of 1,4-bis[thiazolo[4,5-d]pyrimidin-7(6H)-one] piperazine derivatives by a domino three-component process involving an aza-Wittig reaction/heterocyclisation in the presence of sodium ethoxide as catalyst. Ethyl 4-[(triphenylphosphanylidene)amino]-2,3-dihydro-3-phenyl-2-thioxothiazole-5-carboxylate reacted with aromatic isocyanates to

  描述了一种简单的一锅高效方法，用于通过涉及 aza-Wittig 的多米诺三组分工艺合成 1,4-双[噻唑并[4,5-d]嘧啶-7(6H)-one]哌嗪衍生物在乙醇钠作为催化剂存在下反应/杂环化。4-[(triphenylphosphanylidene)amino]-2,3-dihydro-3-phenyl-2-thioxothiazole-5-carboxylate 乙基 4-[(triphenylphosphanylidene)amino]-2,3-dihydro-3-phenyl-2-thioxothiazole-5-carboxylate 与芳香异氰酸酯反应得到碳二亚胺中间体。然后加入哌嗪以得到相应的胍中间体。然后在催化量的乙醇钠存在下将胍中间体环化，以良好的产率得到1,4-双[噻唑并[4,5-d]嘧啶-7(6H)-酮]哌嗪衍生物。
• A facile synthesis of novel thiazolo[4,5-d]pyrimidin-7-ones
  作者：Ying Liang、Hong-Wu He、Zi-Wen Yang

  DOI：10.1002/jhet.515

  日期：2011.1

  Abstract Sixteen 5‐alkylamino‐3,6‐diaryl‐2‐thioxo‐2,3,6,7‐tetrahydrothiazolo[4,5‐d]pyrimidin‐7‐ones 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p were designed and easily synthesized via a tandem aza‐Wittig reaction. The iminophosphorane 2, obtained from reaction of 1 with triphenylphosphine, hexachloroethane and Et3N, reacted with aromatic isocyanate to give carbodiimide 3. carbodiimide 3 reacted with alkylamines to provide the title compounds in 45–61% isolated yields in presence of catalytic amount of ethoxide. The structures of compounds 4 were confirmed by 1H NMR, IR, MS, and elemental analysis. J. Heterocyclic Chem., 2011.